Latest Past Events

Cocktail Cruising

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

Sail away with great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail.  Depart Annapolis at 4:00pm, return at 6:00pm.  Tickets are $95 per adult with a maximum of 24 guests. Zoned Seating Pricing ~ Limited Capacity (24 person max): ... Read more

$95.00

October Lighthouse Cruise

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

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks, $130 per adult. Maximum of 24 ... Read more

$130.00

Sunset Sail with Chris Diller

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

Its all heart playing music from head to toe. ​ The energetic one-man-band has been on the road since 2014 after the release the self titled EP which includes the highly requested "Federal Hill." The music has found new life - the sound of a new wave of beach americana and alt-country music buzzing in ... Read more

$48.00