Schooner Woodwind

Thank you for a great sailing season. See you in April 2025!

Latest Past Events

Black Ankle Vineyards Dinner Cruise

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

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

Black Ankle Vineyards Dinner Cruise

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

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 (that's us). They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of ... Read more

$113.00

Everything Local Dinner Cruise

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

Enjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally.  Our caterer, Light House Bistro, prides themselves on getting produce, meats, and many other ingredients from the local area.  For our wonderful selection of alcoholic ... Read more

$113.00
410-263-7837