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Top 13 Chesapeake Bay Cruising Destinations

Aug 26, 2020

One of the big advantages of owning an inflatable boat is the ability to travel where you want, whenever you want, to enjoy a day of sailing. If you're a Maryland, Virginia, or D.C. resident, you have access to one the world's best cruising destinations, the Chesapeake Bay.

From fishing and national parks to delicious food like crabs and oysters, the Chesapeake Bay has a lot to offer. Covering over 4,000 square miles, there is plenty to explore. Below you'll find the top 13 Chesapeake Bay cruising destinations.

1. St. Michaels

Located on Maryland's Eastern Shore, St. Michael's, Maryland has plenty to offer despite being home to a little over 1,000 people. Home to the Chesapeake Bay Maritime Museum , several art galleries, restaurants, and other historic landmarks, St. Michaels is also a prime cruising destination. Located on the water, St. Michael's is a perfect place to access the Chesapeake and it offers up some wonderful views.

2. Galesville

Located on the western shore of the bay, Galesville is a small town that sits along the West River. A steamship line in Galesville used to connect Annapolis and Baltimore, and the town was once home to many Chesapeake Bay Watermen. It is now a hot spot for pleasure boating and home of the West River Sailing Club and Hartge Yacht Harbor

Located along the Tred Avon and Choptank Rivers, Oxford, Maryland is home to the Oxford-Bellevue Ferry, the Tred Avon Yacht Club, and the Oxford Museum . The ferry is believed to be the oldest privately owned ferry, with service dating back to 1836. In addition to its local attractions, Oxford access to the Tred Avon and Choptank makes it a great cruising destination for sailors and boaters alike.

Located 40 minutes south of Annapolis, Deale, MD provides many scenic views of the Chesapeake, making it a popular destination with boaters. Home to waterfront bars and open-air crab houses, Deale is perfect for anyone looking to hit the open water for the day and then enjoy a good meal afterwards.

5. Solomons Island

Located at the mouth of the Patuxent River, Solomons Island was the home of many 19th century shipyards that supported the local fishing economy. Today, Solomons Island is home to many marinas, seafood restaurants, the Calvert Marine Museum , and the Annmarie Sculpture Garden & Arts Center . Its position along the waterfront make it a prime destination for cruising.

6. Rock Hall 

The jewel of the Upper Eastern Shore, Rock Hall, MD is a picturesque cruising destination. Serving as the hub for Kent County's maritime industry, Rock Hall is home to the Rock Hall Yacht Club, over a dozen marinas, various charters, boat rentals, and more! A day of cruising in Rock Hall will give you access to beautiful scenery and plenty of open water to explore.

7. Chestertown

Located along the Chester River, Chestertown was once one of the six Royal Ports of Entry and considered Maryland's second leading port. Today, Chestertown is home to Washington College, a number or restaurants and historic attractions. Offering a wide range of scenic and historic sailing views, Chestertown is a perfect location for day cruising.

8. Kent Island

The largest island in the Chesapeake, Kent Island, is nestled between Annapolis and the Eastern Shore of Maryland. The Cross Island and South Island trails provide plenty of outdoor activities across the island. For those looking to cruise the open waters, Kent Island offers unique access to the Eastern Bay, Chester River, and the heart of the Chesapeake Bay itself.

9. The Wye River

With easy access to fishing and crabbing destinations, the Wye River is a favorite cruising destination for many. Add in the Wye Island Natural Resource Management Area, and you have a perfect destination for cruising and exploring the outdoors.

10. Baltimore

Baltimore's Historic Inner Harbor is the mouth of the Patapsco River. With access to a number of marinas, the Inner Harbor is a great launch point for day cruising. Enjoy views of historic Federal Hill and Fort McHenry in the Harbor, and as the Patapsco opens up into the bay, you'll find additional outdoor destinations such as North Point State Park and Fort Smallwood Park.

11. Annapolis

Sometimes referred to as the Sailing Capital of the U.S., Annapolis is home to various boat shows, the Naval Academy, and the National Sailing Hall of Fame. Its position along the South River, Severn River, and the Chesapeake Bay make it a great launch point for cruising.

12. Washington DC

The beautiful Potomac River runs directly through the Nation's Capital, making Washington, D.C. a prime destination for sailors. With access to historic views in the heart of D.C. to a variety of parks and outdoor destinations, D.C. is a great place to spend a day out on the water.

13. Havre de Grace

Sitting at the mouth of the Susquehanna River and the head of the Chesapeake, Havre de Grace is uniquely positioned to several state parks and scenic views including Elk Neck State Park and Susquehanna State Park. With easy access to the water and the outdoors, Havre de Grace is a worthwhile destination for anyone looking to explore the bay.

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We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md, we sail april 19,2024 to nov 3, 2024, clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

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2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

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St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

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Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

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Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

Chesapeake Windsail Cruises

Sailing on the bay with Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 ½ hour cruise on the Chesapeake Bay.

Chesapeake Windsail Cruises sails out of the beautiful Rod 'n' Reel Resort located in the bay-side town of Chesapeake Beach, Maryland, where you can dine before or after your cruise at the Rod ‘n’ Reel restaurant.

