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Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast Windjammer Cruise Lines-Winter Harbor

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

A Morning in Maine-Rockland

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Sail Portland Maine-Portland

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Silverlining Sailing-Ogunquit

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Schooner Stephen Taber-Rockland

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

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VisitMaine.Net – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright VisitMaine.Net 2023 Images Courtesy Greg and Heather Burke unless otherwise noted.

Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

sailboat tours maine

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

sailboat tours maine

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

sailboat tours maine

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

Best ever bucket list item! Absolutely wonderful Captain & Crew which made the whole experience a 5 star bucket list event for me. Sailing on an antique vessel was thrilling and boy could the crew make her preform!

sailboat tours maine

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

USA Today 2017 Readers' Choice Award - 10 Best

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The Schooner Surprise

Our 37th Year in Camden!

Celebrating our 105th anniversary 1918-2023, on the national register of historic places, schooner surprise.

Book Online Now!

Day trips :

Join us for a two hour daysail on the elegant Schooner Surprise out of Camden, Maine. We sail around the magnificent Penobscot Bay. On our Camden day cruises we will see lighthouses, wildlife, private yachts and summer estates. We offer Sunset sails, Tuesday night Sunset sails with live music, Full moon sails and Fireworks sails. We sail 7 days a week from mid May to mid October. Get involved and help raise sails or steer the boat, we are great with kids! Come and join us for a cruise on board the most famous windjammer in Maine. We offer environmentally friendly boat tours. We have limited amount of passengers with cushioned seating for all. Come sail the Maine Coast with us.

See our schedule and rates

Private Charters :

Join us for your Camden Maine Charter on the Schooner Surprise. Special events, weddings, birthdays, family reunions, anniversaries and corporate  events. Two hour, half day and full day cruises on the beautiful coast of Maine. Have us cater your Camden cruise and serve exquisite appetizers on a sunset sail or a lobster lunch. Our Maine windjammer cruises will give you an unparalleled view of Camden Hills. We have been highly rated tour operators in Camden Maine for 35 years. Rated #1 on Trip Advisor!! Book your Camden Charters with us.

Learn more about private charters on the Schooner Surprise

Special Events

Full moon sail with live music.

Watch the sunset over Camden Hills and the full moon rise over Penobscot Bay.

June 21 (7:15pm - 9:15pm) July 20 (7:15pm - 9:15pm) August 18, 19 (7:15pm - 9:15pm) Rate: Adults $65 / Kids $47

September 17 (5:30pm - 7:30pm) Rate: Adults $65 kids $50

Fireworks over Camden Harbor

July 4 7:15pm - 9:15pm Rate: Adults/Kids $76

September 30 7:30pm - 9:30pm Rate: Adults/Kids $75

Sunset Sail with Live Music

Watch the sunset over Camden Hills and listen to live acoustic music.

July 1, 3, 5, 8, 10, 12, 15, 17, 22, 24, 26, 29, 31 (7:15pm - 9:15pm)

August 2, 5, 7, 9 (7:15pm - 9:15pm)

August 12, 14, 16, 19, 21, 23, 26, 28, 30 (5:15pm - 7:15pm)

Rate: Adults $71 / Kids $62

Birding and Marine life tour with ornithologist Richard Podolsky

July 2, 3, 4, 9, 10, 11, 16, 17, 18, 23, 24, 25, 30, 31 (10am - 12pm)

August 1, 6, 7, 8, 13, 14, 15, 20, 21, 22, 27, 28, 29 (10am - 12pm)

Rate: Adults $65 / Kids $60

Check out our sister ship!

Contact Us:

Schooner Surprise Ramiro and Nicole de Acevedo Ramos 207.236.4687 1 Bay View Street Camden, ME 04843

[email protected]

Sloop Anjacaa

Check out our sister ship: Sloop Anjacaa

Camden Rockland Maine  Chamber of Commerce Camden, Lincolnville, Maine Inns, B&B’s and Hotels Rockland, Rockport, Maine Inns, B&B’s and Hotels Vacation Rentals Camden Maine Weather Schooner Surprise Trip Advisor Schooner   Surprise Facebook Page Schooner Surprise Yelp Schooner Surprise Instagram Down East Magazine Maine Magazine Penbscot Bay Pilot Web News Maine Boats, Home and Harbors website

We look forward to sailing with you again in May 2024.

A Morning in Maine

A Morning in Maine

Sailing tours on beautiful penobscot bay, featured sailing trips.

  • Most Popular!
  • Clock 2 Hours
  • Users All Ages

2-Hour Sailing Trip

Join Captain Tyler Waterson aboard the beautiful 55′ ketch Morning In Maine, as he points out the natural and historic features unique to Penobscot Bay.

  • Clock 6 Hours

Monroe Island Adventure

Your island adventure awaits! Maine has over 3,000 miles of coastline, and almost half of that is on islands only accessible by boat.

  • Clock 2.5 Hours

Science under Sail

Join us and a science educator from our partners at Herring Gut Coastal Science Center in Port Clyde as we set sail to learn about the ecology of Penobscot Bay!

Day Sails on Penobscot Bay

Enjoy the Maine Coast’s beauty from the deck of Morning In Maine. Relax and watch the seabirds and harbor seals as the ketch glides through the waters of Penobscot Bay… or lend a hand in sailing the boat!

On most Maine sailing trips we see Rockland Breakwater Lighthouse, Owls Head Lighthouse, and historic schooners. Monday morning is the best time for a day sail in Rockland, Maine, where we watch the schooners sail out of the harbor for their week-long cruises.

people sailing on a boat

We look forward to having you aboard!

The boat accommodates 21 passengers and can fill up quickly, so make your reservations early!

#1 Outdoor Activity in Rockland, Maine! Our Customers Love Us!

Maine is best by sailboat.

“Loved our afternoon on Morning in Maine. The wind was great and the boat is really lovely. Capt Tyler and George were great crew. Saw eagles, a harbor seal and all the sights you’d want to see in Rockland. Sailing really is the best way to get to know Maine.”

Best "boat ride" in Maine

“As Mainers, we have had the opportunity to go on various “boating adventures” along the Maine coast. This was the most pleasant and fun one ! 2 hours was perfect. The captain allowing the kids to help with the sails was very cool and even steer… Totally made their day. The captain was very personable and made the trip interesting. I was concerned about getting seasick, but the ride was actually very smooth.”

