Islandboys - Steel Drum Band - Gulfport, FL - Hero Main
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Steel Drum Band from Gulfport, FL Will travel up to 500 miles

  • Avg 5.0 | 146 Reviews
  • 240 Verified Bookings
  • Member Since 2008
  • 12 Awards & Badges
  • Accepts Online Payment
  • Starting at $300 per event

About Vendor

Learn more about this vendor for your event.

The Island Boys Band Inc. is a family business consisting of Winston and his two sons Joshua and Jesse. They perform tropical steel drum music from Jamaica and the Caribbean Islands. Pop songs old and new, played with a tropical feel, perfect for that beach wedding, party, or corporate event. Have one of the best steel drum players in the area, add that "Magical Caribbean Flavor" Performing in the Tampa bay region for 20 years, The Islandboys have established a professional reputation that is unmatched. They use the highest quality sound equipment and their pans are from master pan maker Tom Reynolds of Orlando. Considering a DJ? Then Consider This! The Island Boys can play live Caribbean Island music AND DJ your favorite songs - as well as coordinate and MC the events that makeup your wedding. Winston & The Islandboys Band have played and MC'd many weddings. You can even pre-order special recordinge by your favorite artists to be played at special times. Our Goal is to make you feel like a guest at your own wedding!! (Winston...keyboards- steel drums- vocals) (Josh........steel drums- vocals) (Jesse .....steel drums) single, duo, trio, or quartet prices available upon request.


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Check out these verified reviews from bookings on The Bash.

Avg 5.0 | 146 Reviews

See all 146 Reviews

Review by Morganna F.

WeddingReviewed on June 6, 2009From Saint Petersburg, FL

Wonderful job! Winston was so nice and pleasant to do business with. Everyone loved the steel drum music at our wedding. We will definitely hire them for future events. Thank you!

Review by Jennifer M.

Memorial Day PartyReviewed on May 25, 2009From Sarasota, FL

Hiring the Island Boys was the smartest thing I did for my party -- by far. They set the stage for the event, and filled my backyard with music that transported us to the "Islands". I heard from others who want to hire them!

Review by Karen L.

Birthday Party (Adult)Reviewed on May 23, 2009From Punta Gorda, FL

Jesse of the Island Boys was fantastic. My party was a total success and Jesse provided absolutely the best music for my birthday party - Tropical Nights - Caribbean Style. His music was perfect. I've gotten many phone calls saying that my party was the best that many had ever attended. And, of course, everyone wanted to know how to reach the Island Boys should they want entertainment for their own Island Party! Great! Karen Lyons Punta Gorda, FL

Awards & Badges

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Song List

Get a feel for the songs performed by this vendor. Contact them directly for special requests.

  • Marry me | train
  • Day-o | harry belefonte
  • Jamiacan farwell | harry belefonte
  • Under the boardwalk | drifters
  • Under the sea | little mere maid
  • Yellow bird
  • Three little Birds | bob marley
  • Jammin | bob marley
  • Over the Rainbow | judy garlin
  • At the Copa | barry manilow
  • Black Magic Woman | santana
  • And I Love Her | beatles
  • Volcano | jimmy buffett
  • What a wonderful World | louie armstrong
  • Stir it up | bob marley
  • Spanish Eyes


We recommend that you contact the vendor to confirm that the event date is open.

• : Booked Events

July 2021


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Booked Events

: The Bash Verified Bookings

Upcoming Events

August 14, 2021 • Engagement Party
Sat6:30 PM - 8:30 PM Tampa, FL
October 2, 2021 • Anniversary Party
Sat4:00 PM - 7:00 PM Fort Myers, FL
October 20, 2021 • Private Party
Wed5:00 PM - 8:00 PM The Villages, FL

Past Events

July 22, 2021 • Dinner Dance
Thu5:00 PM - 7:00 PM Lady Lake, FL
July 11, 2021 • Birthday Party (Kids)
Sun12:00 PM - 3:00 PM Tampa, FL
May 14, 2021 • Celebration
Fri12:00 PM - 1:30 PM Sarasota, FL
April 24, 2021 • Private Party
Sat3:00 PM - 6:00 PM Englewood, FL
April 17, 2021 • Birthday Party (Adult)
Sat7:00 PM - 9:00 PM Saint Petersburg, FL
April 3, 2021 • Birthday Party (Adult)
Sat7:30 PM - 8:30 PM Winter Haven, FL
April 3, 2021 • Wedding
Sat5:30 PM - 7:30 PM Saint Petersburg, FL
April 2, 2021 • Community Event
Fri5:30 PM - 8:00 PM Estero, FL
March 20, 2021 • Luau Party
Sat3:00 PM - 5:30 PM Ruskin, FL

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