Boating

Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Che...

Boating

Cruises on the Bay by Watermark

Cruises on the Bay by Watermark has been offering sightseeing cruises to visitors and residents of Annapolis for over 40 years! Cruises run daily through early Spring until early Fall with Special Eve...

Boating

Liberte, The Schooner

Private, personalized charters for up to 49 guests. Sail aboard Annapolis’ most spacious schooner—corporate and team-building outings, weddings and events. Call Captain Chris and entertain the pos...

Boating

Yacht Charters on the Bay by Watermark

Chartering a beautiful yacht for a corporate or social event is easy at Yacht Charters on the Bay by Watermark. With a fleet of 13 yachts from 24' to 99’, our boats are elegant, luxurious and unique...

Boating

Annapolis Sailing School

America's oldest sailing school and Annapolis' largest sailing school. Learn to sail the "Annapolis Way" from beginner to advanced. KidShip Sailing is a weekly sailing camp that offers age appropriate...

Boating

Annapolis Community Boating

Annapolis Community Boating is a 501©3 organization dedicated to creating safe, fun and educational on-the-water opportunities for the entire community. Annapolis Community Boating is constantly putt...

Boating

Annapolis Electric Boat Rentals, LLC

Enjoy the serenity and beauty of Annapolis' waterways on a Duffy electric boat, all year round! As easy to drive as a golf cart, so anyone can be their own captain.  Seats up to 10 passengers. Bring...

Boating

Eastport Yacht Club

Sailing Lessons at Eastport Yacht Club. Eastport Yacht Club is a small, sailing oriented, private club willing to host guests for seminars and social functions. The Mission of the Eastport Yacht Club ...

Boating

Island Chill Yacht Charters

We are located just 6 miles south of the yachting capital of Annapolis MD, and the ultimate cruising destination of the Chesapeake Bay. We host what are referred to as our 'Mini-Vacational Cruises' fo...

Boating

LoosenUp Charter Fishing

Maryland Chesapeake Bay Fishing ChartersLicensed for up to 44 passengers Departs out of Deale, Maryland, only a short distance out of Annapolis and Chesapeake Beach, Maryland. Fishing for Maryland St...

Boating

Rob Wagner Charters, LLC

We offer day and over night crewed charters. Come join us and enjoy a special time sailing the Chesapeake. Our 38-foot sailing catamaran, the Alana McCree, is available for crewed charters out of Libe...

Boating

South River Boat Rentals

Powerboat and sailboat rentals and charters on the Chesapeake Bay. We offer bareboat or captained charters by the half day, full day and weekly. Team building and corporate charters....