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
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.
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
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
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
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
Sailor’s Delight Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail away on one of our first sunset sails of the season. Enjoy great cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail. Depart Annapolis at 5:30 pm, return at 7:30 pm. Great Assortment of Craft Beers from the Local Area, ... Read more
Acoustic Brunch Sail with Tony Lucca
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with, TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch.
Acoustic Brunch with Ernie Halter
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with, ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. 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 still sail- we ... Read more
Schooner Race Watch
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDThe Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more