We hope you enjoy browsing our website and find a lot of useful information for your cruise or walking tour .

We hope you enjoy browsing our website and find a lot of useful information for your cruise.

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Chesapeake Sail Club

Sail the chesapeake bay for the 2024 season, boad creek, deltaville, virginia.

Our home port, Broad Creek, at the mouth of the Rappahannock River, means great destinations on the river and bay are within an easy morning or afternoon sail.

Explore the numerous deep water creeks off the Rappahannock – drop your anchor or berth at the available facilities and explore local villages. Favorites include Urbanna, Topping and Irvington.

Set course for a secluded creek and enjoy the natural beauty and wildlife that only the Chesapeake Bay area can offer, favorites include the Corrotoman and Antipoison.

Sailing Chesapeake Bay from Broad Creek, heading either north or south there are numerous bays, rivers and waterfront towns to visit. Favorites include Fleet’s and Little Bays, Great Wicomoco River area and Mobjack Bay.

Sailing east, across the bay, to the eastern shore, you will find quaint and welcoming towns such as Onancock and Cape Charles.

Solomons, MD and Portsmouth/Norfolk, VA are within a few days of sailing from our Rappahannock home port, when your schedule allows.

What Members are Saying

My daughter and I had a great day sailing yesterday. The friends we took with us had a great day as well. Read more

The CSC Fleet – Our Sailing Yachts

With the start of the 2023 sailing season, club members can sail either Bianca , a Tartan 34 keel/centerboard sloop or Ula, a Freedom 32 – your choice each time you reserve sailing time. Both yachts are well equipped, comfortable cruisers.

Chesapeake Bay Sailing Cruises Sharp St. Pier -  Rock Hall, Md 410-708-1803 - [email protected]   90 Minutes - Up to SIX Guests $35 per person Serving Rock Hall for 25 Years!   Trip Advisor #1 "Thing to do" in Rock Hall Day Sails - Sunset Cruises - Privates - Weddings - Special Occasions - Lessons and Instruction 

Blue Crab Chesapeake Charters Rock Hall, Md Sailing Charters

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CELEBRATING 25 YEARS IN ROCK HALL Voted! - 2022 Best of the Eastern Shore - Best Tour Boat!! Voted 2023 - Best of Eastern Shore - Best Charter Company 

            Click HERE to view our video from our 2019 Caribbean cruise, "Island Odyssey - A Destiny Fulfilled

AN AWARD-WINNING EXPERIENCE!

Providing sailing cruises 25 years  in Rock Hall, Md, Blue Crab Charters provides an award winning experience that you won't want to miss! Take the helm or just relax as you set sail from Rock Hall Harbor into the open Chesapeake Bay or the scenic Swan Creek. Blue Crab Chesapeake Charters is home to Rock Hall's Original Sunset Cruise and will surely top off any visit to Maryland's Eastern Shore.  ​

Your hosts are full-time residents of Rock Hall and are ready to sail 7 days a week up to fives times daily, from April through October. Our sailing vessel, "Island Girl" is a 43 foot Morgan center cockpit sailboat with lots of deck space and a full cockpit enclosure for your comfort.  You will find us conveniently located at the Sharp Street Pier at Waterman's Crab House.  Reservations are required and can be made by phone or email.

Let the wind do the work! The Fuel is FREE!  The experience is priceless! And the memories last a lifetime! Captain Mark and First Mate Suzanne are standing by to take your call or email! See you in Rock Hall!

• St. Michaels On The Bay
• The H.M. Krentz
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• Skipjack History

“ Relaxing, educational and unforgettable! ”

Enjoy a sailing tour on Chesapeake Bay waters aboard this rare skipjack.

The H.M. Krentz is an authentic working skipjack. One of the newer vessels to be built for the rigors of Maryland’s wintertime commercial oyster dredging fishery. Launched in 1955 in Harry Hogan, Va., by the Krentz Shipyard for Capt....

After choosing to pursue an education by experience, Capt. Ed participated in the pilot internship programs of Dynamy in Worcester, Mass., and worked with the Hurricane Island Outward Bound School and the Apprecticeshop in Maine. Then, sailing...

St. Michaels is the center of a unique and magical waterworld on Maryland’s fabled Eastern Shore, about halfway between the Susquehanna source and the Atlantic mouth of the Chesapeake Bay. This diminutive well-preserved vintage port,...

Chesapeake Bay Sailing Tours

Enjoy a relaxing, educational, and unforgettable sailing tour on Chesapeake Bay waters on the historic skipjack H.M. Krentz. We can arrange for catered picnics, cocktails and hor d’oeuvres, or you can bring your own food and beverages. Dress as comfortably and casually as you like.

Advance purchase recommended as t ours often sell out. 

**If you would like a private charter, please call (410) 745-6080 or email: [email protected]

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Sail Chesapeake Bay

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Explore the USA's Largest Estuary and Discover America

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkeling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

So convenient for the locals and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

It All Starts in Annapolis, America's Sailing Capital

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A. Michener's great novel Chesapeake. 

