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

Wine in the Wind: Coastal/Island Varietals

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

Join us and discover new lesser known grape varietals from the coast and islands in the Mediterranean 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 the wines. 3oz samples of each ... Read more

$101.20

Classic Wooden Boat Regatta

Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of Tradition Class". The course is a short race with laps to make the sailing close and it takes place in the Severn River. It can be up to a 3 lap race with a ... Read more

$139.15

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