Saturday Night Sailor’s Delight Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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
Dodon Vineyards Wine Dinner
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEstablished in 2007, the vineyards at Dodon are fortuitously situated on rolling hills just south of Davidsonville, Maryland. When they began their first experiments with 150 vines, the goal was clear: to practice sustainable agriculture and produce exceptional wines. As ninth generation custodians of this historic farmland, and as demanding winemakers, they are committed to using ... Read more
Father’s Day Brews in the Breeze Lunch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail on a lunchtime cruise on the Chesapeake Bay. Lunch will be served buffet style while sailing on the beautiful Bay! Tickets are $88 per adult and include lunch, two beers, and unlimited soda and water. Additional beer will be available for purchase. Children under 12 are $51 per person including lunch and soft drinks. Departs ... Read more
Everything Local Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEnjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally. Our caterer, Light House Bistro, prides themselves on getting produce, meats, and many other ingredients from the local area. For our wonderful selection of alcoholic ... Read more
Black Ankle Vineyards Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain 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 (that's us). They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of ... Read more
Cocktail Cruising
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSail 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 4:30pm, return at 6:30pm. Tickets are $78 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Black Bean Hummus Poblano Pimento Cheese Served with ... Read more
Brews in the Breeze Lunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDReduced Ticket Price - not including 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. Sail on a lunchtime cruise on the Chesapeake Bay. Tickets are $69 ... Read more
Cocktail Cruising
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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
Schooner Rally 2020
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCome aboard the Woodwind for a beautiful sail amongst all the schooners that are currently in Annapolis for the Parade of Schooners. We will all be sailing in the company of these other schooners for a fun, 2-hour sail. Local craft beers, wine & bubbly available for purchase aboard. Depart Annapolis at 1:30pm, return at ... Read more
Black Ankle Vineyards Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain 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