Sailing Season is Here. Join Us for a Sail!

History of Shipping in the Chesapeake Bay

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

Ever since the colonists arrived here IN SHIPS, there has been shipping. Come discuss with us, the fascinating history and differences of early local maritime shipments and how drastically different things look today. History Monday Sunset Sails occur every Monday, May-September 22. Different topics and speakers vary throughout the season. Our bar includes a selection ... Read more

Greenbury Point – Towers to the Past

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

For over the course of two world wars and well beyond, the people of Annapolis played golf next to and boated past America’s most top-secret military communication facility and didn’t have a clue they were living near our nation’s first line of defense. On our sunset sail, we will unravel the guarded government secrets that ... Read more

Full Moonshine Sail

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

Sail with us on the Chesapeake Bay while the full moon rises on the horizon plus we have added a moonshine tasting from Pathfinder Farm and Distillery. Sample three, 2-oz cocktails made with their moonshine while sailing on a classic, 74-foot schooner. When finished with the sampling you may purchase your favorite cocktails (or beer ... Read more

Sail Sip and Shuck – The Oyster Cruise

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

Set sail on the 74-foot, Schooner Woodwind for an unforgettable afternoon of oyster education and scenic beauty. Learn about oyster restoration efforts in Annapolis Harbor with our friends at Live Water Foundation, witness a live oyster cage seeding and drop demonstration, a quick lesson on how to shuck oysters and then cruise the Chesapeake Bay ... Read more

Schooner Race Watch

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

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
Schooner Woodwind
410-263-7837