History of Watermen on the Chesapeake
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnnapolis is known as a Seafood hub on the east coast. Most people love their Crabs and Oysters, but how many people know where their seafood comes from and how it is caught? Annapolis has been the center of the seafood industry on the Chesapeake, ride along to hear the history of Seafood and Watermen ... Read more
Black Ankle Vineyards Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain 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

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
Battle of the Severn
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDLearn the forgotten story of the lost town of “Providence”, the first Annapolis. The Battle of the Severn was a bloody skirmish fought on March 25, 1655, on the Severn River at Horn Point (today’s Eastport). It was an extension of the conflicts surrounding the English Civil War, pitting the forces of Puritan settlers against ... Read more
Legends and Lore of the Annapolis Waterfront
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAuthor and lifelong Chesapeake Bay sailor Dave 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 22. Different topics and speakers vary throughout the season. ... Read more
Fireworks Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail. We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Tickets are $149.50 per person ... Read more

Birds of the Chesapeake
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDThe Chesapeake Bay is home to hundreds of species of birds, many living close to the shores of the Severn River. Join Jack to learn about the birds of the Chesapeake, their life histories, fun facts, and see how many different species of birds you can spot on the water! History Monday Sunset Sails occur ... Read more
History of Watermen on the Chesapeake
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnnapolis is known as a Seafood hub on the east coast. Most people love their Crabs and Oysters, but how many people know where their seafood comes from and how it is caught? Annapolis has been the center of the seafood industry on the Chesapeake, ride along to hear the history of Seafood and Watermen ... Read more
What Swims Beneath Us
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnimated and entertaining tales of the fish that swims beneath the keel as we sail on the Chesapeake Bay and a modern day history of the disputes and conflicts regarding these fish. History Monday Sunset Sails occur every Monday, May-September 22. Different topics and speakers vary throughout the season. Our bar includes a selection of ... Read more
Father’s Day Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail Dad 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