Islandboys - Steel Drum Band - Gulfport, FL - Hero Main
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Islandboys Steel Drum Band from Gulfport, FL

Will travel up to 500 miles

  • Avg 5.0 | 169 Reviews
  • 284 Verified Bookings
  • Member Since 2008
  • 14 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 | 169 Reviews

See all 169 Reviews


Review by Lois W.

Birthday Party (Adult)Reviewed on August 5, 2023From Apopka, FL

Winston did I great job , professional and courteous and classy.

Review by Janet K.

Community EventReviewed on July 15, 2023From Tampa, FL

These guys were upbeat and fun which made our Calypso Pool Party a hugh success! Everyone enjoyed their sounds of the islands! Every one was dancing around the pool and had so much fun! Thank you Island Boys, we will hire them again.

Review by Renee A.

Birthday Party (Adult)Reviewed on June 4, 2023From Tampa, FL

We had a wonderful time. I would hire them again!

Awards & Badges 

See why this vendor is top rated on The Bash.

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: 9/26/2023

Booked Events 

: The Bash Verified Bookings

Upcoming Events

November 4, 2023 • Wedding Reception
Sat3:00 PM - 7:00 PM Hudson, FL
January 7, 2024 • Community Event
Sun3:00 PM - 4:00 PM Seminole, FL
January 24, 2024 • Event
Wed7:00 PM - 10:00 PM Saint Petersburg, FL
April 6, 2024 • Wedding Ceremony
Sat5:30 PM - 7:00 PM Saint Petersburg, FL

Past Events

August 5, 2023 • Birthday Party (Adult)
Sat6:30 PM - 9:00 PM Apopka, FL
August 1, 2023 • Birthday Party (Adult)
Tue6:30 PM - 8:00 PM Bradenton, FL
July 15, 2023 • Community Event
Sat5:00 PM - 7:00 PM Tampa, FL
June 30, 2023 • Celebration
Fri5:30 PM - 8:00 PM Saint Petersburg, FL
June 17, 2023 • Father's Day Party
Sat8:00 PM - 9:00 PM Brandon, FL
June 10, 2023 • Luau Party
Sat12:00 PM - 4:00 PM Tampa, FL
June 4, 2023 • Birthday Party (Adult)
Sun5:00 PM - 7:30 PM Tampa, FL
May 27, 2023 • Wedding Reception
Sat6:00 PM - 7:00 PM St Petersburg, FL

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