“We had a wonderful time on our sailing expedition and learned a lot about the area. Definitely worth the time to spend some time on the water with folks that live in the area sharing lots of good stories.”

Great experience!

"Our sail on a Morning in Maine was one of the highlights of our trip. The views were beautiful and the ride was smooth and relaxing. It was a great experience and one that I highly recommend!"

Sail Acadia

SAIL ACADIA

Sailing charters & lobster tours at acadia national park.

  • Most Popular Tour

Mount Desert Island Sailing Tour

Sail Acadia National Park aboard a traditional Friendship Sloop – Maine’s original lobster boat! Built in Friendship, Maine in the late 1800’s, these handsome traditional sailboats were used by coastal fishermen to haul lobster traps by hand under sail. Take part in Maine’s maritime heritage and enjoy sailing smooth waters, abundant wildlife and spectacular coastline of Acadia National Park.

  • Info Up to 6 passengers
  • User All Ages
  • Hour Glass 2 - 3 Hours
  • Great for Families!

Lobster & Nature Tour

Enjoy a nature cruise aboard the Elizabeth T, a real Maine lobster boat! Haul lobster traps, visit Somes Sound, and see a seal colony on a perfect size boat for sightseeing, island picnics, and lobster fishing demonstrations.

  • Info Shared Tours are up to 16 passengers; Private Charters are up to 21 passengers
  • Hour Glass 2 Hours

sailboat tours maine

Sail Acadia National Park

Escape the crowds of Bar Harbor and explore the spectacular coastline of Acadia National Park.

Sail aboard a classic Friendship sloop or a real Maine lobster boat for a private or shared tour of Maine’s most beautiful coastline along Mount Desert Island.

Sailing and lobster boat cruises depart several times each day from Southwest Harbor and Northeast Harbor, just 15 – 20 minutes from Bar Harbor.

At Sail Acadia we maintain and operate our locally built wooden boats with a great respect for Maine’s maritime heritage. We believe in smaller groups and personalized attention for an authentic boating experience in Acadia. Our captains and crew will share their local knowledge and give you their best tour of Mount Desert Island.

sailboat tours maine

Five-Star Sailing & Boat Tours ★★★★★

Sail Acadia

We were blown away by the service at Sail Acadia. We did a mid-morning private tour for 7 of us. We were able to bring our own mimosas :) Our captain and first mate were knowledgeable, inviting, friendly and easy going. They were very welcoming to our pup! They had blankets and cups on board. Definitely recommend!

We thoroughly enjoyed our sunset cruise with Mike and Kelly. Mike told some great stories of the area, we took wine and dinner to have on the boat, and we enjoyed seeing guillemots and porpoises in the bay. The wind was very light that evening so we had to motor a bit, but it was such a treat to be out on the water on a 120 year old wooden sail boat. We loved it!

We booked a 3 hour sunset sail and it was so much fun. It wasn't the windiest day, but being on the water on a beautiful summer night watching the sun go down can't be beat. We saw plenty of porpoises and other sea wildlife throughout the ride. Bonus points: the tour is BYOB so we brought a bottle of wine with us and the crew provided cheese, crackers and snacks. Thanks for having us!

An awesome experience we can't recommend more highly. Not only was it a fantastic sailing experience, the crew were informative about the area, history, wildlife and the things we were seeing along the way. The crew was great, the boat charming and historic. The best afternoon we have had in Maine for as long as we can remember!

Ambergris Voyages

Ambergris Voyages

Acadia national park boat tours in maine, our acadia national park boat tours.

  • most popular!

Sunset Sail

End your day on a high note by watching the sunset over Mount Desert Island from the sea. As the day winds down, the sea breeze typically subsides, creating a peaceful sailing experience with stunning views of Acadia National Park. Book your sail online!

  • Hour Glass 3 hours
  • User All ages

Afternoon Sail

The afternoon is usually the windiest, providing a brisk sail to take us further afield. Depending on the wind direction, we may head to the Cranberry Islands, out the Western Way, or up Somes Sound. Book online today!

Morning Sail

This summer, we’ll be sailing from our home port of Southwest Harbor, Maine. Let us show you why we love this place so much! There is no set route, we sail according to the wind and your interests.

Our Sailing Charters

Welcome aboard the ambergris.

We invite you to embark on an unforgettable sailing charter aboard a traditional schooner in the stunning Acadia National Park. Departing from Southwest Harbor, Maine, our sailing tour offers a unique opportunity to explore the pristine waters and breathtaking landscapes of this renowned national park and the Bar Harbor region. Our majestic boat rides in Maine are waiting for you to complete your historic New England experience! Book your Acadia boat tours with us online today.

The Ambergris

The Ambergris’ design is based on a Pinky Schooner, a New England boat that was used in the 1800s for fishing and hauling cargo. She’s 60 feet on deck and 80 feet overall. We only take six passengers, so there’s plenty of room on her wide decks to enjoy the sail. Join us for a lovely Maine sailing trip today!

Ambergris’ Story

Captain Patrick Reilly was a sailor in search of a ship.

He had grown up sailing in Maine and started working boats as a teenager. By the time he was 18, he had earned his USCG captain’s license and started working as a yacht captain, sailing all over the world. He also had several boats of his own, the latest of which he had recently sold in Central America.

He found the Ambergris in Florida where she had been lying for the past 10 years. She was a bare hull with a half-rotten foremast, but her steel construction was sound and with a lot of work Patrick saw that she would be a fine sea boat.

Patrick, his partner Erin and their friends motored the Ambergris over to the Bahamas for the rest of the winter where they scraped off the barnacles from her bottom, reinforced the rotten mast and built a jury rig to sail her back to Maine.

That summer they worked on new masts and rigging for the Ambergris, making her seaworthy before sailing back to the Caribbean. Since then they have sailed thousands of more miles aboard the Ambergris between the Caribbean and her summer home in Maine.

a close up of a boat

How We Board the Ambergris for the Acadia Boat Tour

The Ambergris will be waiting for us on her mooring out in the harbor. To get out to her, we’ll take our ship’s boat, which was originally a lifeboat for a fishing boat from Newfoundland. To get aboard the Ambergris, we’ll climb a short ladder up the ship’s side.

