Latest Past Events
October Lighthouse Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, AnnapolisSail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks, $130 per adult. Maximum of 24 ... Read more
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, AnnapolisDISCOUNTED RATE for NO LUNCH OPTION, this rate does not include the bagged lunches. We encourage you to bring a prepackaged lunch to enjoy during the sail (no buffets or displays will be allowed) Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of ... Read more
Wedding Crashers “Sacked” Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, AnnapolisCan you believe its been 15 years? Enjoy a movie themed brunch and 2 adult beverages. Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes crab cakes (of course), meatloaf & egg sliders, scallops wrapped in bacon and other fun ... Read more