Annapolis Cruises - Sailing on the Chesapeake Bay

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.