Schooner Woodwind

2025 Sailing Season starts April 12th!

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

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

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

Event Series Blackside of the Bay

Black-Side of the Bay

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

Engaging conversation sharing the history of the Bay's ties to the slave trade with the knowledge and skills that elevated the region's standing as a global powerhouse in the maritime and seafood industries, "Experiencing Black-joy as an Act of Resistance during Jim Crow," and growth of the areas Black middle class . History Monday Sunset ... Read more

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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