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

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The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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2 Hour Public Sailing Cruises

“My husband and I sailed with you on last Saturday evening’s sunset cruise…we were with our dear friends who were celebrating their 25th anniversary. We all had such a wonderful time! Candidly, I was a bit apprehensive, having never sailed before and not knowing what to expect, but I will definitely be back! We all will. Thanks again, so much, for a wonderful adventure.”

Marieanne H.

“We love sailing on the Woodwind and Woodwind II; It is part of our summer plans every year, especially when family comes from out of town. The crew is always fun and professional and each sailing is a new adventure!”

The Paulsons Urbana, Maryland

Woodwind sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel. Each trip is unique. Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.

On our cruises you will see:

• United States Naval Academy
• Annapolis Harbor
• Chesapeake Bay
• Scenic views of Annapolis skyline
• Severn River

Depending on the wind direction and speed, you may see:

• Chesapeake Bay Bridge (we may even go underneath)
• Thomas Point Lighthouse
• Kent Island
• Regattas competing in the Bay
• Ospreys and other local birds
• Watermen checking their catch

The 74-foot schooner Woodwind and Woodwind II were custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit distinguish her from cargo-carrying work vessels. Our bar is stocked with wine and beer, including a nice selection of local craft beer.

Have a group of up to 16 passengers?

You can get your tickets further in advance and be welcomed aboard first. Click here to learn about our group sailing packages on public cruises.

Weekday sunset sails include the following events or entertainment:

History Mondays

A guided tour exploring the history of the area, the Chesapeake, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Early May – September.

Beer Tasting Tuesdays

Sample while you sail! Each month we feature a different brewery from the Mid-Atlantic Region, and their representative comes aboard and teaches you about beer. 3 samples of beer come with the cruise, and then order full beers from the brews that you enjoyed the most.  Schedule of Breweries.

Wednesday Night Races

Join the crew and race Woodwind vs. Woodwind II every Wednesday night from April 27 through August 31. 100 other sailboats also race in the Wednesday Night Regatta. Wednesday’s are the nights to Party Like A Sailor.

Thursday, Friday, Saturday, and Sunday

There is no specific entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew serve up your favorite beverage as you relax watching the sunset over the city skyline.

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Fully Crewed Sailing Yacht Charters

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Book your private fully crewed luxury sailing charter on a catamaran or monohull in the Chesapeake Bay and Hampton Roads. Perfect for couples or small groups.

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The largest and at most famous estuary in the United States, Chesapeake Bay (or “the Chesapeake”) is truly an extraordinary place. Stretching across six states and the District of Columbia, the Bay watershed never ceases to amaze with its rich history, vital economic importance, and astounding beauty. And the wonders of sailing the Chesapeake Bay could fill a lifetime.

The history, natural beauty and wonderful ecosystem combine to present visitors with endless possibilities, and there’s a new adventure around every corner. However if you only have a limited amount of time to explore, it’s best to get an understanding of what there is on offer before your trip.

The following are a couple of tips for planning your sailing adventure on the bay.

How to Stay (Find Airbnbs & Hotels)

Here is an interactive map of hotels and airbnbs you can book in the Chesapeake area.

Be Realistic

If you try to see everything, it’s likely that you’ll miss a lot. Considering the scale of Chesapeake Bay , you will have to be realistic. It is not somewhere to speed around trying to encompass it all in one visit.

Do it right, and you will enjoy the experience so much more and thereafter, who knows, you may return to continue the adventure.

Remember the Definition of Cruising

To sail about for pleasure in an unhurried or unconcerned fashion, to move leisurely about an area. Let the Bay dictate your pace, stimulate your interest, suggest stops and places to see.

Be flexible in your approach, do plan, but don’t think that the plans cannot be altered once you arrive.

Summers are hot and humid, whereas Spring and Autumn are long, and much more comfortable. Even being on the Bay cannot always provide sufficient respite from the still humidity of the summer months, so be warned.

How to Travel

Cruising can take two forms. You can charter a vessel either bareboat or crewed .

Bareboat – You take charge of the boat yourself and provide the crew, and if you are a competent sailor, then this may heighten the excitement, but it is also less of a vacation and more of an adventure. Don’t forget also the issue of stopovers, are you mooring, docking, or anchoring the boat!

Crewed – the cruiser is manned with a captain and crew, and you can sit back and enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties.

Itinerary Suggestions

There is simply so much, in a sense too much, to see, so it may be a good starting point to pick a more defined area of the Bay and concentrate on that.

Though you’re looking for variety then sailing the Chesapeake area is a natural cruising route for discovery, made for simply hopscotching from one shore to the next, with things to see, visit, experience, taste and indulge all of your senses at once.

Commonly visited areas include Havre de Grace via the Chesapeake & Delaware Canal built in 1829. Many people choose to visit the inner harbour of Baltimore travelling along the Sassafras River with its steep banks and from there to Rock Hall, a sailors town famed for its seafood; travel from St Michaels to Annapolis, known as the sailing capital of the World ; onward to Oxford on the Trent Avon, a sleepy, quaint and picturesque town, or finally on to Washington DC should the mood take you.

