sailboat tour boston

BOSTON sailing Tours

Private sailing charters for up to 6 guests around boston harbor & islands., boston sail tours, sailing charters for up to 6 guests around boston harbor & islands.

Boston Sailing Tours offers private sailboat charters in the Boston Harbor and the Boston Harbor islands.

We offer relaxing private tours of the inner harbor where you can enjoy your favorite food and wine for your special occasion and also extended sailing tours and exploration of the islands that are only accessible by private boats.

Consider booking one of ours private sailing charter for an unforgettable experience.

With a variety of options available, you can relax and take in the stunning views of the city skyline or go on a sailing adventure to the harbor islands where you will see deer, wild life, and enjoy magnificent beaches with no one around.

We are the only sailing tour operator who can take you to Lovells, Grape, and Bumpkin Islands and allow you to explore these islands as part as your charter.

The charter season for Boston Sailing Tours runs from spring to fall allowing you to take advantage of the pleasant weather and optimal sailing conditions during that time. You can directly book your private adventure with Boston Sailing Tours or call 617-279-3981 for information and availability.

This unique sailing experience promises to provide you and your guests with a memorable and breathtaking journey through the beauty of Boston Harbor and its islands.

We offer relaxing private tours of the inner harbor where you can enjoy your favorite food and wine for your special occasion and also extended sailing tours and exploration oaf the islands that are only accessible by private boats.

2 Hour Harbor Sail From $545

Spectacular views of the Boston Harbor skyline

Full Day Sailing & Island Experience From $ 950.00

Authentic Sailing Experience & Island Exploration

Departing Location

In the heart of the Seaport District

1 Courthouse Way, Boston, MA 02210

Mailing Address:

28 Constitution Road

Charlestown, MA. 02129

617-279-3981

[email protected]

Departing Location:

© ALL RIGHT RESERVED BOSTON SAIL TOURS OWNED & OPERATED BY CGN MARINE LLC. | SITE DESIGN BY  NXTMEDIA

Classic Sail Boston

Welcome to Classic Sail

Private Charters in Boston Harbor

Classic Sailing

See Boston from a 45' Classic Wooden Sailboat

Sail or Motor

Classic Boston Style 2 Ways

Fun For Any Occasion

Special Occasions, family outings, parties with friends

Libations and Food Welcome

BYOB Encouraged

Classic Sail Charter Options

2 hour private charter.

Sail with us around the inner harbor to see the BEST of Boston including Seaport, Southie, Castle Island, Spectacle Island, Eastie, Charlestown, and The North End. Let us regale you with the history of these places, or just listen to some music and enjoy a leisurely sail around the harbor. We specialize in hosting private events; birthdays, anniversaries, proposals… we do it all. Complimentary soda and water are always on board and you’re welcome to BYOB anything else you wish! Convenient pick up location in Boston’s Seaport District, with custom pick up/drop off locations throughout Boston Harbor upon request.

4 Hour Half Day Private Charter

Sail out to the Boston Harbor Islands on this extended version of our tour. Enjoy sailing around some of the further islands before returning to the inner harbor for the rest of your tour. Or, design your own half day adventure, just tell our captain what you would like to do!

Full Day Private Charter

Spend your day sailing around and exploring all that the inner and outer harbor have to offer.  You are welcome to bring snacks, lunch, libations or anything else you like aboard to enjoy during your day on the water with us. You can explore the islands and lighthouses up close, we can throw the anchor and take a dip, island hop, and get the extended tour of the area. It’s your boat for the day and we’ll make sure its unforgettable! Book Now

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City Cruises – Boston

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Frequently Asked Questions

What are the top cruises in boston.

• Boston Whale Watching Cruise
• Boston Sunset Sightseeing Cruises
• Boston Speedboat Tours
• Provincetown Ferry

More about the best boat tours in Boston

Boston cruises along the skyline offer one of the best views of the city. There are also many great options for sightseeing cruises that will take you past some of Boston’s most famous landmarks. If you’re looking for a more unique experience, there are also a number of themed cruises available that focus on everything from local history to Halloween fun. Whatever you’re looking for, there’s sure to be a boat tour in Boston that’s perfect for you. Including dining cruises! Who doesn’t want to enjoy brunch on dinner on the water? You’ll also get to enjoy live entertainment and dancing as you sail around Boston Harbor.

