Maryland’s Brewer’s Cup Race
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin Heavy Seas and Union Craft Breweries aboard the Sixth Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat! Union Craft vs. Heavy Seas! Battle of the Baltimore Brews. During the race, passengers (guest crew) will be able to participate in helping to sail the boat, where appropriate, of course. This will be ... 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 purchase locally or grow yourself. Tickets are $109 per adult and include three course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests. Black Ankle Vineyards will ... Read more
August Lighthouse Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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 soft drinks and snacks, $77 per adult, $50 per child. Maximum of 35 ... 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. Halter has released 6 albums, toured 50 states, and seen his popularity swell to more than 510,000 Twitter followers, 12,000 YouTube subscribers, and nearly 10,000 Facebook 'Likes'. Ernie Halter ... Read more
August Wine in the Wind
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a three hour sail around the Bay sampling wonderful wines: The Estate of Louis Latour, Burgundy with Timothe Cousins. This representative from the winery will introduce you to these special wines. 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
Old Westminster Winery 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 Old Westminster Winery at their grand opening in 2013. The proprietors, the Baker family, are raising a reputation for crafting wines of intrigue. The property is situated on a rocky plot of ground just south of historic Westminster, MD, where ... Read more
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDParticipate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds' to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a ... Read more
Acoustic Brunch with Jay Nash
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAnnouncing a Schooner Woodwind exclusive event! The influences of being on the water, enjoying great food and beverage can create great memories. However, when you combine those two elements with live music you are now on a journey. We invite you to join us as Captain Jen navigates us out of Annapolis Harbor for a ... Read more
Brews in the Breeze Lunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDJoin the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. 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 ... Read more
Annual Great Chesapeake Bay Schooner Race
Watergate Village Annapolis, MDBe part of the crew aboard the 74-foot Schooner Woodwind on the race down the Chesapeake Bay from Annapolis to Portsmouth, Virginia! Over 45 schooners participate each year. This is a once in a lifetime experience! $900 plus tax per person includes everything. Space for four guest crew members is available.