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

Cap’n Mike’s Full Moon Adventures

Offering boutique charters for up to six passengers, rates begin at $500 and range up depending up the type and venue of the adventure you select: sightseeing, biking, paddleboarding, kayaking, sailb...

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

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

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...