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 | 158 Reviews
  • 258 Verified Bookings
  • Member Since 2008
  • 13 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.


View a list of services offered by this vendor.


Check out these verified reviews from bookings on The Bash.

Avg 5.0 | 158 Reviews

See all 158 Reviews

Review by Tara N.

Community EventReviewed on July 2, 2022From Ruskin, FL

The Island Boys were a wonderful addition to our Caribbean outdoor event. Everyone who attended enjoyed the music. Winston even took time to show some of the children how the drums worked.

Review by Rusty R.

Birthday Party (Adult)Reviewed on May 22, 2022From Sarasota, FL

Winston was awesome. He loves what he does and it comes across to the crowd. I highly recommend him to anyone looking for a great addition to your party

Review by Brandi B.

Nursing Home EventReviewed on April 26, 2022From Sarasota, FL

The Island Boys were a lot of fun, good sound, brought everything they needed for us to have a successful party. And they were on time despite traffic and construction!

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

Choose the Date of Your Event

Date Selected: 10/2/2022

Booked Events

: The Bash Verified Bookings

Upcoming Events

November 12, 2022 • Wedding Ceremony
Sat5:00 PM - 6:00 PM Indian Rocks Beach, FL
December 17, 2022 • Corporate Function
Sat3:00 PM - 6:00 PM Punta Gorda, FL
January 24, 2023 • Corporate Function
Tue11:30 AM - 1:00 PM Bradenton, FL

Past Events

September 30, 2022 • Wedding
Fri6:00 PM - 9:00 PM Saint Petersburg, FL
July 2, 2022 • Community Event
Sat3:00 PM - 6:00 PM Ruskin, FL
May 22, 2022 • Birthday Party (Adult)
Sun1:00 PM - 4:00 PM Sarasota, FL
April 26, 2022 • Nursing Home Event
Tue5:00 PM - 6:00 PM Sarasota, FL
March 30, 2022 • Celebration
Wed6:00 PM - 7:30 PM Sarasota, FL
March 19, 2022 • Wedding Ceremony
Sat5:00 PM - 6:00 PM Dunedin, FL
March 18, 2022 • Birthday Party (Adult)
Fri6:00 PM - 9:00 PM Belleair Beach, FL
March 13, 2022 • Private Party
Sun4:30 PM - 7:30 PM Naples, FL
February 23, 2022 • Corporate Function
Wed6:00 PM - 8:30 PM Tampa, FL

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