Dinner Cruises in Annapolis

Unique dining options

Set sail aboard the most popular sailboat in Annapolis. The Woodwind offers the most unique dinner cruises aboard their 74' schooner. Enjoy delicious catering from Palate Pleasers of Annapolis as you sail the Chesapeake Bay. All food is prepared to order using only the freshest ingredients. Schooner Woodwind features special cruise options. Sail to a local crab house for a seafood feast. Wine in the Wind is a wine tasting that combines the thrill of bay breezes with refreshing wine. Brews in the Breeze provides the best selection of Maryland's craft beers.

Their most popular trip is the Boat and Breakfast. Guests will depart at sunset on Saturday for a two-hour trip around the bay. Guests then return after their separate dinner reservation for a romantic night of sailing on the water. The next morning, guests enjoy a gourmet breakfast while sailing toward Annapolis Harbor. The Schooner Woodwind is an intimate way to enjoy dining on the water.