June Wine in the Wind
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 Spain. 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
Take Dad Sailing on Father’s Day
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDTake Dad sailing this year on Father's Day. We have opened our 2 hour public sails up early so you can book yourself and your "Dad" on a sail on Father's Day Now! Sailing times: 11:00-1:00 1:30-3:30 4:00-6:00 6:30-8:30 Ticket Pricing: $48/Adult $46/Senior $31/Child/Infant
Father’s Day Brunch
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDOur Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food. $94 per person, $54 per child. Maximum 35 guests. Father's Day Brunch Menu: Bacon, Ham, Caramelized Onion and Swiss Cheese ... 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
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
Brunch Sail with Jesse Ruben
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Jesse Ruben is a Philly born singer/songwriter currently living in Brooklyn. His songs have been heard on TV shows such as One Tree Hill, Degrassi, Switched at ... Read more
July Wine in the Wind
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 France. Celebrate Bastille Day as the representative from the winery introduces 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, ... 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
August Wine in the Wind
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 South America. 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, ... 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