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
Sunset Sail with Deanna Dove
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDGrowing up on Broomes Island, Maryland, Deanna Dove (a.k.a., Island Girl) is best known for her compositional writing style about her lifelong experiences on the Chesapeake Bay. Dove’s songs include elements of rock, pop, alt-country, blues and gospel, melding together with her vocal overtones to form a distinctively engaging roots rock style. Dove is a ... Read more
Sunset Sail with Jason Ager
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJason Ager is a dedicated father, a passionate college professor, and a hyper-literate original songwriter. Balancing a PhD in German Literature with a few days a week as a stay-at-home dad, Jason still plays more than 100 shows a year in the Mid-Atlantic region and beyond. On his third album, Porchlight, Ager’s talent as a ... 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
Sunset Sail with Don Shappelle
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDon Shappelle sings and writes many songs about the Chesapeake bay,it's people,it's boats and the many rivers that flow into the bay.Don grew up on the banks of the mighty Susquehanna River so many of his songs are influenced by that great river. Don also performs sailing and water oriented songs by other artists.Don Shappelle ... 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
Sunset Sail with Brandon Hardesty
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDBumpin Uglies are a polished three piece hailing from Annapolis, MD. Known for their focused approach to not taking life too seriously, Bumpin Uglies have earned a reputation as one of the hardest working bands in the land, constantly touring and perfecting their distinct sound. They also have a knack for poking fun where fun ... 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
Sunset Sail with Eastport Oyster Boys
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDRecognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and ... Read more
Sunset Sail with Ship’s Company
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDShip's Company is a living history organization dedicated to the preservation of the American maritime heritage. They interpret many aspects of maritime life between 1775 and 1865. For more than a decade, the Ship’s Company Chanteymen have shared sea salts' songs with tens of thousands, all over the East Coast. Aside from being scurvy-free, they ... Read more