July 4th Sailing Cruises
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Away on the 4th of July for a daytime sail aboard The 74-foot schooner Woodwind, custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit ... Read more
July 4th Sailing Cruises
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Away on the 4th of July for a daytime sail aboard The 74-foot schooner Woodwind, custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit ... Read more
July 4th Sailing Cruises
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Away on the 4th of July for a daytime sail aboard The 74-foot schooner Woodwind, custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit ... Read more
Fireworks Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail. We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. **Please note - Second boat ... Read more

Wedding Crashers “Sacked” Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCan you believe its been 20 years? Enjoy a movie themed brunch tons of fun!! Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes a crab cake (of course), meatloaf (Ma's recipe), scallop wrapped in bacon and other fun themed ... Read more
Wedding Crashers Tales From Aboard
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain Jen will share stories about the filming and answer questions including what the boat was supposed to be named, where all the sites were that they sailed to, and the insight on the scene that was never shown Sail Away on the aboard the 74-foot schooner Woodwind, as seen in the movie the Wedding ... Read more
Wedding Crashers Team Trivia
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDHow much do you know about the movie? Do you know all the "Wedding Crashers" Rules? Gather your team and come test your knowledge with Captain Jen who was the captain aboard during the filming of the Woodwind scenes. (winning team will win a Woodwind Turkish Towel for each team member) (max 4 towels) Sail ... Read more
Wedding Crashers Tales From Aboard
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain Jen will share stories about the filming and answer questions including what the boat was supposed to be named, where all the sites were that they sailed to, and the insight on the scene that was never shown Sail Away on the aboard the 74-foot schooner Woodwind, as seen in the movie the Wedding ... Read more
Black Ankle Vineyards Dinner Cruise
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Acoustic Brunch Sail with Ernie Halter
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with, ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the ... Read more