Please let us know if you have mobility issues and we’ll do our best to accommodate.

We’ll meet here. Our office at 172 Clark Point Road

a boat sitting on top of a wooden dock over some water

Sail into the Sunset on our Acadia Boat Tours! ★★★★★

Ambergris Voyages - Logo

Beautiful and relaxing. We went in the fall so the weather was perfect. I also loved the history behind the boat. Highly recommend!

Lovely sail with a lovely captain!

The four of us had the boat to ourselves with Patrick, our captain. One of us was an experienced sailor and enjoyed talking "shop" with Patrick. The boat is very stable and no chance of getting seasick. Lots of space to walk around the deck. Great way to spend the afternoon. Thank you Patrick!

Great trip!

Friendly captain. Good boat. All around fun ride. The weather was beautiful. The views were impressive. Good speed.

Excellent sail on a large craft!

We had an excellent sail though Somes Sound! Captain Patrick was a joy to chat with when the wind was light and the most adept sailing captain when the wind picked up! Highly recommend!

sail portland maine logo

Treat yourself to the best Portland, Maine boat charters with Sail Portland Maine. There is no better way to experience our vibrant city’s coastline!

Relax aboard our sailing vessel the Eleanor Hawkes, or our newly acquired picnic boat, the Calista Ann, as we cruise through tranquil waters of Portland Harbor sailing Casco Bay. Bring along any beverages and snacks you want, there are a myriad of eateries, breweries, and food trucks in Portland. Come enjoy the sights and sounds of our lovely Casco Bay and the Portland skyline and working waterfront.

Flappy Hour at Crown Jewel

Experience the ultimate Flappy Hour celebration on a chartered cruise to Crown Jewel, nestled on the picturesque shores of Great Diamond Island in Casco Bay. Click the image below to book your experience with Crown Jewel today!

island cruise portland maine

Our Custom Day and Sunset Charter Cruises

Every day we offer two-hour public or private charters that might have you cruising past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained and crewed excursions aboard our vessels, the Eleanor Hawkes or the Calista Ann. 

We provide multiple trip options to ensure that your Portland, Maine boat cruise fits into your schedule or the ability to customize times for a private charter. You can choose from three different charter times throughout the day:

Eleanor Hawkes (Sailboat) → Book a Sail on the Eleanor Hawkes

Public and Custom Private Charters Available. You’re welcome to bring your own food and beverages aboard.

  • 12:00 PM – 2:00 PM (Fall hours vary)
  •   3:00 PM – 5:00 PM (Fall hours vary)
  •   6:00 PM – 8:00 PM ( Fall hours vary )

Calista Ann (Classic Motor Yacht) → Book a Cruise on the Calista Ann

Public and Custom Private Charters Available. You’re welcome to bring your own food and beverage aboard.

  •   6:00 PM – 8:00 PM (Fall hours vary)

Private Charters → Book Your Private Charter

Private charters are based on availability..

Our private cruises are perfect for a group of up to 6 guests on the Eleanor Hawkes and up to 12 passengers on the Calista Ann . For even more space, book the Calista Ann – she is the newest addition to the company, keeping with the style and intimacy that our brand represents. She is a classic Downeast Picnic boat and is a comfortable cocktail cruiser. 

Private charters could be anything from a couple wanting to cruise to one of the nearby island restaurants for an anniversary dinner and then a cruise back under the stars, or a couple who wants to elope and get married by the captain with a few friends to witness – your imagination is the limit! We can recommend catering as well. 

Some of the many incredible island restaurants we can take you to by boat are Crown Jewel on Great Diamond Island, The Dolphin Marina & Restaurant or Iris Eats in Harpswell, and Island Lobster Company on Peaks Island.

Book Your Portland Maine Boat Tour!

When you book your ticket for one of our private chartered boat trips at Sail Portland Maine, it can be anything you want it to be! There are so many beautiful and unique factors about our beloved Casco Bay – from diverse wildlife like seals and porpoise to the historic Fort Gorges and the sun setting over coastal islands, soak in the beauty that is Portland’s harbor. For an incredible adventure you’ll talk about for years to come, reserve your trip with us below!

Book Your Sailing or Cruising Trip on the Waters of Casco Bay Now

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Maine Windjammer Cruises®

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Maine Windjammer Cruises

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Swift is a very special vessel designed in 1935 by Murray Peterson, a masterful naval architect famous for his coaster designs.  Originally intended as a luxury yacht, she was launched in 1983 after nearly twenty years of love and dedication to build her.

A diagram of Swift below decks and a more detailed description is on our Accommodations page.

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Imagine gliding past lighthouses, harbor seals and islands or enjoying the still waters and beautiful scenery of our lakes – a few hours on a boat in Maine’s waters is a relaxing and extraordinary experience. Whether it’s a Maine harbor tour, a sunset cruise, a lobster boat excursion, or a wildlife cruise – any boat tour in Maine will offer a unique and unforgettable experience.

There are numerous cruises and tours to choose from on a variety of vessels from cozy schooners to large tour boats and even historic riverboats. So, take a pick, book a tour and be ready to take in the sights along the way.

Maine Beaches

  • First Chance Whale Watch – scenic cruises and whale watches, Kennebunk
  • Rugosa Lobster Tours – lobster boat tours, Kennebunkport
  • Finestkind Scenic Cruises – scenic and lobster boat tours, Ogunquit

