Schooner Woodwind

2025 Sailing Season starts April 12th!

Eastport and Its Importance to Maritime History

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

Eastport, across the Spa Creek bridge, is a peninsula rich in maritime history. It's importance during wartime involved boat building for the US and its allies. Dating back to the Civil War, it maintained a hospital for soldiers with small pox. Originally, residents were immigrants, the working class, and farmers. The community today is better ... Read more

History of Shipping in the Chesapeake Bay

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

Did you know that "ships" used to be about the size of the 70 foot Woodwind? Hard to imagine these days, join us as Mike Singer from the Baltimore and Chesapeake Bay Shipwatchers helps to weave a path from the small ships of yesteryear to the behemoths of today. History Monday Sunset Sails occur every ... 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

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

History of Watermen on the Chesapeake

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

Annapolis is known as a seafood hub on the East Coast, famous for its crabs and oysters. But how many people truly know where their seafood comes from and how it is caught? For generations, Annapolis has been at the heart of the Chesapeake Bay’s seafood industry, sustained by the hardworking watermen who have navigated ... Read more

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
Event Series Birds of the Chesapeake Bay

Birds of the Chesapeake Bay

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

Did you know that over 400 species of birds can be found throughout the Chesapeake Bay watershed? Join Jack Wildlife for a very special outing on the Chesapeake Bay in Annapolis to learn about the iconic bird species that call the Bay home, and many more fun facts and stories. You are all but guaranteed ... 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

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