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June 2020

Sunset Sail with “R’n’R”

June 4 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
R'n'R duo performing on the Woodwind

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.

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Sunset Sail with Ken Wenzel

June 11 @ 6:30 pm - 8:30 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 Jason Ager

June 18 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Jason Ager playing guitar

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, if quirky, lyrics highlighting what it means to be a “bad guy” with groovy musical compositions that guarantee instant foot-tapping and head bobbing. www.jasonager.com www.facebook.com/jasonagermusic

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Sunset Sail with Eastport Oyster Boys

June 25 @ 6:30 pm - 8:30 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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July 2020

Sunset Sail with Ship’s Company

July 2 @ 6:30 pm - 8:30 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 Don Shappelle and Don Sennett

July 9 @ 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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July Wine in the Wind Sail

July 12 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Wine in the Wind Cheese and Bread Display

Please call office for information on tickets and updated pricing 410-263-7837 Join us for a two hour sail around the Chesapeake Bay 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…

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Sunset Sail with Eastport Oyster Boys

July 23 @ 6:30 pm - 8:30 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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Local Everything Dinner Cruise

July 26 @ 6:30 pm - 9:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Local Everything Dinner Cruise aboard Schooner Woodwind

Please call office for information on tickets and updated pricing 410-263-7837 Enjoy our “Local Everything” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally.  Our caterer, Light House Bistro, prides themselves on getting produce, meats, and many other ingredients from the local area.  For our wonderful selection of alcoholic beverages, we choose independent breweries and distilleries within a 70-mile radius.…

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Sunset Sail with Deanna Dove

July 30 @ 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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