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

Acoustic Brunch Sail with Tony Lucca

Annapolis Waterfront Hotel 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

Annapolis Waterfront Hotel 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

Annapolis Waterfront Hotel 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

Annapolis Waterfront Hotel 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

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

Annapolis Waterfront Hotel 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

Annapolis Waterfront Hotel 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

Legends and Lore of the Annapolis Waterfront

Annapolis Waterfront Hotel 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

Event Series What Swims Beneath Us

What Swims Beneath Us

Annapolis Waterfront Hotel 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

Father’s Day Brunch Sail

Annapolis Waterfront Hotel 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

Annapolis Waterfront Hotel 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

Schooner Woodwind
410-263-7837