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May 2020

Sunset Sail with Stefan Heuer Music

May 7 @ 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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Mother’s Day Brunch Sail

May 10 @ 11:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Mothers Day Brunch Sail

Sail Mom away for the morning!  Guests can raise the sails, steer the boat, or just sit back and relax with a cold beverage.  We sail past the Naval Academy and into the Chesapeake Bay. Fun for the whole family. Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 11:30 am and returns at 2:30 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food $94 per person, $54 per child. Maximum 35…

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Sunset Sail with “R’n’R”

May 14 @ 5:30 pm - 7:30 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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Blue Angels Performance Cruise

$115.00
May 20 @ 11:30 am - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Blue Angels flying in formation

Watch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:30 am and return at 3:30 pm. Typically, we sail for a 2 hour cruise and then we anchor up front in the "spectator zone" for the best view of the performance which usually happens around 2:00 pm. Advanced ticket purchase required, includes bagged lunch, soda, and snacks; $115 per person, $75 per child w/child's lunch. Maximum 40 guests.     Gourmet Bagged…

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Sunset Sail with Don Shappelle and Don Sennett

May 21 @ 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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Acoustic Brunch Sail with Gareth Asher

May 25 @ 10:30 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis,MD21401United States
Entertainer Gareth Asher

An Intimate, Acoustic Show with Memorial Day favorite, GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Music has the power to transport us to another time and place. Gareth Asher loves to harness that power one song at a time and deliver a piece of it directly to you with every performance. His voice will captivate you immediately, and his messages of hope and healing will send your senses soaring to…

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Sunset Sail with Jason Ager

May 28 @ 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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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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June Wine in the Wind

June 14 @ 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 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 Vino with the Woodwind's logo on it.…

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