Schooner Woodwind Cruises in Annapolis, Anne Arundel County, United States | Boating

Welcome Aboard...
our two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland.
NEW! We now have easy-to-use plastic Gift Cards available for any amount.
Annapolis is "America's Sailing Capital" in the heart of the Chesapeake Bay. Help raise the sails, steer the boat, or simply sit back and relax as "Woodwind" sails from the historic waterfront, past the Naval Academy and cruises into the Chesapeake Bay.
Team Match Racing Programs
As a family business, we take great pride in making your sailing experience a memorable one.
"Woodwind" specializes in 2-hour public sailing cruises, unique longer-destination cruises each month to the Eastern Shore, waterfront crabhouses and lighthouse tours.
"Woodwind II" specializes in private charters for corporate groups, company picnics, family gatherings, birthdays, reunions and cocktail parties. We also feature an interactive and challenging team building program where "guest" crew learn how to sail and race our schooners with their colleagues.