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 consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are $86 per adult and include lunch, two beers, and unlimited soda and water. Additional beer will be available for purchase. Children under 12 are $49 ... Read more
Fireworks Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the ... Read more
July Wine in the Wind – Masciarelli Family Estate
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Masciarelli Family Estate of Abruzzo Italy. The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is ... 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, Palate Pleasers, prides themselves on getting produce, meats, and many other ingredients from the local area. For our wonderful selection of alcoholic beverages, ... Read more
August Wine in the Wind – Along the Douro
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Portugal. The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite ... Read more
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDReduced 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. Participate in the National Sailing Hall of Fame Classic Wooden Boat ... Read more
September Wine in the Wind – Around the World, New Zealand to California
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Goldschmidt Winery, Alexander Valley & Beyond. The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine ... Read more
Brunch Sail with Ernie Halter
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, ... 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
Brews in the Breeze Lunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSail on a lunchtime cruise of beer tasting on the Chesapeake Bay. 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 $86 per adult ... Read more