Schooner Woodwind

Thank you for a great sailing season. See you in April 2025!

Sunset Sail with Eastport Oyster Boys

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

Eastport Oyster Boys……..Music and Mirth of Annapolis and the Chesapeake! Appointed the Official Musical Goodwill Ambassadors by the City of Annapolis, the Eastport Oyster Boys love to share their musical celebration of life in Historical Annapolis and upon the salty waters of the Chesapeake Bay. For over two decades they have educated, amused and delighted ... Read more

Fireworks Cruise

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

Join 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

$93.00

Brunch Sail with Jesse Ruben

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

An 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

Sunset Sail with Mike & Kelly Lange

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

Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has ... 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

CANCELLED – Sunset Sail with Eastport Oyster Boys

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

This event has been cancelled because the boat has been privately chartered Eastport Oyster Boys……..Music and Mirth of Annapolis and the Chesapeake! Appointed the Official Musical Goodwill Ambassadors by the City of Annapolis, the Eastport Oyster Boys love to share their musical celebration of life in Historical Annapolis and upon the salty waters of the ... Read more

Sunset Sail with Matt & Katie (of The Stick Mob)

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

Matt and Katie play with the Stick Mob, a folk-ameri-something-grass-n-stuff quintet from the hillbilly wilds of the nation's capital. They love to play and sing beautiful old melancholy tunes as well foot-stomping originals.     Band's Website https://thestickmob.bandcamp.com/ Band's Facebook Page https://www.facebook.com/pages/The-Stick-Mob/165403906811064?fref=ts

Sunset Sail with Deanna Dove

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

Deanna Dove, Island Girl, Americana Roots Rock artist singing the stories of her life and times on the Chesapeake Bay and Patuxent River. If you like the "salt life" then these songs will speak to you. Deanna's deep and powerful voice takes control of these upbeat, lively, tongue-in-cheek songs. www.deannadove.com facebook/deannadove1    

Sunset Sail with Don Shappelle and Don Sennett

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

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 get an audience involved.  Performing with Don Shappelle is bassist ... 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

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