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

Acoustic Brunch Sail with Tony Lucca

Schooner Woodwind at Annapolis Waterfront Hotel Dock 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

Acoustic Brunch 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 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 sail- we ... Read more

$129.95

Schooner Race Watch

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

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more

$125.35

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 rolling ... Read more

$148.35

The History of Annapolis — The City on the Severn

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

Annapolis has a fascinating history, from its foundation in 1649 as Providence, to the "Golden Age" of the 1770's, to its brief role as first peacetime capital of the United States in 1783, the founding of the U.S. Naval Academy, and onward to today. You'll get an introduction to this town's fascinating past, all within ... Read more

History of oysters on the Bay and how water quality affects them

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

Learn more about oysters, from growing habitats to different types of oysters and how water quality affect them. Learn about the Severn River Association’s water quality monitoring, its history, and how it impacts the health of our water in general. Learn how this monitoring gives us the scientific facts to know where to ‘plant’ new ... Read more

Friendship and Strife on the 17th-century Chesapeake Bay

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

Early Maryland history is a fascinating mix of rivalry, conflict, and coexistence. This talk will focus on A) the rivalry between the proprietary government of Lord Baltimore and the Kent Island settlement led by William Claiborne, B) the Battle of the Severn (1655) between rival factions from St. Mary's and Annapolis, which has been called ... Read more

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

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

History of oysters on the Bay and how water quality affects them

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

Learn more about oysters, from growing habitats to different types of oysters and how water quality affect them. Learn about the Severn River Association’s water quality monitoring, its history, and how it impacts the health of our water in general. Learn how this monitoring gives us the scientific facts to know where to ‘plant’ new ... Read more

Schooner Woodwind
410-263-7837