Latest Past Events

June Wine in the Wind – Tommasi Family Estates

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Italy.  The representative from the winery will introduce you to four special wines while we are under sail as we explore Italy through the Tommasi Family Estates. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along ... Read more

$81.00

Sunset Sail with Crab Alley Lite

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

Crab Alley founders Jeff Holland and Janie Meneely will join up for a Woodwind cruise and regale the crew with their original songs of the Bay and beyond. Serious or saucy, their songs shed light on recreational boating as well as Chesapeake traditions here on the Bay. www.janiemeneely.com  

$46.00

Sunset Sail with Eastport Oyster Boys

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

 Appointed as the Musical Goodwill Ambassadors by the City of Annapolis and the Maritime Republic of Eastport, the Eastport Oyster Boys love to share their musical celebration and stories of life in Annapolis and on the salty waters the Chesapeake Bay. For over two decades they have educated, amused and delighted thousands with their wit, ... Read more

$46.00