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

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 Ches...

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 45 years! Cruises run daily through early Spring until early Fall with Special Eve...

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

Crewed or Bareboat, Sail and Powerboat rentals on the Chesapeake Bay. Add paddle boards, kayaks and tubing rentals for extra fun! Light-fare food on deck! Cruise the Chesapeake and tributaries, wildli...

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

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

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...