Across the Bridge – The Importance of Eastport in the Area’s History
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDHistorically, Eastport played a vital role in the emergence of Annapolis as a commercial, legislative, and recreational landmark in the Chesapeake Bay. Learn about its history as a fort and hospital for those wtih smallpox during the Civil War, a glass factory, and boat building hub for dynasties such as the Trumpy Yachts. History Monday ... Read more
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.
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
Acoustic Brunch Sail with Gareth Asher
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with Memorial Day favorite, GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious breakfast wrap. We will only sell 30 tickets to this really special event! We do sail rain or shine. If the musicians cannot play due to the weather, but we can ... Read more
Schooners, Ketches & Yawls – Oh My
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDA multitude of vessels plow the waters of the Chesapeake Bay and the reflect both humankinds relationship with the seas, as well as in some cases specifically people's engagement with the Bay. Come learn about the evolution of sailing craft, with particular attention paid to the American experience, and the development of sailing vessels on ... 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
History of Annapolis – the City on the Severn
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnnapolis has a rich and fascinating history, from its founding in 1649 as "Providence," to the Golden Age of the 1760's and 70's, to serving as the first peacetime capital of the United States, to the founding of the U.S. Naval Academy, and onward to today. You’ll get an introduction to the city's past as ... 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
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
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