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

Fleet Annapolis

Relax and Stay on a Live-aboard vessel and/or Waterfront area unit Enjoy waterfront living in the Eastport area (Annapolis, MD). This Spa Creek boat is live-aboard ready! Excellent secure location ...

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 and Annapolis' largest sailing school. Learn to sail the "Annapolis Way" with classes for kids and adults of all skills levels. KidShip Sailing is a weekly sailing camp that offers a...

Boating

Annapolis Bay Charters Inc.

Annapolis Bay Charters is the original sailboat rental business in the Chesapeake Bay area. Enjoy a sailing charter vacation in and around the breathtaking coastal waters. Our agents help you choose t...

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

Chesapeake Boating Club

Enjoy unlimited use of our fleet of 23 quality sailboats and powerboats from 19 to 36 feet. Low annual fee and online reservations make boating a breeze. Stop by for a free demo....

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...