Portland & Casco Bay

  • Lucky Catch Cruises – scenic and lobster boat tours, Portland
  • Maine Duck Tours – land and sea historical tours, Portland
  • Portland Schooner Co. – windjammer sails, Portland
  • Portland Discovery Land & Sea Tours – lighthouse and nature cruises, Portland
  • River Run Tours – scenic cruises, Bath
  • Captain Dave’s Maine Photo Safaris - a photography and sightseeing tour, Richmond and MidCoast
  • Damariscotta River Cruises – oyster, wildlife and scenic cruises, Damariscotta
  • Cabbage Island Clambakes – boat rides and traditional lobster feeds, Boothbay Harbor
  • Cap'n Fish's Whale Watch – wildlife watching tours, Boothbay Harbor
  • Schooner Eastwind + Applejack – day sails, sunset sails, Boothbay Harbor
  • Balmy Days Cruises – boat and sailing tours and private charters, Boothbay Harbor
  • Hardy Boat Cruises – scenic cruises and wildlife watching tours, New Harbor
  • Monhegan Boat Line – nature cruises, Port Clyde
  • Bufflehead Sailing Charters – sailing charters, Rockland
  • Schooner Yacht Heron – windjammer sailing cruises, Rockland
  • Camden Harbor Cruises – lighthouse lobster tours, Camden
  • Schooner Appledore II – windjammer sailing cruises, Camden
  • Schooner Lazy Jack II – windjammer sailing cruises, Camden
  • Schooner Surprise – windjammer sailing cruises, Camden
  • Schooner Olad + Cutter Owl - windjammer sailing cruises, Camden
  • Castine Harbor Tours – local history cruise, Castine

DownEast & Acadia

  • Isle au Haut Boat Services – scenic and wildlife tours, Stonington
  • Bar Harbor Whale Watch Co. – whale watches, Bar Harbor
  • Lulu Lobster Boat Ride – lobster boat tours, Bar Harbor
  • Diver Ed – nature cruises, Bar Harbor
  • Downeast Windjammer Cruise Lines – windjammer sailing cruises, Bar Harbor
  • Robertson Sea Tours & Adventures – scenic and wildlife tours, Milbridge
  • Eastport Windjammers – windjammer cruises, Eastport
  • Downeast Charter Boat Tours – whale watching and wildlife tours, Lubec

Maine Lakes & Mountains

  • Songo River Queen II – scenic lake cruises, Naples

Kennebec Valley

  • Snow Pond Cruises – scenic lake cruises, Oakland
  • Katahdin Cruises – scenic lake cruises, Greenville
  • Twin Maple Outdoors - river and wildlife tours, Bradford

Businesses & Organizations

Acadian boat tours.

Relaxed boating trips with FREE onsite parking - visit us today!

Phone: (207) 801-2300

Website: www.acadianboattours.com

Address: 47 West St. , Bar Harbor

A Morning in Maine Sailing Tours

A Morning in Maine offers 2-hour sailing tours, sunset sail and private sailing events for up to 21 passengers out of Rockland Harbor.

Phone: 207-691-7245

Website: www.amorninginmaine.com

Address: Rockland Harbor, Middle Pier , Rockland

Authentic Leaf Peeping Nature Adventures with Twin Maple Outdoors

Leaf Peepeing Tours! Book Now for 2017/2018 season! Instagram Photos - https://www.instagram.com/twinmapleoutdoors/?hl=en

Phone: 207-907-9151

Website: www.twinmapleoutdoors.com

Address: 303 Williams Rd , Bradford

Authentic Maine Recreation Adventures with Twin Maple Outdoors

Maine Moose Watching Tours - Truck or boat tours Penobscot River Boat Tours Hikes (Waterfalls, Ice Caves) Hike, truck or boat Tramway - boat/hike Winter outback tour

Website: www.TwinMapleOutdoors.com

Baker Island / Acadia National Park adventure

Join an Acadia National Park ranger on this exciting cruise and adventure. We travel to Baker...

Phone: (207) 288-2386, 1-800-942-5374

Website: www.barharborwhales.com

Address: Bar Harbor Whale Watch Co. 1 West Street , Bar Harbor

Balmy Days Cruises

The day trip to Monhegan Island gives you everything you came to Maine to see: lighthouses, lobster...

Phone: 207-380-5416

Website: balmydayscruises.com

Address: 122 Lakeside Dr. , Boothbay Harbor

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Cabbage island clambake, ferry rides, 50 miles off shore (and still at home), get inspired at the maine quarterly, the light you keep, main street maine.

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Shore Excursions Group

Schooner Sail

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  • Glice past Frenchman Bay's rocky shores and islands aboard a classic schooner ship
  • Hoist the sails or take a turn at the wheel
  • Feel Bar Harbor's Downeast character
  • See the shores of Acadia National Park
  • Pack a picnic, then sit back and relax

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Bar Harbor, originally called Eden, has a world-renowned ambiance that blends seashore community, downeast character, rocky shores, and the famous Maine Lobster. Founded in 1796, it is the best-known town on Mount Desert Island.

Enjoy a peaceful, serene, and comfortable sail among the islands of Frenchman Bay aboard a classic schooner ship. Since the 1700s, schooners have been used for a variety of purposes because they are fast, sleek, adaptable, and considered the sturdiest ships of all time.

Frenchman Bay is named for Samuel de Champlain, the French explorer who visited the area in 1604. The bay is bounded on the east by the Schoodic Peninsula, and on the west by Mount Desert Island; parts of both are in Acadia National Park. It contains numerous islands, the largest of which is Ironbound Island. The bay extends for roughly 15 miles and spans 7 miles at its widest.

Pack a meal, bring your favorite non-alcoholic beverage, sit back and relax or, if you feel inspired, join the crew to hoist the sails or take a turn at the ship's wheel.

Please Note: Restroom facilities are available onboard for your convenience. In regards to weather, many different forecasts are monitored and will be considered when making a decision regarding cancellations. This tour is not necessarily cancelled for rain and/or fog. As the tour is designed to give guests the sailing experience in typical Maine weather.

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SEAGLASS SAILING CO.

We're Not Just Better, We're the Best

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S/V Seaglass, a 1965 Pearson Rhodes 41 turns heads everywhere she sails.  

The 41' masthead sloop can comfortably accommodate up to 6 passengers for 1/2 day, full day, and overnight voyages around Casco Bay.  

A comfortable cabin and spacious cockpit provide gracious space for relaxing and entertaining.  

Captain Paul Leddy, who grew up sailing the waters of Casco Bay, is looking forward to helping you plan an unforgettable Maine Experience.  

Contact us today, or learn more about voyages aboard S/V Seaglass .  

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Captain Paul and Seaglass Sailing Co. are here to share the beauty of Casco Bay and a passion for sailing with all of their visitors. Questions, comments or special requests? We’d love to hear from you, so don’t hesitate to reach out today.

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THE 10 BEST Maine Boat Tours

Boat tours in maine.