You will find yourself with so many options and avenues of adventure, so many that a sense of spontaneity should be a prerequisite. Whilst you slowly absorb the sights, sounds and scenery as you are cruising, you can smile to yourself and be proud that you chose to sail the Chesapeake Bay.

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Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind  Waking Up Wild ; a website dedicated to opening your eyes to the wild & natural world.

Committed to bringing you the best in adventure travel from all around the globe, there is no mountain too high, and no fete too extreme! They haven’t been everywhere, but it’s on their list.

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20 Comments

Great post, loved the pics! I’ll definitely try to go to Chesapeake!, I’m the kind of person who don’t want to miss anything but I’ll follow your advice “If you try to see everything, it’s likely that you’ll miss a lot.” and as you said, maybe I could return a second time and try to see everything. Thanks for the info! Pilar http://www.thelifestylehunter.com

Thanks Pilar! So glad you enjoyed the post :) Yes, definitely recommend to pick a more defined area of the Bay and concentrate on that if it’s your first time visiting – there really is just so much to see and do that it’s better to do a little and enjoy it fully than try to slam out a lot and enjoy it half as much.

Hope you have an amazing time!

At university I had a friend who was always talking about the wonders of Chesapeake Bay and she made it sound like something I really should do. Many years later, I still haven’t, but your post has reminded me how wonderful it sounded.

So glad we could remind you Sarah! Yes, highly recommend a trip – it’s a beautiful bay with so much to see and do :)

Great tips! You’re so right about the weather. I live in DC and the summers are unbearable. Sailing in the fall is the best time. Annapolis is my favorite place on the bay.

Thanks Jessica :) Awesome to hear you’re already familiar with sailing on the Bay :)

I will go for the bareboat one where you have total control. Loved the suggestions and nice pics.

Awesome Gokul! Glad to hear we’ve inspired you to take a trip :) Let us know how you enjoy the Chesapeake

Really good tips. Would love to do this. I would love to lay out and let someone man the boat.

Thanks Holly – yes, jumping on a crewed boat is great if you’re looking to enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties :)

Happy travels!

This is my home! I was so excited to see my beautiful corner of the world featured!

What an incredible place to grow up! Not bad having Chesapeake Bay as your backyard :) Awesome!

Hey Megan, I once got invited on a boat but the trip never ended up going through as the boat needed tons of work and couldn’t get out of the port. This sounds amazing. I’d prefer warm waters in the Caribbean but I imagine seeing this side of the US would be gorgeous as well. Thanks for the post. Cheers, Jack

Hi Jack, thanks for your comment :) Sorry to hear your boat didn’t end up going out on Chesapeake – totally agree that the Caribbean is an incredible spot for sailing too. Very different experience to the Bay but they both make for great sailing :)

Dear Sir, May 22nd, 2018 I have a 27 ft Bayliner sailboat and I would like to sail from Norfolk to Annapolis and back. I have never done this before but it is something that I really want to try. My daughter lives near Annapolis and is close to the water (West River). I feel that I need some bay sailing but I do know how to sail on lakes (Smith Mountain Lake in VA). I am retired and am a good swimmer. I have no idea as to where one would stop for the night and how long it would take and how safe it is to do this. These are my questions and I would like to talk to your group about lessons and feasibility.

Thanks in advance for your time.

Tim Kute 336-413-6126 [email protected]

Hi Tim, thanks for reaching out. We’re a couple who run a personal blog with tips from our adventures, so unfortunately can’t advise you on things like organizing lessons or your level of experience. I would pose your questions to the team at Annapolis Bay Charters who may be able to offer you more insight. Hope they can help :)

http://www.annapolisbaycharters.net

Hi, Sailing is a life fun for those who live for sail like me.I really like the Sailing tips you share with those who live for sail. its help the new sailors in sailing and boost the moral of the experienced sailors. i appreciate your efforts. One thing i like to add is that don’t forget to protect your hands during sailing with premium quality sailing Gloves.

Glad to hear from a fellow sailor! Great tip on remembering to include gloves in your kit :)

Thanks for this. We are thinking of sailing down from Boston to Chesapeake via canal. We have 6-week sabbatical so plenty of time. We would like to avoid the worst of the summer heat/humidity, what would be best time to go in your opinion?

Also, I’ve heard that there are a lot of shallow spots in the bay, we draw 6′, any specific areas to avoid?

Thanks, Sea Fever

Hi David :)

Re best time to head out, I would say anytime from April until June, after that and once it hits July it gets really humid so I would avoid at all costs.

For good anchorage spots and plannig out your trip, check out the Gunkholers guide to the Chesapeake, it’s a cruise planner with suggested itineraries but also has charts and waypoints for anchorages and key locations. It’s always very up to date too :)

Have an amazing trip!

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I am Megan Jerrard, professional travel blogger/journalist with a focus on adventure, discovery, immersion and inspiring you to explore!

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chesapeake bay Boat cruise

Cruise the Chesapeake takes great pride in being Chesapeake Bay’s favorite boat cruise company. It’s simple… Cruise the Chesapeake offers the best cruises at a great value. Our crew is fantastic. And we never compromise on our ships or safety.

