Sailing Season is Here. Join Us for a Sail!

Battle of the Severn

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

Learn the forgotten story of the lost town of “Providence”, the first Annapolis. The Battle of the Severn was a bloody skirmish fought on March 25, 1655, on the Severn River at Horn Point (today’s Eastport). It was an extension of the conflicts surrounding the English Civil War, pitting the forces of Puritan settlers against ... Read more

Buffets, Bands and Beaches – Socializing on the Severn

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

Bay Ridge Resort was developed in 1879 as a grand Victorian summer resort with a large frame hotel on the bluff near Tolly Point. Weekends were filled with USNA bands, lawn games, live animals, and frivolilties for those wealthy enough to come by ferry or rail. In the mid-1900s, Carr and Sparrow beaches were the ... Read more

Black Ankle Vineyards Dinner Cruise

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

Captain Jen fell in love with this winery's location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah O'Herron. They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of ... Read more

$152.95

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

The History of Annapolis – 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

On the Horizon – Annapolis Landmarks Seen from the Water

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

Four iconic buildings and areas on the Annapolis waterfront and skyline will be discussed and their historical importance: the Maryland State House, the USNA Chapel, St. Mary's Church, and the Annapolis Harbor and waterfront. There's a reason the city retains its colonial appeal and charm and much of it is tied to these four. History ... Read more

Sediment and the Chesapeake

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

Sediment is an important component of the Chesapeake Bay ecosystem. Often viewed as a pollutant due to its impact on water clarity and potential to settle on bottom dwelling flora and fauna, sediment also has positive aspects in the estuary. The talk will cover a range of sediment related topics focusing on sources (watershed, shore ... Read more

Acoustic Brunch Sail with Ernie Halter

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

An Intimate, Acoustic Show with, ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a 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 still sail- we will refund ... Read more

$129.95

The Last Days of the Schooner America Book Release Cruise

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

David Gendell's latest non-fiction book, "The Last Days of the Schooner America: A Lost Icon at the Annapolis Warship Factory" will be released in August 2024. The book reveals the extraordinary history of the iconic schooner and its unlikely but inextricable relation to the fast, focused rise of the Annapolis Yacht Yard as that facility ... Read more

Bay Ridge Queen Resort of the Chesapeake

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

A detailed account of the turn-of-the-century decades when Bay Ridge flourished as a grand Victorian resort served by steamship and train. A narrated tour of a bygone era – brought to life through enlarged photographs. History Monday Sunset Sails occur every Monday, May-September 22. Different topics and speakers vary throughout the season. Our bar includes ... Read more

Schooner Woodwind
410-263-7837