Schooner Woodwind

2025 Sailing Season starts April 12th!

Tunes & Tales of the Golden Age of Annapolis (1765-1783)

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

Tom plays 18th century fiddle tunes and shares social and political insights that made Annapolis the cultural center of the Chesapeake during the colonial era. History Monday Sunset Sails occur every Monday, May-September 21. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft Beer, Wine & Bubbly available for ... Read more

The History of Annapolis – City on the Severn

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

Annapolis has a fascinating history, from its founding in 1649 as “Providence,” to the Golden Age of the 1760’s and 70’s, to the first peacetime capital of the United States, to the U.S. Naval Academy, and beyond. On this cruise, we'll hear all about the city’s past while we admire the skyline and beautiful waters ... Read more

Legends & Lore of the Annapolis Waterfront

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

Author and lifelong Chesapeake Bay sailor David Gendell brings aboard a boatload of stories of the Annapolis waterfront including the colorful personalities and events that make the waters off Annapolis one of the world’s most vibrant sailing grounds. History Monday Sunset Sails occur every Monday, May-September 21. Different topics and speakers vary throughout the season. ... Read more

Event Series History of Greenbury Point

History of Greenbury Point

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

Take a journey back to 1649 when the Puritans landed it Greenbury Point and learned about its rich history including the first naval flight and the Marconi towers! History Monday Sunset Sails occur every Monday, May-September 21. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft Beer, Wine & ... Read more

Let’s Party! Socializing on the Severn River

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

Bay Ridge Resort was developed in 1879 as a grand Victorian summer resort with a large frame hotel on the bluff near Tolly Point. Weekends were filled with USNA bands, lawn games, live animals, and frivolilties for those wealthy enough to come by ferry or rail. In the mid-1900s, Carr and Sparrow beaches were the ... Read more

Event Series History of Greenbury Point

History of Greenbury Point

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

Take a journey back to 1649 when the Puritans landed it Greenbury Point and learned about its rich history including the first naval flight and the Marconi towers! History Monday Sunset Sails occur every Monday, May-September 21. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft Beer, Wine & ... Read more

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