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  • The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

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1. 2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

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2. Windjammer Classic Sunset Sail

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3. Luxury Catamaran Sailing Charters in Maine

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4. Portland Tall Ship Cruise on Casco Bay

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5. Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

sailboat tours maine

6. Schooner Applejack Sunset Sail Tour in Boothbay Harbor

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7. Schooner Eastwind Sunset Sail to see the Maine Coastline

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8. Sunset Sailing Cruise

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9. Guided RIB Boat Adventure of Casco Bay

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10. Maine Whale Watching Tour in Portland

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11. Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

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12. Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

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13. Half Day Self-Guided Paddle

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14. Sunset Lighthouse Harbor Cruise from Portland's Old Port

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15. Windjammer Classic Day Sail from Camden, Maine

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16. Seven Portland Lighthouses Tour

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17. Midday Broadwater Sailing Cruise

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18. Private Sunset Charter on a Vintage Lobster Boat

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19. Half Day Kayak Rental on Sebago Lake

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20. 3 Hour Kayak/SUP Rental in Cape Porpoise Harbor

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21. 3 Hour Kayak/SUP Rental in Biddeford Pool

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22. Portland Tall Ship Private Charter on Casco Bay

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23. New England Fall Foliage Private Vintage Lobster Boat Cruise

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24. Mere Point Oyster Farm Tour

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Explore, Discover The Ocean

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine and Northern New England.

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Enjoy The Ocean With Your Family

NorthPoint Yacht Charters offers a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

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Charter with NorthPoint Yacht Charters

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events. We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free.

About NorthPoint Yacht Charters

NorthPoint Yacht Charters

Welcome to the 2024 Charter Season

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine, Northern New England and the Canadian Maritimes. We offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events.  We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free. 

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Luxury yachts.

Select from wide variety of boats including both power and sailboats 20-80 feet:

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KOAN performed beautifully. …. The engine runs great . MC
Our charter of Blue Goose two was excellent. She is the only boat I have ever charter or used including my own that there was nothing to fix. She was very clean, well outfitted with towels, linens and basic condiments.
We had a great cruise on Alliance. We visited Pulpit, Castine, NE Harbor, Seal Harbor (Vinalhaven), Islesboro and Tenants. RE

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NorthPoint Yacht Charters arranges sailing and power boat cruising charters, we offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

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21 Best Boat Tours in Maine

Best Boat Tours in Maine

Whether you live in Maine or you’re just visiting, a boat tour is a great way to see the sights. And if you’re looking for some suggestions on where to go, you’ve come to the right place!

We’re going to take a look at the 21 best boat tours in Maine. And we’ll show you options from all along the Maine coast.

So if you’re ready, let’s get started!

The Best Boat Tours in Maine

1. camden harbor cruises, camden.

Camden Harbor Cruises, Camden

There’s a choice of two vessels with Camden Harbor Cruises – M/V Lively Lady and M/V Periwinkle. Choose either option and you’ll see the beautiful coastline around Camden Harbor and Penobscot Bay.

Tours are child-friendly, and the little ones can get involved checking lobster pots. Adults will enjoy the seaside mansions, atmospheric lighthouses and grand visiting yachts.

It’s best to book ahead to secure your place. Some seats are in the shade – let them know in advance if you have a preference. There’s a flushable toilet on board too.

2. Hardy Boat Cruises, New Harbor

Hardy Boat Cruises, New Harbor

Based in New Harbor, award-winning Hardy Boat Cruises is a great choice to see Maine’s wonderful wildlife . They offer trips to see seals and puffins, as well as cruises to Moneghan Harbor and along the Maine coast.

Their puffin trip involves a 1.5-hour round trip out to Eastern Egg Rock to see the birds in their natural habitat. It’s fully narrated by a guide from the National Audubon Society and Project Puffin.

There’s also a 1-hour seal watching trip, and a 1.5-hour trip to Muscongus Bay with a stop to view the seals. In colder weather, warm drinks and blankets are provided too.

3. Lucky Catch Cruises, Portland

Lucky Catch Cruises, Portland

If you’d like to get a glimpse into the life of a Maine fisherman, check out Lucky Catch Cruises. They provide lobster tours to tell you all about these fascinating crustaceans – and how they get from sea to plate! You can even purchase whatever is caught on your trip for the freshest possible diner.

Each tour lasts between 80 and 90 minutes, and they depart four or five times a day. Opt for the Seal Watch tours to get the best chance of seeing some seals too.

4. Acadian Boat Tours, Bar Harbor

Acadian Boat Tours, Bar Harbor

If you’re looking for a tour from Bar Harbor, Acadian Boat Tours offer a brilliant selection. There are daytime cruises, sunset cruises, tours focusing on seabirds and those dedicated to lighthouses, small coastal towns and fjords.

You can also join in a fishing trip, or even charter a private tour with your very own captain. And if you’re there on Independence Day, there’s a special trip to see the fireworks from the water.

5. Portland Schooner Co., Portland

Portland Schooner Co., Portland

If you’ve ever dreamed of sailing on an elegant, old-time schooner, this is your chance to make it happen. Portland Schooner Co. offer sails on two elegant ships. Bagheera and Heart’s Desire are Alden schooners, dating from 1924 and 1925 respectively.

There are four trips every day – one in the morning, two in the afternoon, and one at sunset. And both boats are also available for private charters.

6. Robertson Sea Tours & Adventures, Milbridge

Robertson Sea Tours & Adventures, Milbridge

Robertson Sea Tours offer a great range of excursions on their 32-foot boat, the Kandi Leigh . Choose from puffin and seabird tours, lighthouse cruises, or lobster catching trips. You can also charter the boat for a private tour .

The number of trips each day depends on the season, and the lighthouse cruise runs only in September and October. Check out the website for an up-to-date schedule and online booking.

7. Cap’n Fish’s Cruises, Boothbay Harbor

Cap’n Fish’s Cruises, Boothbay Harbor

Cap’n Fish Cruises is based in Boothbay Harbor. Here the focus is very much on Maine’s fascinating wildlife, with the tour’s termed “sea-faris”.

Tours include the opportunity to see whales at Maine’s primary whale feeding grounds. You can also combine whale watching with a trip to Eastern Egg Rock to see puffins.

