Schooner Woodwind

2025 Sailing Season starts April 12th!

Special Events

July 4th Sailing Cruises

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

Sail 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, MD

Sail 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, MD

Sail 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, MD

Join 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

$149.50

Wedding Crashers “Sacked” Brunch Sail

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

Can 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

$102.07

Wedding Crashers Tales From Aboard

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

Captain 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, MD

How 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, MD

Captain 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

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

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$152.95

Acoustic Brunch Sail with Ernie Halter

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

An 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

$129.95
410-263-7837