Sailing on the Chesapeake Bay is a special experience and a wonderful way to enjoy the Annapolis area. You may take a short one or two hour cruise, a half or full day cruise or even a multi-day excursion aboard a variety of sailboats. Be sure to call ahead to check on availability and remember that sailing will be best when the winds are blowing.
Schooner Woodwind Cruises - Departs from Pusser's Landing Restaurant at the Annapolis Marriott Waterfront Hotel. Two 74-foot schooners cruise the Chesapeake Bay. 2 Hour cruises depart daily and longer cruises are scheduled for special events.
Arabella Departs from City Dock. Five night cruises on the Chesapeake bay, visiting Annapolis, St. Michaels, Oxford, & Baltimore and more!
Liberte, The Schooner Private charters only. Available in the spring and fall.
Pirate Adventures on the Chesapeake This cruise is geared towards children and is a great adventure for birthday parties and special occasions. The Sea Gypsy sails from Annapolis several times a day, seven days a week.
Watermark Cruises Annapolis City Dock. Cruises range from 40-minute to 90-minute, to full day excursions. Specialties include pirate cruises, music cruises and lighthouse cruises.
The Moorings - The premier yacht charter company offers bareboat sailing, power and skippered charters on the Chesapeake Bay. The fleet will include a range of monohulls built by Beneteau and catamarans from Robertson & Caine. Cruises depart from the Annapolis Landing Marina.