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June 2019

Sunset Sail with Jason Ager

June 20 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Jason Ager sings aboard the Schooner Woodwind

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. On his third album, Porchlight, Ager’s talent as a storyteller shines as he weaves together the academic and the arcane into clever lyrics that reward the careful listener. Nestled comfortably atop classic soul, R&B,…

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Sunset Sail with Eastport Oyster Boys

June 27 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

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 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’…

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July 2019

Fireworks Cruise

$93.00
July 4 @ 6:30 pm - 10:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Tickets are $93 per adult, $66 per child and include bottled water, soft drinks, and a wide selection of desserts. Beer and wine will…

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Brunch Sail with Jesse Ruben

July 7 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

An Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Jesse Ruben is a Philly born singer/songwriter currently living in Brooklyn. His songs have been heard on TV shows such as One Tree Hill, Degrassi, Switched at Birth, and Teen Mom. His most recent single, "This Is Why I Need You", reached the top 10 in 12 different countries, and has been…

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Sunset Sail with Mike & Kelly Lange

July 11 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Mike and Kelly Lange singing on the Woodwind

Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has performed with many popular bands in the Baltimore/Washington area both as a bandleader, member, and freelance musician. His original music has been featured on numerous…

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Sunset Sail with Dirk Schwenk

July 18 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Dirk Schwenk

Dirk Schwenk is an award winning singer-songwriter from the great state of Maryland. His formal training includes years of clarinet and symphonic band, but he found rock and roll as a late-addition bass player in the High School talent show, and never went back. He has been singing, playing guitar and songwriting ever since, and has played for crowds at many of Maryland's best venues, including the Rams Head on Stage, the Recher Theater, Rams Head Live, The 8x10 and…

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Sunset Sail with Eastport Oyster Boys

July 25 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

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 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’…

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August 2019

Sunset Sail with Matt & Katie (of The Stick Mob)

August 1 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Stick Mob aboard Woodwind

Matt and Katie play with the Stick Mob, a folk-ameri-something-grass-n-stuff quintet from the hillbilly wilds of the nation's capital. They love to play and sing beautiful old melancholy tunes as well foot-stomping originals.     Band's Website https://thestickmob.bandcamp.com/ Band's Facebook Page https://www.facebook.com/pages/The-Stick-Mob/165403906811064?fref=ts

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Sunset Sail with Deanna Dove

August 8 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

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    

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Sunset Sail with Don Shappelle and Don Sennett

August 15 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States

Don Shappelle is a singer/songwriter and guitarist who grew up on the banks of the mighty Susquehanna River and sings about the people,history and boats of the Chesapeake bay and it's many beautiful rivers.  Sailing songs and sing-alongs are part of Don's repertoire and always get an audience involved.  Performing with Don Shappelle is bassist and vocalist Don Sennett.  Together these two create a unique musical style,with tight two part harmonies and creative interplay between acoustic guitar and bass. Don…

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