Latest Past Events

Annual Great Chesapeake Bay Schooner Race

Watergate Village Annapolis

Be part of the crew aboard the 74-foot Schooner Woodwind on the race down the Chesapeake Bay from Annapolis to Portsmouth, Virginia! Over 45 schooners participate each year. This is a once in a lifetime experience! $900 plus tax per person includes everything. Space for four guest crew members is available.

$900.00

Brews in the Breeze Lunch Cruise

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

Join the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. After we raise all our sails, we will start the tasting with the lightest of the four beers. Lunch will consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are ... Read more

$78.00

Acoustic Brunch with Jay Nash

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

Announcing a Schooner Woodwind exclusive event!  The influences of being on the water, enjoying great food and beverage can create great memories.  However, when you combine those two elements with live music you are now on a journey. We invite you to join us as Captain Jen navigates us out of Annapolis Harbor for a ... Read more

$135.00