The Chesapeake Bay by Yacht

May 23, 2018

View Chesapeake Itinerary

It’s a region of majestic beauty, where natural splendor has captivated artists and writers for centuries; where thriving coastal cities profit from its resources and charming towns and islands remain rooted in time. The Chesapeake Bay whispers the story of an intriguing past and offers a cruising scene often overlooked by larger charter yachts.

Bookended by the U.S. mainland comprising Maryland, Delaware, the District of Columbia, and Virginia to the west and the Delmarva Peninsula to the east, the Chesapeake Bay is the largest estuary in North America. Averaging only 21 feet in depth, it offers deep channels to 100 feet that accommodate submarines and large commercial vessels along its 200-mile length. Fed by over 150 rivers and streams, the Bay is a haven that could be explored for days on end.

This summer, Fleet Miami will merge the luxurious amenities and service of a yacht charter with the solitude and culture of the Chesapeake Bay. Usher, the 154’ flagship yacht, will be the largest private yacht operating in the area offering week-long charters for 12 guests to discover the enchantment of the Chesapeake and the surrounding area.

Your week-long Chesapeake itinerary can be arranged to suit your interests and allow you to spend as long as you’d like in each destination. A few highlights are detailed below:



Begin or end your trip with a day or two in our nation’s capital city, Washington, DC, where culture, history and a unique local flavor collide in a wonderful array of experiences. Visit the free museums, tour the monuments, and enjoy the variety of waterfront experiences here, from the brand new District Wharf development to the always entertaining National Harbor, Georgetown’s Washington Harbour, and more.

Visit to the bustling harbor city of Baltimore, where you can be inspired by the marine life at the waterfront National Aquarium, step back in time at Fort McHenry, or watch the Orioles play at the historic Camden Yards ballpark.

Spend an afternoon exploring the delightful waterside town of Annapolis, which boasts strong sailing traditions and a thriving historic district with preserved reminders of the British colonial period.

St. Michaels is a quintessentially charming coastal town that takes pride in a rich maritime history and offers exceptional restaurants, boutique shops and eclectic galleries. This upscale town also offers plenty of cultural events during the year, and oenophiles will particularly enjoy the summer wine festivals.

With less than 1,000 inhabitants and rich maritime traditions that continue to present day, Oxford is one of the oldest towns in America. A popular boating destination, the waterfront village of Solomons Island is home to the Calvert Marine Museum, unique shops, quaint B&Bs and charming seafood restaurants.

Once a port for ferry service between Norfolk and Hampton, the old railroad town of Cape Charles, Virginia is now primarily a vacation destination sought after for its stunning beaches, signature golf courses and natural splendor. Cape Charles Historic District boasts beautiful restored homes, shops, restaurants and antique dealers. Don’t miss a visit to Eyre Hall, a plantation house that has been in the same family since 1668 and is one of the best-preserved colonial homes with gardens that are among the oldest in the U.S.

One of the eight original shires formed in colonial Virginia in 1682, Yorktown is known for its historic past, which includes being the site of famous battles during the American Revolution and the Civil War.

Uniquely preserved, Tangier Island is home to less than 500 residents and here you’ll hear the distinct accent that stems from the Old English dialect. Discovered by Captain John Smith in 1608 and claimed by the British, this island was home to freed slaves and early British settlers whose descendants remain on this tiny slip of land adrift in the middle of the Chesapeake.



Do you love seafood? You’re in luck. The Chesapeake Bay is teeming with oysters, crabs, clams and fish, which have formed the culinary basis of the region. With crab season running from April through November, you’ll not want to miss the somewhat raucous but so delicious local crab shack experience, where you’ll smash, crack and slurp crab meat smothered in Old Bay seasoning at brown paper-covered tables.

Oyster harvest season in the Chesapeake runs from October 1 – March 31, however even if you visit out of season you can still take an afternoon tour in a traditional skipjack to learn about how oysters are farmed and harvested and their importance to life in the Chesapeake Bay.

Those with seafood or shellfish aversions will thoroughly enjoy their culinary experience in the Chesapeake as well, thanks to the ever-growing number of coastal cafes and high-end fine dining experiences offering everything from authentic ethnic fare to trendy dietary-aligned dishes.

Waterfront dining is plentiful on the Chesapeake, and we recommend the award-winning Point Crab House and Grill in Annapolis or the gorgeous Oyster Farm Seafood Eatery in Cape Charles. Overlooking the York River in Yorktown, the semi-formal Riverwalk Restaurant offers a truly unforgettable dining experience featuring seafood, steak and Italian dishes.

Other culinary experiences center on the historical elements of the area. You’ll feel like you’ve stepped back in time when you sit down for dinner at the Robert Morris Inn in Oxford, which is the oldest inn in America, or cap off a day retracing history’s footsteps at Osteria 177 on historic Main Street in Annapolis.