Schooner Woodwind

Now Sailing for the 2026 Season — Book Your Cruise Today!

Special Events

Annapolis to Bermuda Ocean Race Watch Cruise

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

Watch the start of the annual Annapolis to Bermuda Ocean Race aboard the 74-foot, Schooner Woodwind. The Annapolis to Bermuda Ocean Race — or A2B — started in 1979, and covers 753 miles, making it one of the longest ocean races on the east coast of the U.S. The challenging course combines inshore and offshore, ... Read more

$151.27

Father’s Day Brunch Sail

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

Sail Dad away!  Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage. We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Departing Annapolis Waterfront Hotel Dock at 11:00am and returning at 1:00pm. Maximum 30 guests on each sail. Includes ... Read more

$111.42

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. Advance online tickets required Tickets ... Read more

$167.05
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