Cruise the Chesapeake operations started in 2022 with the purchase of our boat, the Samantha Belle. Cruise the Chesapeake has provided visitors and locals with a true Cruise the Chesapeake boating experience. Cruise the Chesapeake is proud to provide you with lasting memories you and your friends and family will never forget.

Upcoming  Trips

April 22 2p-4p, april 29 5p-8p.

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May 1, 3, 5 9a-11am

May 24 11a-4p, july 4 8p-10p, most popular trips, sunset cruises, engagement photo shoot, small wedding ceremonies, booze cruises, public cruises, sunset cruise 2hrs, doggy cruise 1hr, singles cruise 3 hrs, byo fish gear 4hrs, magothy river cruise 3hrs, lighthouse cruise 3hrs, bay bridge & back 3 hrs, sunset cruises.

The Chesapeake Bay’s sunset is a popular time to Cruise and Cruise the Chesapeake is the local way you can experience it.   It is a stunning sunset view over the bay skyline. The golden glow reflecting off the Cruises at the horizon is a spectacular sight.

Our captain will make your trip memorable and enjoyable.   You can also bring your own food or drinks to enjoy the ambiance.

ENGAGEMENT PHOTO SHOOTS

Thrill her with a surprise engagement on a boat! If you’ve been looking for the perfect Wedding Proposal that’s unique, private, and oh-so-romantic, look no further. For the most memorable experience book a cruise where you can get down on one knee and ask her the biggest question of your life. We bet there will be a “She Said Yes!” after you pop the question.

Our crew is happy to assist by taking tons of photos for your cruise boat proposal memories that will last a lifetime.

SMALL WEDDING CEREMONIES

Do you want to tie the knot on a boat on the Chesapeake Bay and say “I do”?   Cruise the Chesapeake is a unique way to make your special day unforgettable.   You can host your dream wedding on the water at a unique venue that offers breathtaking views of Chesapeake Bay’s historical waterfront.  

Let y our dream wedding be transformed into a memorable celebration with stunning views.

Booze CRUISE

The best booze cruises are offered by us on the Chesapeake Bay! This party boat will allow you to enjoy an unforgettable experience and take in the stunning scenery of Chesapeake Bay. We want you to have a memorable boat cruise you’ll love to return to each summer. Cruise the Chesapeake is the best way to party the day away for your friends and family.

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CHESAPEAKE BAY PRIVATE CHARTERS ARE A SPECIALTY OF CRUISE THE CHESAPEAKE. FOR A NO-WORRIES ONE-STOP DAY, TELL CRUISE THE CHESAPEAKE WHAT YOU WANT AND WE TAKE CARE OF THE DETAILS!

If you’re looking for a fresh idea for your next event, why not take a whole boat cruise by yourself?   Our private charters offer a unique Chesapeake Bay experience.   This option allows you to have the whole boat for you and your group.   Our boat cruises are perfect for groups, regardless of what experience they’re looking for.   Our private boats can be hired for any occasion. We offer dynamic events set against a changing backdrop.

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The Best of the Bay

Body of VA Man who Drifted Away from Boat Recovered in Chesapeake Bay

A multi-agency search took place after a 58-year-old man drifted away from his boat. Courtesy photo provided by Master Chief Petty Officer Tim Abrams

A simple jump off the back of a boat turned tragic in Newport News last week, as a man trying to retrieve a fishing net drifted away from the boat and lost his life in the water near Buckroe Beach.

The Virginia Marine Resources Commission says the 58-year-old man, Keith Thomas Henley, was fishing aboard his boat in the Bay when he went into the water to get a dip net that had been dropped overboard. He was not wearing a life jacket, according to his friend, a passenger on the boat. The boat was anchored.

Conditions were mild at the time, with 1-3-foot seas and 10 mile-per-hour winds, according to Coast Guard Sector Virginia.

The passenger saw Henley in the water, then drifting away from his Parker cabin model boat on Thursday. The friend lost sight of him around 12:30 p.m., and tried to get the anchor up and the boat running, but struggled due to lack of familiarity with the mechanism to raise anchor or start the vessel (it had a forward and rear control). By the time the boat was underway, it was too late; Henley was no longer visible above water.

The Coast Guard deployed a 45-foot Response Boat-Medium crew and an MH-60 Jayhawk helicopter to search for the man. Multiple local emergency crews also responded. An Urgent Marine Information Broadcast to Mariners was issued for other boaters to keep a lookout.

The search continued for more than 24 hours, until the Coast Guard suspended its search at 1:40 p.m. Friday. By that point, the joint search effort had covered more than 700 square miles and a combined 80 man hours.

Along with the Coast Guard, the Hampton, Norfolk and Poquoson fire departments, Hampton Police Department, Virginia’s Marine Resources Commission and Department of Wildlife Resources and the Chambers Helo Support Command all participated in the search.

On Saturday, a charter boat crew found Henley’s body near Factory Point and Hampton Fire and Rescue recovered him.

And it’s essential for all passengers on a boat to be informed about what to do in case of an emergency, especially if the captain is incapacitated or away from the boat.