There are also some great options for history lovers. The Kennebec River Cruise tours 44 miles of the river, with a narration taking you back to its colonial past. And other tours focus on lighthouses and other local landmarks.

8. Lulu Lobster Boat Ride, Bar Harbor

Lulu Lobster Boat Ride, Bar Harbor

For a glimpse into the traditional lobster industry, there’s nothing quite like Lulu Lobster Boat Ride. Lulu is the only Downeast-style lobster boat giving tours from Bar Harbor, and it provides a unique experience.

The two-hour trips include hauling lobster traps, with an explanation of how it all works. And you can learn some fascinating facts about the life and biology of the Maine lobster. Also on offer are sightseeing and seal-watching trips.

Don’t worry about heading out in colder weather – blankets are provided to keep you snug and warm.

9. Finestkind Scenic Cruises, Ogunquit

Finestkind Scenic Cruises, Ogunquit

Finestkind Scenic Cruises are located in the picturesque Perkins Cove. They offer a choice of three different vessels carrying 37, 43 and 60 passengers respectively. And there’s also a traditional wooden-crafted sailboat, the Cricket, which has room for six people.

Choose from breakfast or cocktail cruises, scenic lighthouse cruises or lobstering trips. If you’re looking for tranquillity, opt for a sailing cruise on the Cricket. Powered by sail and oar, there’s no engine to disturb the peace and quiet – or the wildlife.

10. Damariscotta River Cruises, Damariscotta

Damariscotta River Cruises, Damariscotta

If you love oysters, you’ll love Damariscotta! The town is home to 80 percent of Maine’s farmed oysters. The two-hour tours take in everything you need to know about the oyster industry, and you can sample the produce whilst you’re on board!

All those tasty oysters also attract other wildlife. Expect to see harbor seals, bald eagles and ospreys on your tour.

You can combine your oyster tour with wine tasting, or a sunset cruise with cocktails. And in September and October, there are special tours to view the beauty of the Fall trees from the water.

11. Downeast Charter Boat Tours, Lubec

Downeast Charter Boat Tours, Lubec

Downeast Charter Boat Tours in Lubec offer trips to see some spectacular sights.

One of the most unusual is “Old Sow”, the largest whirlpool in the Northern Hemisphere. According to local folklore, it gets its name from the pig-like sounds it makes. And there are smaller whirlpools – or “piglets”, as they’re known – around the perimeter too.

The trips will also allow you to see the many lighthouses in the area, and to go whale watching. Each one lasts for around two hours. Departure times will be based on the tides and will be confirmed when you book.

12. Kennebunk Boat Tour Adventures, Kennebunk

Kennebunk Boat Tour Adventures, Kennebunk

Looking for speed and adventure on your tour? Look no further than Kennebunk Boat Tour Adventures. Their RIB boat will get you to locations fast, meaning you can stay there longer – and enjoy the wind in your hair!

Trips include tours of the Nubble and Boon Lighthouses. And if you choose the Goat Island Lighthouse option, you’ll dock and get a guided tour inside the lighthouse. There’s also a scenic tour of the coastline and a fantastic whale watching experience.

13. Rugosa Lobster Cruises, Kennebunkport

Rugosa Lobster Cruises, Kennebunkport

Rugosa Lobster Cruises are the only company operating in Kennebunkport to use a traditional Downeast-style lobster boat for their trips. That makes them a great option if you’re looking for an authentic lobstering experience.

They set sail from historic Nonantum Marina. An on-board lobster expert will tell you about the biology of lobsters and the history of Maine’s lobster industry.

Each trip lasts for an hour and a quarter. You can also charter the whole boat in 75-minute chunks. Check the website for real-time availability.

14. Balmy Day Cruises, Boothbay Harbor

Balmy Day Cruises, Boothbay Harbor

Balmy Day Cruises in Boothbay Harbor offer a great range of excursions that cover all interests.

Anglers can enjoy a 2-hour mackerel fishing trip on the Miss Boothbay. It includes a brief tour of the harbor, and all tackle is provided.

Photographers can opt for the sunrise trip, hosted by a professional photographer. This 2-hour trip takes in lighthouses in the golden hour when the light is perfect for great shots.

There are sailing trips, sightseeing trips, lighthouse trips, and trips to see spectacular windjammers sailing into the harbor. You can also take a boat to explore Moneghan Island.

15. Schooner Olad & Cutter Owl, Camden

Schooner Olad & Cutter Owl, Camden

If you want to experience Maine aboard a truly beautiful vessel, Camden has plenty to offer. Olad is a classic sailing schooner built in 1927, and will seat 22 passengers. The cutter Owl, built in 1941, provides a more intimate experience for up to six people.

Both sail every day, and there are a range of different options to choose from, from two hours to a full day.

With notice, the Owl can take your party to Stontington for an overnight stay at a beautiful inn. Or choose Vinalhaven for dinner and a stay in Nebo Lodge. Or how about a tent at Warren Island State Park, together with a lobster-bake? Any would be the perfect choice for a romantic evening.

16. Sea Princess Scenic Nature Cruises, Northeast Harbor

Sea Princess Scenic Nature Cruises, Northeast Harbor

Sea Princess Scenic Nature Cruises run a range of professionally narrated excursions from Northeast Harbor. They’re a great option if you’re looking for a more comfortable trip, keeping to calm waters.

Morning and afternoon cruises of the Arcadia National Park take in the Great Harbor of Mount Desert, Isleford’s fishing community and Somes Sound Fjord. There’s a late afternoon cruise to see seals at East Bunker Ledge. And a 90-minute sunset cruise takes in the views of Somes Sound.

It’s also possible to charter the Sea Princess for your own bespoke trip.

17. Bar Harbor Island Cruises, Bass Harbor

Bar Harbor Island Cruises, Bass Harbor

Bar Harbor Island Cruises operate out of Bass Harbor. Most of their trips take place on the 40-foot R.L. Gott, a small and friendly boat that holds up to 49 passengers. They also have a 23-foot Parker, the Fifinella, that can be chartered for your own fishing or sightseeing trip.

Trips take in both wildlife and scenery, and some include hauling lobster pots too. You can head out for a couple of hours, or charter the Fifinella for a full eight-hour day.

