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The Chesapeake Bay offers over 5,000 miles of navigable, protected coastline with an incredible diversity of cruising potential. The Bay offers forgiving conditions for beginners: a soft bottom, gentle and predictable winds, and protected harbors within easy reach of almost every corner of the Bay.


From quiet, pristine anchorages, to historic and scenic ports, to the busy port of Baltimore, to Annapolis – the sailing capital of the U.S, the Bay offers something for everyone.

The cruising season starts in early April and lasts well into November, sometimes later. Whether you are looking for a short sailing getaway, or a 2-3 week cruising vacation, the Chesapeake Bay is among the world’s top cruising and sailing destinations.

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Annapolis offers history, incredible beauty, 5-star dining, and a proud maritime tradition. One of the oldest and best preserved towns in North America, our local pubs have been visited by George Washington and other prominent figures of colonial history. The United States Naval Academy is based here, just across Spa Creek from our docks. Dining options abound, with most of the best restaurants within a 5-minute walk from our docks. From Annapolis, you are a short sail to Saint Michaels (southeast), Rock Hall (northeast), Galesville and the Rhode River (southwest) for your first night out of Annapolis.

ST. MICHAELS is a ‘must do’ stop on the Chesapeake. A charming colonial seaport town that is a favorite among sailors and their families, St. Michaels has great restaurants, including the excellent Inn at Perry Cabin (reservations and sharp casual clothes required). You can visit the Maritime Museum and get to know the history of the Bay, or just spend the day browsing the quaint shops throughout town.

GALESVILLE is along the western shore of the West River. Getting there takes you by the Thomas Point Lighthouse, the oldest screwpile lighthouse still in operation on the Chesapeake. Galesville is isolated and picturesque enough to warrant cooking out. However, if you don’t feel like cooking, there are some fun restaurants ashore. Head over to Pirates Cove for good seafood and excellent views, or check out Thursdays, where there are great views of the river from the comfortable covered deck.

OXFORD is a quiet town on the Eastern Shore that was the first port of entry into the colonial states. It sits on the mighty Choptank River and is known for its boatbuilding, quaint shops, waterfront parks, fine restaurants, and many full-service marinas with swimming pools.

DEALE is a waterfront fishing village located on the Western Shore of the Bay. It is the home to Herrington Harbor North, which has a beautiful bayside pool and 600 protected boat slips surrounded by a beautiful countryside atmosphere.

TILGHMAN ISLAND is a small quaint island with breathtaking scenery. It is on the Eastern shore at the entrance to the Choptank River. The island is separated from the mainland by Knapps Narrows and is accessed by a drawbridge. Going through the Knapps Narrow bridge is not recommended. It is shallow and narrow and there have been many groundings. It’s a great stop if you are cruising the Bay, with fresh seafood, quaint shops, museums and regular events. You can choose the Knapps Narrow Marina, or the Tilghman Island Marina to stay in while you enjoy the area.

SOLOMONS ISLAND is a cozy, working fishing village at the intersection of Chesapeake Bay and the Patuxent River. With lots to do, Solomons has quickly become a favorite of all our charters. There are plenty of great restaurants and shops as well as fossil hunting at Calvert Cliffs, the Calvert County Marine Museum and the Drum Point Screwpile Lighthouse. It is best to sail to Solomons in two days. A great itinerary is stopping at Harrington Harbor on the way down and St. Michael’s on the way back.

ROCK HALL is a fisherman’s town where the food is as fresh as the day’s catch. There is abundant wildlife, it hosts many festivals, and is a haven for boaters and artisans.

CHESTERTOWN is in the upper eastern shore on the banks of the Chester River. This charming colonial village is surrounded by the bountiful fisheries of America’s greatest estuary. It is the home of the HMS Sultana, a replica of a British Royal Navy Schooner that patrolled the American coast from 1768-1772, preventing smuggling and collecting duties.

KENT ISLAND is the largest island in the Chesapeake Bay and it has a rich history dating back to 1631. To the east is a narrow channel known as the Kent Narrows that just barely separates the island from the Delmarva Peninsula. The island has great marinas and fun places to eat, including Harris Crab House and Kentmorr Restaurant and Crab House.

THE WYE RIVER is a 16-mile tributary of the Bay. It is popular because of the many secluded anchorages, nice fishing and natural beauty. There are unspoiled gunkholes along the river that make crabbing there a treat.

BALTIMORE is a busy port with restaurants, shops, and attractions. From Harbor East Marina, you can take a water taxi to all the sites. Catch a baseball game at Orioles Park at Camden Yards, or go to the National Aquarium to see some of the 16,500 specimens.

Start planning today by contacting our Annapolis partners!

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