Blue Angels Performance Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDWatch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:30 am and return at 3:30 pm. Typically, we sail for a 2 hour cruise and then we anchor up front in the "spectator zone" for the best view of the performance, which usually happens around 2:00 pm.
Black-Side of the Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEngaging 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
History of Shipping in the Chesapeake Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDid you know that "ships" used to be about the size of the 74 foot Woodwind? Hard to imagine these days, join us as author and historian Dave Gendell and Mike Singer come to together to weave a path from the small ships of yesteryear to the behemoths of today. History Monday Sunset Sails occur ... Read more
Mother’s Day Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Mom away! Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage. We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Departing Annapolis Waterfront Hotel Dock at 11:00am and returning at 1:00pm. Maximum 30 guests on each sail. Includes ... Read more
The History of Annapolis – City on the Severn
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnnapolis 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
Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail away on a sunset sail. Enjoy a light snack, great cocktails (Some featuring Cruzan Rum), wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes a hummus pack, two drink vouchers, a "Cruzan" shirt and a sunset sail. Limited shirt sizes and styles. Shirts will be distributed based on reservation ... Read more
Full Moonshine Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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
Greenbury Point – Towers to the Past
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDFor 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
History of Shipping in the Chesapeake Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEver 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
Buffets, Bands and Beaches – Socializing on the Severn
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDBay 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