18. Rocky Bottom Fisheries, Portland

Rocky Bottom Fisheries, Portland

Rocky Bottom Fisheries offer a whole range of tours from Portland.

Take in lighthouses, private beaches, islands and wildlife. You can also take part in a lobster demonstration, helping to haul lobster pots and learning about the industry. And you’re welcome to bring your own cooler.

There’s a sunset cruise with music, where you can bring your own bottle too. Book in advance and you can add in a lobster roll to the package.

19. Schooner Appledore II, Camden

Schooner Appledore II, Camden

Enjoy the elegance of a cruise on a tall ship with Schooner Appledore II, based out of Camden. You’ll see wildlife like porpoises, seals, bald eagles and ospreys.

Day and sunset sails are available. And from November to May, the boat can be chartered privately too.

Departure times vary by season. Choose an evening sail, and there’s a discounted price for children up to 12 years old. Daytime sails are free for under 5s, with a discount for children up to 11 years.

20. Sail Portland Maine, Portland

Sail Portland Maine, Portland

Sail Portland Maine offer daytime and sunset cruises by either sailboat or motorboat. The sailboat carries a maximum of six passengers, while the motorboat will carry up to 15. The smaller capacity makes for a friendly and intimate experience. Just book in advance to secure your place.

Each trip lasts for two hours, and you can bring your own bottle on either boat . Enjoy a drink while viewing seals, lighthouses and historic forts around Casco Bay.

21. Schooner Mary Day, Camden

Schooner Mary Day, Camden

For a chance to help crew a boat yourself, check out the windjammer Mary Day.

Sailing out of Camden, this beautiful schooner offers longer trips. The shortest is a two day, one night excursion, ideal for those new to windjamming. The longest is six days. In July, you can even be part of the crew for Maine’s Great Schooner Race. The Mary Day has won it several times!

With extras like lobster picnics, guided lighthouse tours and photography tutoring, these boat tours are very special occasions.

Time to Book a Trip!

That brings us to the end of our look at 21 of the best boat tours in Maine. Whether you want to relax with a professionally narrated excursion, or get hands-on hauling lobster pots, there’s loads to choose from.

Whatever floats your boat, we hope we’ve inspired you to book your perfect trip!

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Booking for 2024 now available! Trips begin in June

Island Cruises

ISLAND CRUISES

Booking now available for 2024 season, bar harbor area boat tours, sailing and fishing charters, trips depart from bass harbor, maine.

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Escape the Bar Harbor crowds! We are located in beautiful Bass Harbor, just 30 minutes from Bar Harbor in Acadia National Park. Join us for a public nature cruise or private boat charter to enjoy fishing, sailing, or sightseeing! 

Public Cruises

  • Info Up to 49 people
  • User All ages
  • Hour Glass 2 hours

Nature Cruise

On this 2 hour tour, you will learn about Maine’s fishing industry, see wildlife, haul a few lobster traps, and enjoy stunning views of Acadia National Park. We cruise past Bass Harbor Head Lighthouse and experience the outer islands of Blue Hill Bay, where you’ll see seals, nesting birds, and more. This nature cruise of Blue Hill Bay and Bass Harbor is one you won’t forget!

Private Charters

  • Info Up to 6 people
  • Hour Glass 2 - 6 hours

Private Fishing Charter

Book a private fishing charter to experience a comfortable day on the water exploring the beauty of Acadia National Park. Our local captains are avid fisherman and know all the best spots; we will create the perfect trip for you.

Private Sightseeing Charter

Our private sightseeing charter allows you to enjoy the beauty of Acadia National Park from the water! View lighthouses, Cadillac Mountain, and wildlife such as seals, eagles, porpoises, & more. Our local captains will help you customize your trip for a wonderful day on the water.  Visit an offshore island for a picnic, hike or dockside dining (4hrs min).

  • June - Sept
  • Hour Glass 2-4 Hours

Private Sailboat Charter

Experience one of the finest sailing destinations on planet earth aboard our beautiful 36’ sailboat charter, Motu Iti . Enjoy the fresh breeze and natural beauty sailing in Blue Hill Bay in Acadia National Park.

BAR HARBOR AND ACADIA AREA BOAT TOURS FROM SCENIC BASS HARBOR, MAINE

Island Cruises offers a leisurely, interactive introduction to the outer islands, wildlife, and history of the Bar Harbor and Acadia area. Spectacular wildlife abounds—from sunbathing seals to majestic osprey and eagles, all observable in their natural habitats. It’s no wonder that the Audubon Society, Nature Conservancy, and Maine Coast Heritage Trust have all made such strong commitments to Blue Hill Bay.

A quiet and relaxing alternative to other Bar Harbor boat tours, Island Cruises is based out of Bass Harbor. We have been family-owned and operated for 30 years. Our primary vessel, the 40-foot R.L. Gott, is a lobster-style passenger boat that carries a small and friendly crowd of no more than 49 passengers.

We’re the perfect venue to see seals, porpoises, herons, osprey, eagles, and other wildlife up close and personal, and haul a lobster trap or two—all while experiencing beautiful scenery and learning the lore of Bass Harbor and Maine’s rich fishing history from local captain Eli Strauss. Whether you enjoy wildlife or just peaceful scenery, Island Cruises has a great trip for you. Step aboard one of our boats for an experience you’ll never forget.

Custom Charters

If you want your own private boat trip you can customize a sail or power boat charter for up to 6 people.  The ultimate way to experience the Acadia coast and create a unique memory of Maine.  Join us on Fifinella our 2320 Parker or Monterey our 2520 Parker, for fishing trips, wildlife, lighthouse trips, or an excursion to an island to enjoy trails few get to see.  Take a sail on Motu Iti and enjoy the fresh ocean breezes and natural beauty of the Maine coast.

BASS HARBOR: THE "QUIET SIDE" OF MOUNT DESERT ISLAND

Escape the crowds of Bar Harbor, Ocean Drive and Cadillac and head to the “quiet side” of Mount Desert Island for a boat tour or charter with Island Cruises.

