2024 Sailing Season is coming! See you April 13, 2024!

Acoustic Brunch Sail with Tony Lucca

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with, TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch.

$138.00

Sailor’s Delight Cocktail Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail 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

$104.65

Event Series Birds of the Chesapeake

Birds of the Chesapeake

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

The 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

Mother’s Day Brunch Sail

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail 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

$101.20

History of Shipping in the Chesapeake Bay

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Ever 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

Across the Bridge – The Importance of Eastport in the Area’s History

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Historically, 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, MD

Watch 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.

$192.05

Acoustic Brunch Sail with Gareth Asher

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An 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

$112.70

Schooners, Ketches & Yawls – Oh My

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

A 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, MD

Author 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

Schooner Woodwind
410-263-7837