2024 Sailing Season is coming! See you April 13, 2024!

Sunset Sail with Ken Wenzel

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

With the release of  “…Beneath Potomac Skies”  -  a 12-song, full-band collection of moments and memories culled from time spent in Washington DC, and many other locales – singer/songwriter/saxophonist Ken Francis Wenzel is eager to introduce his own roots-rock, country jazz-tinged take on love, learning, and life in contemporary America. Featuring several guest appearances from ... Read more

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

Sunset Sail with “R’n’R”

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

Capt Ron and Ray have been playing together for over a year in the Annapolis music groups Burlwood and Deep Fried Ribs. Their unique takes on classic blues and country tunes make you want to kick back and enjoy the music. The shared love of artists like the Allman Brothers, Waylon Jennings and Johnny Paycheck ... Read more

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    

CANCELLED – Sunset Sail with “The Roadside”

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

CANCELLED - BOTH BOATS PRIVATELY CHARTERED The Roadside is a blue's influenced, roots-rock acoustic band that features music from the turn of the century to modern day hits. Band's website: www.theroadsideband.com Band's Facebook Page: www.facebook.com/theroadsideband

Sunset Sail with Stefan Heuer Music

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

Facebook LIVE stream of this Event Stefan Heuer is a signature Breedlove artist residing in Annapolis, MD. Heuer blends elements of Motown, Soul, and RnB in his original and cover music. His debut EP entitled "Jungle Dreams" is a sonic portrayal of his journey through losing a loved one. Stefan frequently performs all over the ... Read more

Eastport Oyster Boys

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

Facebook LIVE stream of this Event Appointed 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 on the Chesapeake Bay. For over two decades they have educated, amused and delighted thousands with their wit, wisdom ... Read more

Sunset Sail with Don Shappelle

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

Facebook LIVE stream of this Event Singer-songwriter and guitarist Don Shappelle has a positive energy and vibe that gets an audience singing along with their upbeat songs.  From traditional folk to songs about the Chesapeake Bay Don has a repertoire of music that everyone will enjoy while sailing aboard the magnificent Woodwind, and virtually. www.donshappellemusic.com ... Read more

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. Ager’s recent EP, Bad Guy - EP, features witty, ... Read more

Sunset Sail with “R’n’R”

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

Formed out of the local Annapolis band Burlwood and Deep Fried Ribs. The R’n’R Treatment is a stripped down acoustic duo featuring Russell Jacobsen and Ron Mcmorrow. They’ll make you smile and tap your toes with renditions of classic rock, blues and outlaw country covers.

Schooner Woodwind
410-263-7837