Schooner Woodwind

2025 Sailing Season starts April 12th!

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

Black Ankle Vineyards Dinner Cruise

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

Captain Jen fell in love with this winery's location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah O'Herron. They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of ... Read more

$152.95
History of Watermen on the Chesapeake

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

Greenbury Point — Towers to the Past

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

Steve Carr was born and raised in Annapolis, attended the Naval Academy, and worked at the Grand Canyon for fifteen years. Steve is the author of seven books, including the very popular book about the Chesapeake, "Water Views”. He was a columnist for “Bay Weekly”. He is also a crowd-pleasing travel writer and performs on ... Read more

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

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

Legends & Lore of the Annapolis Waterfront

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

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

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