Latest Past Events

Friday Night Sailor’s Delight Cocktail Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail.  Depart Annapolis at 5:30 pm, return at 7:30 pm.  Tickets are $76 per adult with a maximum of ... Read more

$76.00

Dogfish Head Brews in the Breeze Brunch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis

Who says you can't have beer for breakfast? Sail on a brunch-time cruise featuring Dogfish Head Brews on the Chesapeake Bay. After we raise all our sails, a fun, Dogfish Head brewery representative will introduce you to the beer line up for the day which will pair well with our delicious pre-plated, 2 course brunch. ... Read more

$84.00

Brews in the Breeze Lunch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. After we raise all our sails, we will start the tasting with the lightest of the four beers. Lunch will consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are $84 per adult ... Read more

$84.00