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

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

Acoustic Brunch Sail with Ernie Halter

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

An Intimate, Acoustic Show with, ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat.  Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the ... Read more

$121.90

Thomas Point Shoal Lighthouse Cruise

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

Sail to Thomas Point Shoal Lighthouse and learn about its history, importance, and present day condition by guest lecturer David Gendell, author of “Thomas Point Shoal Lighthouse: A Chesapeake Bay Icon” & "The Last Days of the Schooner America: A Lost Icon at the Annapolis Warship Factory" Departs Annapolis at 10:00 am and returns to ... Read more

$126.50

Schooner Race Watch

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, 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