A map of points of interest along the Chesapeake Bay

Top 10 Cruising Destinations on the Chesapeake Bay

It’s no secret that the Chesapeake Bay is home to some of the best sailing destinations in the United States – Annapolis, MD is America’s Sailing Capital after all! The Cruise Annapolis charter base is situated just across from the United States Naval Academy and is one to two days of sailing away from popular stops. Charter guests delight in the ease of access to the following top ten cruising destinations:

  1. St. Michaels is a ‘must do’ stop on the Bay. It’s a charming colonial seaport town that is a favorite among sailors and their families. St. Michaels has beloved restaurants including the Inn at Perry Cabin (reservations and sharp casual clothes required). Visit the Maritime Museum and get to know the history of the Chesapeake Bay or spend the day browsing the quaint shops throughout town.
  2. Galesville is along the western shore of the West River. Getting there takes you by the Thomas Point Lighthouse, the oldest screw-pile lighthouse still in operation on the Bay. Galesville is isolated and picturesque enough to warrant cooking onboard. If you are craving dinner out, head over to Pirates Cove for seafood or Thursdays where you can enjoy your meal on the covered deck.
  3. 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 boutique shops, waterfront parks, fine restaurants, and many full-service marinas with swimming pools.
  4. Deale is a waterfront fishing village located on the Western Shore of the Bay. It’s the home of Herrington Harbor North, which has a beautiful bayside pool and 600 protected boat slips.
  5. Solomons Island is a cozy, working fishing village at the intersection of the Bay and the Patuxent River. With lots to do, Solomons Island has quickly become a favorite of all our charter guests. 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. To make the most of your trip we recommend allocating two days, during which you stop at Harrington Harbor on the way down and St. Michaels on the way back.
  6. Rock Hall is a fisherman’s town where the food is as fresh as the day’s catch. There is abundant wildlife such as bald eagles and hundreds of other bird species thanks to the Eastern Neck National Wildlife Refuge. Rock Hall also hosts many festivals and is a haven for boaters and artisans.
  7. 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’s the home of the HMS Sultana, a replica of a British Royal Navy Schooner that patrolled the east coast from 1768-1772, preventing smuggling and collecting duties.
  8. Kent Island is the largest island in the Bay and has a rich history dating back to 1631. To the east is a slim 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.
  9. The Wye River is a 16-mile tributary of the Bay, popular for its many secluded anchorages, abundant fishing, and natural beauty. There are unspoiled gunkholes along the river that make crabbing a true treat.
  10. Baltimore is a busy city-port with restaurants, shops, and attractions. There is a water taxi service available that stops at various spots such as Fort McHenry where the National Anthem was written. The National Aquarium and Camden Yards are two other fun stops!

The Cruise Annapolis fleet consists of 23 new Jeanneau and Fountaine Pajot yachts of different configurations ranging in size from 38’ to 58’ with a mix of monohulls and catamarans. Spring charter season starts in early April! Now is the time to book. Whether you’re looking for a short getaway or a 2-3-week cruising vacation, the Chesapeake Bay is among the world’s top cruising and sailing destinations. If you’re interested in booking a charter for the upcoming spring season, our Charter Specialists will be happy to help you develop a customized itinerary for your trip.