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

Sunset Sail with Eastport Oyster Boys

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

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 and special message of stewardship and ... Read more

Sunset Sail with Deanna Dove

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

Deanna Dove, Island Girl comes from Broomes Island, MD. "I grew up loving the experience of being out on the water and catching my first hard crab when I was eight years old. I have been singing just as long and sang in church with my two sisters. I started playing guitar when I was ... Read more

Sunset Sail with Don Shappelle and Don Sennett

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

Singer-songwriter and guitarist Don Shappelle along with bassist-singer Don Sennett are a dynamic duo with a positive energy and vibe that gets an audience singing along with their upbeat songs.  Tight two part harmonies and creative interplay between guitar and bass form their unique sound.  From traditional folk to songs about the Chesapeake Bay Don ... Read more

Sunset Sail with Stefan Heuer Music

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

Its all heart playing music from head to toe. ​ The energetic one-man-band has been on the road since 2014 after the release the self titled EP which includes the highly requested "Federal Hill." The music has found new life - the sound of a new wave of beach americana and alt-country music buzzing in ... Read more

Sunset Sail with Deanna Dove

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

Deanna Dove, Island Girl comes from Broomes Island, MD. "I grew up loving the experience of being out on the water and catching my first hard crab when I was eight years old. I have been singing just as long and sang in church with my two sisters. I started playing guitar when I was ... Read more

Sunset Sail with Stefan Heuer Music

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

Its all heart playing music from head to toe. ​ The energetic one-man-band has been on the road since 2014 after the release the self titled EP which includes the highly requested "Federal Hill." The music has found new life - the sound of a new wave of beach americana and alt-country music buzzing in ... Read more

Sunset Sail with Eastport Oyster Boys

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

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 and special message of stewardship and ... Read more

Sunset Sail with Ship’s Company

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

This jolly band of merrymakers has been seen and heard all up and down the east coast of the United States. Our chanteymen perform at living history events, music festivals, private parties and many other settings. www.shipscompany.org https://www.facebook.com/pages/Ships-Company-Chanteymen/69814067368

Sunset Sail with Ken Wenzel

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

Nominated for no less than FOUR Washington Area Music Awards at the 2016 30th Annual WAMMIES – for Best Roots-Rock Vocalist, Best Roots-Rock Instrumentalist, Best Roots-Rock Group (Ken Wenzel & Cross Kentucky) and Best Roots-Rock Record (...Beneath Potomac Skies) – singer/songwriter/saxophonist Ken Francis Wenzel has come into his own as one of the DC/MD/VA region’s ... Read more

Sunset Sail with Chris Diller

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

Its all heart playing music from head to toe. ​ The energetic one-man-band has been on the road since 2014 after the release the self titled EP which includes the highly requested "Federal Hill." The music has found new life - the sound of a new wave of beach americana and alt-country music buzzing in ... Read more

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