In a heartbreaking 2022 case on the Potomac River , a father and son both drowned after the boy and his sister, swimming off the boat, began to struggle in the water. The girl, 12, was saved by good Samaritans (who happened to be boating instructors). The father jumped in to save the boy, 10. The mother, who was caring for a toddler on the boat, didn’t know how to operate the boat and watched helplessly as the struggling swimmers and the boat drifted further apart. The father and son didn’t make it.

The boating instructors who saved the young girl in that case shared with Chesapeake Bay Magazine the lessons learned, including making sure a second person knows how to operate the boat.

The Virginia Marine Resources Commission agrees, and also says everyone aboard should know how to hail the Coast Guard on VHF Channel 16. Spokesman Zach Widgeon also emphasizes knowing “where your type IV throwable device is and having it readily available.” He goes on to say, “Life jackets are a must when entering the water, as it’s extremely hard to predict currents before entering.”

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Missing Ocean City Swimmer’s Body Recovered

Less than a week into May, a beach tragedy has already struck Ocean City, Maryland.

Bodies of 2 children found near location of capsized sailboat in bay of Green Bay

The bodies of two children were recovered from the bay of Green Bay on Monday morning, according to the Oconto County Sheriff's Office.

A 32-year-old Little Suamico man and his two children were reported missing after they went sailing Saturday afternoon on the bay of Green Bay.

The bodies of two children were found at 11:21 a.m. Monday, one mile south of where the boat was recovered, south of Chambers Island, according to the Oconto County Sheriff's Office.

Land, water and air searches will continue into Monday night for the missing man, with additional searches resuming in the morning as necessary, according to the Door County Sheriff's Office.

According to the U.S. Coast Guard and Oconto Sheriff's Office:

• The father and two children left Green Island in the bay at about 4 p.m. Saturday on an 18-foot sailboat.
• The three were reported missing at 12:42 p.m. Sunday after they did not arrive at their planned destination in Oconto. The Coast Guard was notified at 4:27 p.m. Sunday.
• Sunday afternoon, the father's truck and trailer were still at the boat ramp, and calls to his phone went straight to voicemail.
• A capsized "sailing vessel" was located at 6:22 a.m. Monday south of Chambers Island and was towed to Fish Creek.
• Neither the father nor the two children were found on or underneath the vessel.

Neither the Coast Guard nor the Oconto County Sheriff's Office has identified the victims.

Brown County Emergency Management identified the missing man as Bill Salnik and his two children, 3 and 5 years old.

Rashad Alexander can be contacted at [email protected].

Search for sailboat finds two children passed away; father still missing

DOOR COUNTY, Wis. (WBAY) - Two children were found dead, almost two days after a boating trip turned into a widespread search of the Bay of Green Bay.

Bill Salnik, 32, and his children, who were 3 and 5 years old, are believed to have gone sailing from Oconto near the breakwater Saturday. No one had contact with Salnik since 5 o’clock Saturday evening.

Their 18-foot sailboat was found capsized south of Chambers Island at 6:22 Monday morning during a search for the missing boaters. The bodies of the children were found five hours later. Oconto County Sheriff’s Office said the bodies of the two children were recovered about one mile south of where the boat was located.

Their names are not being released at this time pending positive identification and notification of the next-of-kin. Land, water, and air searches are continuing into the evening and additional searches will resume in the morning. This remains an active investigation, the Door County Sheriff’s Office said.

The U.S. Coast Guard is using a 45-foot boat from Sturgeon Bay and a helicopter from Traverse City to search for their father.

Investigators are looking over the sailboat after it was towed to Fish Creek and pulled out of the water by multiple law enforcement agencies. They appeared to be carrying the boat’s sail separately.

They were last seen near Egg Harbor and Green Island. They were supposedly headed for Riley’s Bay before storms hit.

The Coast Guard began a search when they were reported missing Sunday afternoon after they failed to reach their destination. The person who reported them missing said calls were going straight to voicemail and the truck and trailer for the boat were found still at the boat ramp.

The Door County Dive Team and incident command have been working out of Fish Creek since Monday morning.

The Wisconsin Air National Guard is assisting, along with sheriff’s offices in Door, Oconto and Brown counties, Oconto Fire and Rescue, Gibraltar Fire, and the Wisconsin Department of Natural Resources.

The search for the boat stretched from Green Bay to Ellison Bay.

Anyone with information about the family should contact the Sturgeon Bay Coast Guard station.

Action 2 News will continue updating this report as more information becomes available.

Copyright 2024 WBAY. All rights reserved.

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Wife recalls ‘larger than life’ outdoorsman who went overboard in Chesapeake Bay

H AMPTON, Va. (WAVY) — Ready to do more fishing, hunting and living the good life, Keith Henley was months away from the retirement that he was living for, but was not to be.

Keith Thomas Henley, 58, of Providence Forge in New Kent County, was set to retire soon from Philip Morris in Richmond. He was on a boat last week fishing, doing something he loved, when he jumped overboard to retrieve a fishing net about a mile-and-a-half from Grandview Beach in Hampton. His body has not been found and he is presumed dead.

His wife, Dawn Henley, pulled out a photo of the “classic Keith Henley” — cigarette hanging out of his mouth, a big smile on his face, standing with his hunting buddy, David Williams, known as D.W.

