Latest Past Events

Friday Night Sailor’s Delight Cocktail Cruise

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

Sail away on one of our first sunset sails of the season. Enjoy 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 5:30 pm, return at 7:30 pm.  Tickets are $78 per adult with a maximum of ... Read more

$78.00

October Lighthouse Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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 10:30am, return at 2:30pm, includes bagged lunch, soft drinks and snacks, $96 per adult, $58 per child ... Read more

$96.00

Schooner Race Watch Cruise

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

Reduced Ticket Price - not including Bagged Lunch (the order has already been placed with our caterer).  Be sure to bring your own lunch to enjoy aboard.  Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the ... Read more

$72.00