Sailing Season is Here. Join Us for a Sail!

Latest Past Events

Sunset Sail with Dirty “Little” Secret

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

Dirty Secret's founding members, Kelly Secret & Scott O'Toole, explore the acoustic side of blues with a shot of old school rock. They are the perfect pairing with a sunset and a locally brewed Heavy Seas Beer.  You have heard of beer pairings with food? How about beer & song pairings? Kelly works at Heavy ... Read more

$42.00

Brews in the Breeze Lunch Cruise

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

Join the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. 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 ... Read more

$74.00

Independence Day Sailing

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

Make your plans early for sailing on the 4th of July!  Tickets are now available for all daytime sails on July 4th.  Go sailing during the day and then stake out your spot on land to watch the Fireworks over Annapolis Harbor. Depart Annapolis for a two-hour cruise at 11:00 am, 1:30pm or 4:00pm. Cruise ... Read more

$42.00
Schooner Woodwind
410-263-7837