“D.W. called him ‘hair on fire’ because he was always going from one thing to another … and just staying busy,” Dawn Henley said.

Another photo shows Keith Henley with a 42-point deer.

It was clear he loved to hunt.

He carved ruddy, blue-billed ducks, beautiful carvings his wife was holding.

Last August, Keith Henley bought a power boat built by Parker.

One or two days before he died, he caught his largest cobia ever — there’s a picture of that too.

It was clear he loved to fish.

Then, last Thursday, July 11 Keith Henley was fishing with a co-worker when his wife got a call from the U.S. Coast Guard.

“The person said, ‘I got some bad news [for] you,'” Dawn Henley said, recalling the conversation. “‘Your husband jumped in the water to get a net’ — I was not surprised that he jumped into the water after a net. He was impulsive. I could see that happening. I could see him doing that, then saying, ‘Oh no, what have I done.’”

His friend on the boat with him was unable to get him back into the boat, and Dawn Henley said that co-worker at Philip Morris is devastated.

“I won’t say who it is — he calls all the time [and] he feels terrible,” Dawn Henley said. “He was trying to get him a rope and he just went under. He said he saw him come up and go down. He said he had to get the anchor up. I don’t think he knew how to operate the automatic anchor. He said he was about 10 yards from him — so close.”

Dawn Henley told us her husband’s friend had been in the boat before.

“Keith expected a lot from people without giving them proper instruction,” she said. “The life jackets had been put away, and I was surprised he couldn’t tread water for five minutes. I’m wondering if he had some type of a heart attack out there. We are told he died from accidental drowning.”

In the past week, Dawn Henley has been reflecting — emotional, remembering happy times with a man she knew most of her life from high school to marriage.

Towards the end of the interview Dawn got emotional.

“You know — hold on, so I would say,” she said, then clearing her throat and putting up her head.

“What flashes in my head — he was so larger than life,” she said. “He was always going from one thing to the next, trying to live life to the fullest. Now, I’m left with thinking of Keith out in the water, afraid.”

The early years

Keith and Dawn Henley were high school sweethearts.

“He was a little too old for me, so we broke up and married other people,” she said.

About 30 years later, he saw a notice of her parents’ 50-year anniversary.

“I was listed with no spouse,” she said. “So he reached out to me. He sent me a card and said, ‘Hey, if you ever want to talk about the last 30 years, give me a call.”

That call would eventually end in marriage on May 18, 2019.

“He was a nature boy,” she said. “I called him Natty Bumppo from James Fenimore Cooper’s Leather Stocking Tales. He could never get it right. He would call himself Daddy Beachamp. I said, ‘No, it’s Natty Bumppo.”

She always thought her husband had a real talent for carving, and she wished he had continued to pursue it.

“He had a lot of potential there,” she said. “In fact, we were going to enter his ducks in a competition in White Stone and then COVID hit, and they canceled the competition.”

She remembers him this way.

“Everything he did consumed him,” she said. “If he was fishing, that was his life. If he was carving, that was his life. He’s making moonshine?

“That’s his life, you know.”

Memorial Service

There will be a memorial service for Keith Henley at 2 p.m. Sunday, July 21 at the Poquoson Yacht Club, 417 Messick Road.

For the latest news, weather, sports, and streaming video, head to WAVY.com.

• The Best Small Towns on the Chesapeake Bay to Chill Out In 2024

Once the most productive estuary in the United States and amongst the top five internationally, the Chesapeake Bay's contribution to the nation's historical foundation and its natural resources is unmatched. Home to twenty million people and over 3500 species of plants and animals, this Mid-Atlantic region is one of the top vacation destinations on the East Coast. It's relaxed and chilled vibe has made it popular getaway and its appeal continues to grow in 2024. Rooted in Native American culture, this region proudly reflects its European and Indigenous influences in its architecture and town names. From its expansive seaports to its cobblestone streets, visitors are immediately enchanted. Drop anchor and learn why author James A Michener found it the ideal muse.

Cambridge MD

This original colonial settlement, dating back to 1864, has a storied history. Settled along the Choptank River as a seaport community, its role as a maritime-centric hamlet is celebrated in its museums, architecture, and well-traversed cobblestone streets.

Main Street in the town center is described as one of the most beautiful in the country. Here, you will find quaint shops that pay homage to the town's diverse heritage.

The birthplace of the founder of the Underground Railroad, Harriet Tubman , honors this brave pioneer with an interactive museum and its storytelling mosaic murals throughout the town.

For the nautical enthusiast, visit the Richardson Maritime Museum or ride on one of their many sailing vessels with fully narrated guides.

Havre De Grace MD

In 1785, General Lafayette named this town after Le Havre, France, due to its striking similarity to their French seaport. It lives up to its name, "Harbor of Grace," with its pivotal role in America's continued fight for independence during the Revolutionary War.

Its desirable position between the Susquehanna River and the Chesapeake Bay made it a destination for fishermen and seamen. With significant exports of crabs and oysters, this port gave the area an economic boom for over two centuries.

