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
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
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
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
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
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.
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
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, 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
Legends & Lore of the Annapolis Waterfront
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAuthor 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
The Battle of the Severn
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSteve 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