Are private boat charters in Boston available?

• Boston Boat Charters
• Boston Party Cruises
• Boston Corporate Events
• Boston Wedding Cruises

Which landmarks and famous sights can you see on a Boston cruise?

On a Boston Harbor cruise, you will experience firsthand the sites that made Boston one of America’s first great cities. Iconic landmarks like the USS Constitution Museum, the Bunker Hill Monument, and Fenway Park are all within view. You will also get unparalleled views of historic sites like Harvard University, Boston Common, and Quincy Market. Whether you are looking for a romantic evening cruise or a family-friendly tour, there is a Boston Harbor cruise that is perfect for you. Enjoy the sights and sounds of this beautiful city from the comfort of a boat and make some amazing memories along the way.

Water & Boat Attractions in Boston

Premier Dinner Cruise on Odyssey | Signature Dinner Cruise on Spirit of Boston | Premier Brunch Cruise | Premier Lunch Cruise | Provincetown Fast Ferry | Boston Harbor Islands Ferry | Salem Ferry | Boston Water Taxi | Ferry Multi-Ride Passes | New England Aquarium Whale Watch Cruise | Sunset Sightseeing Cruise | CODZILLA Thrill-boat Ride | Historic Harbor Cruise | Peddocks Island

Things to do near Boston

Things to do in Washington DC | Things to do in Baltimore | Things to do in Jersey City | Things to do in New York | Things to do in Weehawken | Things to do in Niagara Falls | Things to do in Philadelphia | Things to do in Toronto | Things to do in Chicago | Things to do in San Francisco

Recommended for Boston

Boston Tea Party Ships and Museum | Freedom Trail with North End Neighborhood Walk | Ultimate Boston Food Tour: Freedom Trail & North End | VIP Freedom Trail Tour: Revolutionary Church Steeple & Paul Revere’s Home

Trending Attractions

New England Aquarium Whale Watch Cruise | Official NYC Downtown Experience – Statue of Liberty, 9/11 Memorial & Museum, One World Observatory | Washington DC: Big Bus – Classic Tour | Monuments Tour From The Wharf | Mount Vernon from DC | Monuments Sightseeing Tour From Alexandria and Georgetown | Chicago Seadog Lakefront Speedboat Tour | Toronto Sightseeing Harbour Tour | Chicago Seadog Lakefront Speedboat Tour | Depths & Discovery of the 1000 Islands Cruise | CODZILLA Thrill-boat Ride | Chicago Seadog River & Lake Architectural Tour | 1000 Islands Boldt Castle Stopover Cruise | Voyage to Niagara Falls Boat Tour | New Jersey Ellis Island Hard Hat Tour | New Jersey Statue of Liberty Pedestal Reserve

Holiday Experiences in Boston

Premier Dinner Cruise on Odyssey | New Year’s Eve Premier Dinner Cruise |  Boston Brunch with Santa Cruise |  Boston’s Valentine’s Premier Dinner Cruise

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THE 10 BEST Boston Boat Tours

Boat tours in boston.

• Fishing Charters & Tours
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• Up to 1 hour
• 1 to 4 hours
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• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
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• Classic Harbor Line Boston MA Day Tours
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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.

1. Boston Harbor Sunset Cruise

2. Boston Historic Sightseeing Harbor Cruise with Up-Close View of USS Constitution

3. Boston Harbor Sightseeing Cruise

4. Boston Signature Dinner Cruise

5. Boston Harbor Brunch Cruise

6. Sunset Cruise

7. Boston Harbor Sunset Sail Tour

8. Boston Premier Dinner Cruise on Odyssey

9. Sightseeing Day Sail around Boston Harbor

10. Boston Signature Lunch Cruise

11. Boston Premier Brunch Cruise on Odyssey

12. Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

13. 90-Minute Boston Harbor Sunset Sightseeing Cruise

14. Boston Codzilla High-Speed Thrill Boat Ride

15. Private Trinacria Fishing and Cruising Boston

16. Dog Day of Summer Harbor Cruise in Boston

17. Lighthouses and Tales of Boston Harbor

18. Boston Mother's Day Premier Dinner Cruise

19. Boston Alive after Five Cruise

20. Holiday Sunset Cruise in Boston Harbor

21. Boston Holiday Cocoa Cruise

What travelers are saying.

