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Islandboys Reviews

Islandboys, profile image
  • Avg 5.0 | 157 Reviews
  • Steel Drum Band from Gulfport, FL
  • 255 Verified Bookings
  • Starting at $300 per event

157 Reviews for Islandboys

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!

Review by Mark M.

CelebrationReviewed on March 30, 2022From Sarasota, FL

Winston was great. His playing added a big chunk of fun to our party. I’d definitely hire him again.

Review by Jeff S.

Birthday Party (Adult)Reviewed on March 18, 2022From Belleair Beach, FL

Excellent! Communication was great, music was wonderful and the event was delightful because of it!

Review by brenda v.

Corporate FunctionReviewed on January 30, 2022From Port Charlotte, FL

Lovely man and great music!

Review by Rebecca W.

Private PartyReviewed on December 31, 2021From Englewood, FL

Winston from Island Boys was our steel drum player New Years Eve and he did an outstanding job! He sent a couple of reminder emails and arrived in plenty of time and set up quickly. His music was awesome, all of our friends got up to dance, Highly recommend!

Review by Erin G.

Anniversary PartyReviewed on October 2, 2021From Fort Myers, FL

What an excellent addition to our party! Winston was friendly and attentive. Definitely plan to use again.

Review by Meredith A.

Resort EventReviewed on December 18, 2021From Lake Wales, FL

Review by brenda v.

Corporate FunctionReviewed on November 21, 2021From Port Charlotte, FL

Very pleasant and professional

Review by Sarah M.

Wedding ReceptionReviewed on November 13, 2021From Bradenton, FL


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

Review by Hannah M.

WeddingReviewed on May 16, 2009From Saint Petersburg, FL

The Island Boys did a wonderful job playing at my beach wedding. Many guests came up to me and stated how cool it was that he could play Canon in D and other traditional wedding songs on the Steel Drum. Thanks for making our wedding unique!

Review by Jodi G.

Birthday Party (Kids)Reviewed on May 9, 2009From Saint Petersburg, FL

We were very pleased with the performance and professionalism of Josh (our performer) and Winston his dad, with whom we made arrangements. The music was wonderful - exactly what we wanted. Josh and Winston worked with us on the song list, the duration of the gig, and the special song requests for our daughter's birthday. The party was so successful, we extended him an hour on the spot and the guests were begging to keep him all night. We would have, but it was Josh's anniversary, so we reluctantly let him go home! We had a wonderful experience with Josh, very polite, easy going and talented! Great steel drum player!

Review by Rick S.

Wedding ReceptionReviewed on May 2, 2009From Saint Petersburg, FL

A wonderful experience. They were very professional and worked with us for all the details for our daughter's wedding. They were fantastic. Rick and Marti

Review by Deanna D.

WeddingReviewed on March 27, 2009From Clearwater, FL

Perfect in every way!

Review by Dorothy N.

Birthday Party (Adult)Reviewed on February 8, 2009From Saint Petersburg, FL

The Island Boys, Jesse, was excellent. My guests were very pleased with Jesse's performance. He was courteous and very accomadating to my guests. I recommend the Island Boys to anyone who wants a Steel Drum Band. I certainly will use the Island Boys again for my next party. Thank you Gigmasters.

Review by Mandy L.

Graduation PartyReviewed on May 16, 2009From Largo, FL

Jesse was absolutely wonderful. He was very professional and was enjoyed by everyone. It was a great addition to the graduation party and several people asked how to get in touch with him. We also recommended they go to Bilmar to hear the bad perform. Thank you so much.

Review by Krystal V.

WeddingReviewed on May 27, 2009From Sarasota, FL

First of all He was late and our guest that were supposed to be entertained for 30 minutes before the wedding were not entertained because he was not set up until 4:00. I paid the full amount anyway because once he got started he was good, but I did not get my money's worth.I deserve some free cd's or something. Also he had about 2 months to figure out where he should have been ON TIME


I have a contract signed by these clients that states a 4:00 starting time for the gig. I have a secured gigmasters bid no.509816 secured by these clients stating 4:00 as "time needed". The client states in this feedback that we started at 4:00, the exact time we agreed to start. I am very sorry that some how the client misunderstood the 4:00 starting time, that was clearly stated on two separate contracts that they read and discussed with me and signed many months before the event. I don't believe that this clients feedback reflects the truth and the fact that we started when we agreed to start and never discussed otherwise with the cli

Review by Carol C.

Birthday Party (Adult)Reviewed on December 13, 2008From Largo, FL

While the person arrived on time and was set up, the contract stated 2-15 minute breaks over 3 hours. Before the end of the first hour I found him outside on his phone and many people remarked throughout the evening that he had on the "canned" music and was not playing the drums- again he was outside on his phone. When I confronted him on the terms of the contract, he seemed to not know this. I was very disappointed and felt that I did not get my money worth. I would not hire this preformer or this group again, and would not recommend them. I feel as if i should get a partial refund, but did pay him the full amount.


After viewing the clients feedback, we immediately e-mailed & called her to sincerely apologize. Although it's no excuse, the truth was that our son, Jesse was on that cell phone because his car is broke down in Georgia since Thanksgiving. And he had arranged to go to try to get it that evening after this job and his friend who was driving had to cancel. So, he was trying to find someone else ASAP. This is why he was so distracted from this gig. Again, it's no excuse for our young son. The client was kind enough to return our call and except our apology. She didn't feel comfortable for a whole refund that we offered so we sent her half. Jesse learned a lesson!!

Review by Jennifer W.

Private PartyReviewed on July 11, 2009From Saint Petersburg, FL

Review by coleen b.

FundraiserReviewed on June 20, 2014From Safety Harbor, FL


Review by sylvia b.

Birthday Party (Adult)Reviewed on June 1, 2014From Orlando, FL

Winston was awesome! We hiref him for our bon Voyage and Birthday party. We all loved listening to him play the steel drums. Winston was prompt courteous and professional. I would rehire him for an event and I would highly recommend him to family & friends. Thank you Winston! Sylvia B.

Review by Gina P.

CelebrationReviewed on May 14, 2014From Hudson, FL

Winston was very accommodating and professional. He always returned phone calls and never caused me to worry in the least. He was early to the celebration, played for the whole 2 hours without any fuss. He was very interactive with our residents and families. They enjoyed him tremendously. I would definitely hire the Islandboys and Winston again. No complaints whatsoever. This was the easiest entertainment I have ever worked with and made for a much more enjoyable celebration for me as well. Thank You!