Latest Past Events

Schooner Race Watch

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

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the 74-foot, Schooner Woodwind II. Join in the excitement and watch the start of the 130-mile race from Annapolis to Norfolk. There could be as many as 25 schooners at the starting line (maybe more!). Some of them are 100+ feet. This is going to ... Read more

$142.60

Wedding Crashers “Sacked” Brunch Sail

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

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

Fireworks Cruise

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

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