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

The Battle of the Severn

The Battle of the Severn

Schooner Woodwind at Annapolis Waterfront Hotel Dock 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

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
Legends and Lore of the Annapolis Waterfront

Legends and Lore of the Annapolis Waterfront

Schooner Woodwind at Annapolis Waterfront Hotel Dock 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

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

Schooner Woodwind at Annapolis Waterfront Hotel Dock 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

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 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 ... Read more

$117.30

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.

$182.85

Socializing on the Severn:  After Hour Entertainment Off the Water

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

While the Bay is well known for its significance to maritime history and the oyster industry, not all was work and no play. The tour focuses on fun after hours in the 19th/20th century, such as the Severn Rowing Club, Bay Ridge Resort, Eastport private clubs, Carr-Sparrow beaches, and the tradition of sock burning. History ... Read more

Birds of the Chesapeake Bay

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

Have you ever wondered what all the birds are doing out in the Chesapeake Bay? Look no further! Jack 'Wildlife' Turner has spent years documenting the birds of the Chesapeake Bay and beyond and is ready to fill your evening with interesting facts, bird stories, and ways that you can participate in the wonders of ... Read more

Mother’s Day Brunch

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