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August 2020

August Wine in the Wind Sail

August 9 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Wine in the Wind Cheese and Bread Display

Join us for a two hour sail around the Chesapeake Bay on a 74-foot classic, schooner while sampling wonderful wines from TBD.  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 is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go…

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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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Brunch Sail with Michael Tolcher

August 30 @ 11:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Michael Tolcher crouching in front of a wall

An Intimate, All Ages Acoustic Show with MICHAEL TOLCHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Michael Tolcher 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, classic wooden schooner, Woodwind. Michael Tolcher is an American singer/songwriter that blends southern, soul, improv, sincerity and comedy all together to form his art.…

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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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Classic Wooden Boat Regatta

September 20 @ 11:00 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
The Wooden Boat Regatta in Annapolis photo by Kate Gahs

Participate in the Classic Wooden Boat Regatta. The Woodwinds' have been invited to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This…

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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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