• Boston Harbor Sunset Cruise
• Boston Historic Sightseeing Harbor Cruise with Up-Close View of USS Constitution
• Sunset Cruise
• Boston Harbor Sightseeing Cruise
• Private Trinacria Fishing and Cruising Boston
• Night Rider Private Charters of Boston
• ForeverVacation Boston
• Boston's Best Tours
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• Captain Walt Shoemaker
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• Classic Sail Boston
• Massachusetts Bay Lines
• Come Sail Away Now Charters

• Fan Favorite Cruise!

Boston Harbor Sunset Cruise on a Tall Ship

Quick Details

• Hour Glass Duration: 1.5-2 Hours
• Clock Time of Day: Evening

Enjoy a Boston Sunset Cruise Aboard a Boston Tall Ship!

Sunset sail in boston harbor.

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Central Wharf and raise the sails, then it’s time to just chill out and relax. With a breeze guiding us through the harbor, you have a great vantage point to watch the sun go down behind the city and bathe it in incredible colors as the lights of Boston’s skyline begin to sparkle in the twilight. This is a tall ship sunset cruise to remember.

The Liberty Star schooner has deck space for up to 35 passengers and sails from 6:30-8pm.

Grab a drink from our bar — our special is the sailor’s favorite, the Dark ‘n’ Stormy, made with Gosling’s dark rum, ginger beer, and a twist of lime! Non-alcoholic beverages are also available. A Boston Harbor sunset cruise is a great way to end a busy day or to start out a fantastic night.

Liberty Fleet has Health & Safety procedures in place and is ready to welcome our guests onboard for a safe adventure offering plenty of fresh air, sunshine, and space onboard.  We sail according to the strict safety guidelines of the City of Boston. Tickets and drink vouchers can be bought online ahead of your cruise if you would like contactless purchases so please take a look at our website or purchase your tickets at the booth when a crew member is present.

What to Bring

Beverages are available for purchase on board for you to enjoy during your sail. A cash bar (or buy drink vouchers online before your sunset cruise) is also available. As it is usually cooler on the water, we recommend bringing an extra layer such as a light pullover or jacket. Feel free to bring a bagged lunch and snacks but coolers are not permitted.

Related Cruises

• Evening Cocktail Cruises
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Cocktails, Rum, & City Lights Cruise (21+)

Join a Saturday evenings for our after-hours Cocktails, Rum, & City Lights Cruise.  NEW PRICE & GROUP DISCOUNT FOR PARTIES OF 4!

• PLEASE CHECK BACK FOR 2024 SCHEDULE
• Hour Glass 1.5-2 Hours

Boston Harbor Day Sailing Cruises

Come aboard for a day sail in Boston Harbor on one of our classic schooners! Sailing is a great, family-friendly way to see Boston from a new viewpoint.

• HARBOR HISTORY CRUISE ON A TALL SHIP!
• Hour Glass 2 Hours

"A Sail Through Time" with Boston By Foot

“A SAIL THROUGH TIME”  Learn about Boston’s history while aboard a classic schooner. The cruise follows the paths of ships like the Flying Cloud, Astrea, and Columbia, exploring how their voyages shaped Boston and helped industrialize the country.  Tourguide / Onboard Docent from Boston By Foot.

Local News | USS Truxtun stops in Boston for weekend visit

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It’s hard to miss the USS Truxtun, an Arleigh Burke-class guided-missile destroyer now tied up at Black Falcon Terminal for a weekend visit.

The public is invited to tour the Truxtun from 9 a.m. to 2 p.m. Saturday and Sunday, immersing themselves in its maritime history and heritage. She was named for Commodore Thomas Truxtun, one of the first six Navy commanders appointed by George Washington, and was an active participant in the Mexican–American War.

