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August 2020

Sunset Sail with Don Shappelle and Don Sennett

August 6 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Don Shapelle & Don Sennett performing on the Woodwind

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 and Don have a repetoire of music that everyone will enjoy while sailing aboard the magnificent Woodwind. www.donshappellemusic.com  

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Sunset Sail with Stefan Heuer Music

August 13 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Stefan Heuer (musician) holding his guitar behind his head

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 the Mid-Atlantic. ​ New singles "Amen to That" & "Gunpowder River" are available on all music platforms. Last year's album, Mother Nature Would Say, features…

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Sunset Sail with Deanna Dove

August 20 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Sunset Sail with Entertainer Deanna Dove playing guitar

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 12 years old in church and when I started writing songs they were, of course, reflections of my life and times out on the Patuxent…

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Sunset Sail with Stefan Heuer Music

August 27 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Stefan Heuer (musician) holding his guitar behind his head

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 the Mid-Atlantic. ​ New singles "Amen to That" & "Gunpowder River" are available on all music platforms. Last year's album, Mother Nature Would Say, features…

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September 2020

Sunset Sail with Eastport Oyster Boys

September 3 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Sunset sail with The Eastport Oyster Boys entertainers

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 appreciation for the Bay and its unique maritime culture and history. The Oyster Boys’ simple philosophy is wrapped up in the three basic necessities of…

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Sunset Sail with Ship’s Company

September 10 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Members of Ship's Company

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

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Sunset Sail with Ken Wenzel

September 17 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Ken Wenzel playing guitar on Woodwind

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 most recognizable, unique performers & songwriters. A saxophonist, a guitarist, a singer/songwriter, and a bandleader, Ken has been described as a purveyor of restless midwestern…

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Sunset Sail with Chris Diller

September 24 @ 5:30 pm - 7:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Chris Diller playing guitar

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 the Mid-Atlantic. ​ New singles "Amen to That" & "Gunpowder River" are available on all music platforms. Last year's album, Mother Nature Would Say, features…

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October 2020

Brunch Sail with Tony Lucca

October 4 @ 11:30 am - 2:30 pm
Annapolis City Marina, 410 Severn Ave
Annapolis,MD21403United States
Entertainer Tony Lucca

Back for an 8th performance on the Schooner Woodwind! An Intimate, Acoustic Show with TONY LUCCA aboard the 74-foot, classic schooner, Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Tony Lucca is a Nashville-based singer/songwriter whose catalog of music runs the gamut from soul-infused pop to tear-jerker folk balladry. His music has been featured in shows like “Parenthood,” “Friday Night Lights,” “Felicity,” and “Brothers and Sisters.” He was a frequent…

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