And we’re sailing! Our season started in April.

Legends and Lore of the Annapolis Waterfront

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Annapolis sailor and author David Gendell brings aboard stories of Annapolis, the Naval Academy, sailing, and the people who make the Chesapeake Bay one of the world's most vibrant sailing grounds. History Monday Sunset Sails occur every Monday, May-September 24. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft ... 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 The Battle of the Severn

The Battle of the Severn

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

The Battle of the Severn, which took place off Greenbury Point in Annapolis harbor, was the only battle fought in America associated with the English Civil War (1642 - 1655), pitting Roman Catholics against Protestants. It was also the first battle ever fought between American soldiers on American soil. History Monday Sunset Sails occur every ... Read more

History of Shipping in the Chesapeake Bay

Annapolis Waterfront Hotel 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 24. Different topics and speakers vary throughout the season. Our bar includes a selection ... Read more

The War of 1812 on the Chesapeake

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

The War of 1812 is a sometimes forgotten war in American history but it helped secure the future of a young United States. You'll learn about the important role the U.S. Navy played in the conflict and the circumstances that led to the creation of one of our nation's most enduring symbols. History Monday Sunset ... Read more

Fireworks Cruise

Annapolis Waterfront Hotel 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.

$143.75

Wine in the Wind: Women in Wine

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Join us and sip on women-led wineries who have all broken ground in different ways and challenged the old guard of wine making. We invite you to raise the sails, steer the boat or sit back and relax. Wine Samples paired with "Magnificent Morsels" There will be representatives aboard to talk about the food and ... Read more

$101.20

Tunes & Tales of the Golden Age of Annapolis, 1750-1783

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

Join us on the Woodwind for a lively set of tunes & tales about life during the heyday of Annapolis (1750-1783), the social life and events that created the American Revolution. History Monday Sunset Sails occur every Monday, May-September 24. Different topics and speakers vary throughout the season. Our bar includes a selection of Craft ... Read more

Event Series The Battle of the Severn

The Battle of the Severn

Annapolis Waterfront Hotel 80 Compromise Street, Annapolis, MD

The Battle of the Severn, which took place off Greenbury Point in Annapolis harbor, was the only battle fought in America associated with the English Civil War (1642 - 1655), pitting Roman Catholics against Protestants. It was also the first battle ever fought between American soldiers on American soil. History Monday Sunset Sails occur every ... Read more

History of Shipping in the Chesapeake Bay

Annapolis Waterfront Hotel 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 24. Different topics and speakers vary throughout the season. Our bar includes a selection ... Read more

Schooner Woodwind
410-263-7837