Schooner Woodwind

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

Latest Past Events

Sailing Cruise from Annapolis City Marina

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

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

$74.75

Schooner Race Watch

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

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

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
410-263-7837