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

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

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

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

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

Sailing Cruise from Annapolis City Marina

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Enjoy this rare opportunity to join us for the only public sail this weekend aboard the Woodwind II!  This 74 foot schooner was custom designed and built specifically for sailing on the Chesapeake Bay. Our bar is stocked with wine and beer, including a nice selection of local craft brews. Each trip is unique. All cruises ... Read more

Sail from the US Sailboat Show – Preview Day

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails up to four times daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is ... Read more

Event Series Sail from the US Sailboat Show

Sail from the US Sailboat Show

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is the Sailboat Boat Show? ... Read more

Event Series Sail from the US Sailboat Show

Sail from the US Sailboat Show

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is the Sailboat Boat Show? ... Read more

Event Series Sail from the US Sailboat Show

Sail from the US Sailboat Show

US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD

"Woodwind" sails daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 12th - 15th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket.  What is the Sailboat Boat Show? ... Read more

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 Woodwind
410-263-7837