Stroll on the promenade, and you will end up at the Friends-Concord Point Lighthouse. Built in 1827, it is the second oldest in Maryland. Regarded as the heart of Havre De Grace, it was fully operational until its decommission in the 1970s. Still open for public tours, it offers some of the most stunning views on the Chesapeake.

This town is replete with museums for all kinds of tastes. One of the quirkier venues is the Havre De Grace Decoy Museum. Over 1,200 different duck decoys are on display. Anasaphilians will learn more than they ever thought they needed about these artistically crafted waterfowl.

Book a room at one of their many historic B&Bs for an extended visit. Designed in 1896, the Spencer-Silver Mansion offers modern amenities without sacrificing its original Victorian design.

Urbanna, VA

The "City of Anne" is located in Middlesex County, Virginia. Named after Queen Anne of England, this minimally populated town has much to offer in terms of homespun charm.

Set on the Rappahannock River, Urbanna is known as the oyster capital of the state. The annual oyster festival further amplifies this status. Held every fall, this town of less than 500 residents welcomes over 70,000 visitors to celebrate this saltwater delicacy.

Hampstead Farm, built in 1750, is nestled on 100 acres of farmland. This white stucco wonder has been fully restored and was a frequent stopover for George Washington. Best of all, it is available to rent for short-term stays.

Yorktown, VA

It is best known as the spot where General Cornwallis surrendered to George Washington in 1781, essentially ending the Revolutionary War. Yorktown is one of the three sites of the historic triangle of the colonial settlements.

With a rich history, this hamlet offers many opportunities to walk in the footsteps of our founding fathers. Yorktown Battlefield is the site of Washington's 1781 victory over British Forces.

Close to both Jamestown and Williamsburg , Yorktown offers access to their busier counterparts but with the luxury of returning to a more chilled vibe.

Stroll into the town center to Grace Episcopal Church, built in 1697; it counts two of the original signers of the Declaration of Independence in its congregation.

The scenic Riverwalk blends history and the contemporary with quaint shopping and dining.

Cape Charles, VA

Pennsylvanian assemblyman William Lawrence Scott founded Cape Charles, which is on the National Historic Registry. One of the first planned communities, it was designated as a railway stop between Philadelphia and Norfolk.

The Ferry system that came a few years later only cemented it as a strong connection between the north and south industrial growth. With roots in fishing, Cape Charles was one of the largest exporters of oysters and clams on the East Coast.

The original Cape Charles Lighthouse, built in 1828, was the first lighthouse on the Chesapeake Bay in Virginia. It no longer exists; however, the current lighthouse, built in 1895, offers daily tours.

Cape Charles Coastal Habitat Natural Preserve spans 50 acres. This small but vital site maintains the beaches and surrounding marshes. Public access is limited to the boardwalk but offers stunning sunset views.

For the golf enthusiast, try a round on the 18-hole Bay Creek Golf Club course. Designed by the legendary Arnold Palmer, it has been the site of multiple international competitions.

Head to Strawberry Street for local shopping and dining, as well.

Saint Michael's, MD

In Talbot County, Saint Michael's is a sought-after vacation destination. Originally designated as a trading post for tobacco farmers, it became known as "the town that fooled England" during the War of 1812. A self-imposed blackout caused the British to miscalculate their cannon fire and miss almost all structures in the town.

Take a cruise on the Patriot. In operation since 1968, this double-decker vessel offers a 2-4 hour harbor tour. Fully narrated, it is the best way to get introduced to this historic town.

Shop for fresh produce and seafood at the St. Michaels Farmers Market. This non-profit, community-based market benefits local pantries and shelters.

The Chesapeake Bay Maritime Museum sits on 18 acres of waterfront property. Home to the Hooper Strait Lighthouse, its exhibits include the nation's most comprehensive collection of Chesapeake-based artifacts.

Indulge in a local favorite, Maryland crabcakes, at the Crab Claw Restaurant on Burns Street. Then, shop for locally crafted gifts on Talbot Street.

Ocean City, MD

Situated along the Atlantic Ocean coastline, Ocean City , Maryland, is known for its family-friendly community. It is a water lover's utopia with ten miles of sandy white beaches. Whether you are fishing, surfing, or simply soaking up the sun, plenty of options are at your disposal.

Over 20 companies offer inshore and offshore fishing expeditions. White and Blue Marlin love this bay, so grab your tackle box and reel one.

Adventurers will enjoy the opportunities to parasail, kayak, and surf at novice and professional skill levels.

Seacrets Distilling Company is the first distillery opened in Worcester County since the end of prohibition in 1933. Take a tour to learn about the entire process, from grain to bottling.

Chesapeake Ghost Walks are the ideal tour for those who appreciate a bit of spooky in their holiday. Stroll down the historic area to hear tales of maritime losses of years gone by. Learn about the architecture of the local structures, all while being regaled with stories about their original occupants.

Whether you are an adventure seeker, a seafood aficionado, a beachgoer, or a history buff, there is truly something for everyone in the Chesapeake Bay. Perfect for those wanting a bit of everything in their "chill." So unplug and take a step back in time to find out why locals refer to it as their "mother of the waters." With unlimited year-round attractions, the best time to visit is now.

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