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If you see this badge on a charter or captain’s profile, that means our team has conducted a basic check using the information available in publicly available databases such as:

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This charter can take you boating over 9 miles offshore (Gulf of Mexico) and over 3 miles offshore (Atlantic) into federal waters.

This charter can take you boating up to 9 miles offshore (Gulf of Mexico) and up to 3 miles offshore (Atlantic) into state waters.

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Popular Sailing, Catamaran & Gulet Tours Charters in Chesapeake Bay  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sailing, Catamaran & Gulet Tours in Chesapeake Bay- BoatBooker

Chesapeake Bay

Chesapeake Bay, United States

chesapeake-bay

Set sail on an unforgettable 8-hour adventure! You’ll gain hands-on experience with rigging, tying knots, raising and lowering sails, and trimming them for peak performance. Learn the art of navigation, running the diesel engine, and anchoring and docking the boat like a pro. By day’s end, you'll have a solid understanding of all aspects of sailing, from start to finish, with memories of an immersive and thrilling journey on the water.

United States

AM Services

Hampton

Experience the charm and comfort of the 1978 Ericson 34T Sailing Yacht &quot;AM Services,&quot; expertly restored in 2018 for a modern and smooth sailing experience. Based out of the scenic Hampton, VA, this classic yacht is perfect for a memorable day on

Enjoy a 4-hour sunset cruise departing from the Magothy River in Arnold, sailing across the stunning Chesapeake Bay. Relax on deck as golden-hour light reflects over calm waters, with beautiful coastal views, local wildlife, and a peaceful Maryland evening on the water.

Annapolis Host & Sailing Adventures

Arnold

Set sail with Annapolis Host &amp; Sailing Adventures aboard a beautifully restored 1987 Hylas 45 Sailing yacht (refit in 2025), departing from Arnold. Perfect for up to 6 guests, this elegant vessel combines classic sailing performance with modern comfor

Get ready to sail the Chesapeake Bay aboard Optimystic, enjoying a relaxed and scenic sailing experience out of Baltimore. This trip offers a chance to take in beautiful waterfront views, fresh air, and the calm rhythm of sailing as you glide across one of the most iconic bays in the U.S. Perfect for unwinding on the water and experiencing Baltimore from a different perspective.s

Make a Memory on Optimystic

Baltimore

Make a Memory on Optimystic, a beautifully maintained 2004 Hunter 41AC sailing yacht based in Baltimore. Designed for comfort, relaxation, and unforgettable moments on the water, this elegant vessel accommodates up to 6 guests, perfect for private sailing

Sailing, Catamaran & Gulet Tours in Chesapeake Bay

Top Sailing, Catamaran & Gulet Tours in Chesapeake Bay