On your way to us from Bar Harbor, drive through historic Somesville and see original white clapboard houses, church, library, museum and mill pond spilling into the harbor. Take in the scenic Echo lake, formed by glaciers and bordered by Acadia National Park’s Beech and Acadia Mountains. Next, make some time for Southwest Harbor, a small village with great restaurants and shops and a long tradition of boat building; the original home of Hinckley, Morris Yachts, and master wooden boat builder Ralph Stanley. You can also visit the Wendell Gilley Museum to see his famous bird carvings and decoys.

When you join us for a tour or charter, prepare to get the best up close views of Bass Harbor Head Lighthouse, seals, eagles, lobster and other Maine wildlife, and real insight into what is so special about the coast of Maine. You won’t regret making your way to Bass Harbor, the classic Maine fishing village we are so fortunate to call home.

CHECK OUT OUR TRIPADVISOR REVIEWS ★★★★★

a sign on the side of a road

Amazing!! Informative on historical, biological, cultural and economical level! Our guide Eli and his wife Robin were wonderful. Eli had so many interesting facts and stories to share and he was well spoken and extremely interesting. Despite the cold temps we all enjoyed it very much. Even without seeing bald eagles, harbor seals, gray seals, porpoises, lobsters and other birds it would have been a great tour.

We took the Afternoon Nature Cruise on the RL Gott. We saw eagles, seals and even saw a dolphin. The captain was extremely knowledgeable about the islands and their history, and it fascinating to see and learn about them, the salmon hatchery, and lobster fishing. It was also really cool to see him pull in a lobster trap and learn about the lobsters and crabs inside. I would highly recommend this affordable 2 hour cruise!!

The two hour afternoon nature cruise was very enjoyable. Capt. Eli is very knowledgeable about the history of the islands in the Gulf of Maine, and provided details of the people and marine life that live(d) on or around the islands. We saw seals, eagles, porpoises, a salmon farm and a cormorant rookery. Capt. Eli also retrieved a lobster trap to explain how lobsters are caught and measured. A worthwhile experience!

Capt. Eli and first mate Jill were great hosts for our trip. Eli is very knowledgable about the islands and gets the boat real close to the rocks so you can see a light house plus various wild life like seals, porpoises, and on our trip we even saw a bald eagle. The trip included a stop for lunch at the town of Frenchboro on the Island of Long Island. Its a great little fishing village. On the way back Eli hawls up a lobster trap and talks about the lobstering industry in Maine. The entire trip is awesome and well worth it!

sailboat tours maine

The Five Best Guided Tours in and Around Portland, Maine

T he beautiful port city of Portland, Maine has plenty to explore along the water and its other neighborhoods. However some of the best adventures we had in Portland were part of guided tours. This is simply because we do not have our own boat, do not know the in and outs of every part of the historical neighborhoods, or we simply cannot drive while tasting the local breweries.

We have compiled this list of our top five favorite tours that run in and around Portland. Some of these tours only run seasonally during the warmer months, while others require advance reservations. So plan your trip to Portland accordingly, but most importantly enjoy this fun and friendly city!

Portland Discovery Land & Sea Tours

Climb aboard the trolley for a historic tour of Portland with Portland Discovery. Enjoy some of the iconic spots including the Henry Wadsworth Longfellow house and the Victoria Mansion along with some hidden gems of Portland.

This is the perfect tour to bring you to the iconic Portland Head Light lighthouse with plenty of time to walk around and photograph the area. The hour and forty five minute trolley tour includes a 30 minute stop at Portland Head Light. Tickets are $28 per adult and the tours run seasonally from the end of April to the end of October.

Maine Brew Bus

Hop aboard the lime green Brew Bus for a guided tour of several of the best craft breweries in the region. The breweries range from the well established to brand new, with a rotating schedule of nearly 30 locations and over a dozen different tour options. Beyond the tastings, you also get a behind the scene look at the brewing process and a range of brewery setups.

Have no fear about getting around and let everyone in your group try some local libations with the Maine Brew Bus. It is not just about the local brews, they also offer wine and spirits tours or a combination of all three. Tours range from $65 to $85 per person with a variety of tours running each day, so check the schedule to find the one that matches your interest.

Sunset Schooner Sail

Hop aboard a historic schooner for a romantic sail through Casco Bay with Portland Schooner Company . Enjoy a leisurely afternoon on the boat, set sail for where the wind will take it. While they try to sail towards the waters off of Portland Head Light, the wind direction does not always allow. Either way you will get to see the beautiful coast of Maine and its diverse wildlife.

The schooners sail daily from May through October with multiple departures throughout the day, but we highly recommend the latest in the day for an enjoyable sunset sailing. The two hour sailing costs $45 per adult and you can bring along your own food and drinks if you would like to enjoy a picnic at sea.

Lucky Catch Lobster Cruises

No trip to Portland or Maine in general would be complete without the chance to catch some live lobsters. With Lucky Catch Cruises the tour is not just about picking up the lobster traps. You can also refill the fish bait bags, learn the history and laws regarding lobstering of Maine and about the life of a lobster/fisherman. Did you know that to keep a caught lobster in Maine it has certain size requirements and cannot be too big or too small?

The lobster cruises enjoy a scenic ride along the way, with route options including White Head Passage, a chance to spot seals, and even a glimpse of Portland Headlight. Tickets for the 90 minute lobster tour are $35 per adult with the opportunity for you to purchase some fresh caught lobster at the end of the tour.

Maine Duck Tours

One if by land, two if by sea, or both if by Maine Duck Tours ! Enjoy an exciting tour on land through the historic district of Portland before driving straight into the water for a look at the waterfront from the waters of Casco Bay. This hour long tour is perfect for a glimpse at the city both on dry land and water. Tickets are $31 per adult with advance reservation recommended.

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The beautiful port city of Portland, Maine has plenty to explore along the water and its other neighborhoods. However some of the best adventures we had in Portland were part of guided tours. This is simply because we do not have our own boat, do not know the in and outs of every part of …

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COMMENTS

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  23. Island Cruises

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  25. In Memoriam

    (2008) and performed in both the first (2005) and second (2009) national tours of Wicked, playing the replacement Fiyero in the second tour. In more recent years, Peluso enjoyed great success in London's West End, starring in Miss Saigon (2015), Show Boat (2016), The Woman in White (2017), and in the UK tour of Funny Girl (2017).