Cancelled- Sunset Sail with Don Shappelle and Don Sennett

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Cancelled due to a private event booking the whole boat.  Don Shappelle is a singer/songwriter and guitarist who grew up on the banks of the mighty Susquehanna River and sings about the people,history and boats of the Chesapeake bay and it's many beautiful rivers.  Sailing songs and sing-alongs are part of Don's repertoire and always ... Read more

Sunset Sail with Dirk Schwenk

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Dirk Schwenk is an award winning singer-songwriter from the great state of Maryland. His formal training includes years of clarinet and symphonic band, but he found rock and roll as a late-addition bass player in the High School talent show, and never went back. He has been singing, playing guitar and songwriting ever since, and ... Read more

Sunset Sail with Eastport Oyster Boys

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

 Appointed as the Musical Goodwill Ambassadors by the City of Annapolis and the Maritime Republic of Eastport, the Eastport Oyster Boys love to share their musical celebration and stories of life in Annapolis and on the salty waters the Chesapeake Bay. For over two decades they have educated, amused and delighted thousands with their wit, ... Read more

Sunset Sail with Homegrown Unplugged- Cancelled due to Private Charters

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Homegrown brings you original Americana/Alt Country rock. Dan and Tami (of Timmie & Tami, etc) will share real-life stories through the soul-soothing, gospel-infused tunes. Don't be surprised when you find yourself singing along! www.facebook.com/HomegrownAnnapolis

Sunset Sail with Jason Ager

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Jason 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

Classic Wooden Boat Regatta

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Reduced 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, MD

Join 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

$81.00

Sunset Sail with Stefan Heuer Music

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul.   Band's Website ... Read more

Brunch Sail with Ernie Halter

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An 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

$91.00

Black Ankle Vineyards Dinner Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Captain 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

$111.00