Boston, MA - Joyce DiCicco hugs her son, ENS Andres Loder, after he brought the destroyer USS Truxton to the dock at Black Falcon terminal. Looking on is Loder’s aunt, Joanne Danilchuk.(Nancy Lane/Boston Herald)

Boston, MA - CDR Chance Smith, Commanding Officer of the destroyer USS Truxton speaks after the ship docked at Black Falcon terminal. (Nancy Lane/Boston Herald)

Boston, MA - Joanne Danilchuk, whose nephew ENS Andrew Loder was bringing the ship in, takes a photo as the destroyer USS Truxton docks at Black Falcon terminal. (Nancy Lane/Boston Herald)

Boston, MA - Marjorie Loder, Joyce DiCicco, Joanne and David Danilchuk, whose family member ENS Andrew Loder was bringing the ship in, watch as the destroyer USS Truxton docks at Black Falcon terminal. (Nancy Lane/Boston Herald)

Boston, MA - ENS Andrew Loder, hugs his wife, Majorie, as his mother and aunt look on after he brought the destroyer USS Truxton into the dock at Black Falcon terminal. (Nancy Lane/Boston Herald)

Boston, MA - Joyce DiCicco hugs her son, ENS Andrew Loder, after he brought the destroyer USS Truxton to the dock at Black Falcon terminal. (Nancy Lane/Boston Herald)

Boston, MA - Sailors line the ship as the destroyer USS Truxton docks at Black Falcon terminal. (Nancy Lane/Boston Herald)

The destroyer USS Truxton docks at Black Falcon terminal. (Nancy Lane/Boston Herald)

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The Schooner Adirondack III

April 4, 2016 by [email protected]

Adirondack III was designed and constructed specifically for carrying passengers comfortably, which is uncommon for historic schooners. Due to the modern and innovative design of Adirondack III , guests will have room to sit and move around the boat.

Adirondack III measures 80 feet in length overall with a 16-foot beam. Her lines are modeled after 1890s style pilot schooners. Adirondack III is long and lean with a spoon bow, which helps her ply through the waters more effortlessly than the average schooner. An all-wooden vessel with a white glass overlay hull, Adirondack III is quite easy to pick out amongst her fellow schooners with her smooth clean lines. When you step aboard Adirondack III you’ll notice her clean teak decks and brilliantly varnished mahogany rails. When your focus takes to the sky above you, you will find two towering Douglas Fir masts and nearly 2,000 square feet of sail stretching to the sky. Adirondack III is sure to amaze you and your guests with her majestic beauty. Whether you are out on one of our sightseeing cruises or you want to have a romantic Boston sunset sail, Adirondack III will be sure to impress! Sail Boston Harbor aboard this beautiful schooner and take in the sights of Boston in style.

Adirondack III is a U.S. Coast Guard certified vessel sailing with U.S. Coast Guard licensed captains and only the most experienced and hospitable crew. She is equipped with an abundance of life jackets, two well-appointed bathrooms, blankets for cool evenings, and beverages on all trips.

Posted in | Comments Off on The Schooner Adirondack III

“ The sail was wonderful! Perfect day! Perfect weather! Captain and his crew were terrific. We are highly recommending it to all our friends. Would consider arranging a private party get together to sail in the future. Thank you.”

“Great experience! We were blessed with a fabulous evening for our sunset cruise, but the boat and the crew were terrific as well. The Adirondack III is the perfect size - small enough for an intimate experience and large enough to feel safe and comfortable .”

“My husband and I had a great time. It was something out of the everyday. The planes were flying directly over us, the crew was awesome and the scenery was breath taking. Would definitely recommend it for a romantic night out .”

“ The cruise was fantastic and the crew was extremely friendly . Whether you're visiting Boston for the first time, or you have lived here for years, you'll see the city from a beautiful perspective in a very enjoyable way. I really recommend this cruise experience.”

“What an amazing evening on the water! My Mom and I took family from out of town on this boat trip. We had been once before and they kindly remembered us and were happy to see us return. I can't say enough about the staff. They are genuine, friendly and make you feel right at home. And the boat is beautiful. It was a perfect night for being on the water. Our family LOVED it! We will be back again! ”

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Sail out from Rowes Wharf and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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