Sailing Season is Here. Join Us for a Sail!

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

History of Annapolis – the City on the Severn

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

Annapolis 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, MD

Sail 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

$101.20
Event Series What Swims Beneath Us

What Swims Beneath Us

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

Animated 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, MD

Annapolis 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

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

Fireworks Cruise

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

Join 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

$149.50

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