Islandboys Reviews

Avg 5.0 | 189 Reviews
Steel Drum Band from Gulfport, FL
315 Verified Bookings
Starting at $300 per event

189 Reviews for Islandboys

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Review by CHRISTINE W.

Casino Event•Reviewed on April 27, 2026•From Gainesville, FL

I would recommend their services; I had several positive comments about the music from our VIP guests.

Review by Katrina G.

Celebration•Reviewed on April 1, 2026•From Tampa, FL

Winston was a complete professional, the music was great and I highly recommend using him if you are looking for a good island steel drum vibe!!

Review by Simone C.

Celebration•Reviewed on January 28, 2026•From Saint Petersburg, FL

We had such a great experience with The Island Boys at our special event! They arrived early, handled their set up quickly, and did an amazing job filling our event with the sounds of the islands. We would definitely recommend them and would love to book with them again. Thank you for making our party so special!

Review by Jennifer G.

Cocktail Party•Reviewed on August 16, 2025•From Saint Petersburg, FL

I would hire them again in a second. Thank you so much!!

Review by James Joshua P.

Birthday Party (Adult)•Reviewed on August 5, 2025•From Tampa, FL

They put on a great show! Can wait to hire them again.

Review by Jill K.

Wedding Reception•Reviewed on June 30, 2025•From Anna Maria, FL

If you want a great vibe for any event do not look any further..... prompt... attention to details and request.... could not of envisioned a more perfect music for my wedding luncheon....thank you for making our special day even more magical

Review by Julia H.

Community Event•Reviewed on June 16, 2025•From Bradenton, FL

The Island Boys were GREAT! We hired two and the guests really enjoyed them and requested that we invite them back to the community! Super friendly, professional and talented. Highly recommend!

Review by Nick S.

Rehearsal Dinner•Reviewed on May 1, 2025•From Clearwater, FL

Winston was phenomenal from start to finish. He went above and beyond and far exceeded any expectations. He was there and set up ready to play for the full duration of the event. We had some issues with our welcome sign blowing in the wind, so he went to his car and got some tape and adhered the back to the easle. Everyone enjoyed his music and energy. He was also a pleasure to socialize with. I highly recommend you book Islandboys for your local event!!!

Review by Jennifer M.

School Assembly•Reviewed on April 25, 2025•From Palm Harbor, FL

Very happy...Island boys were great and I would use again...

Review by Ginger H.

Private Party•Reviewed on April 13, 2025•From Clermont, FL

Would hire again!!

Review by Marci W.

Corporate Function•Reviewed on December 16, 2024•From Tampa, FL

Great musician. Played a lot of familiar tunes which my guests loved. Would recommend.

Review by Michael S.

Celebration•Reviewed on October 18, 2024•From Port Charlotte, FL

The only special request we had was a few selected songs, all were honored with one song that had to be learned before the event. We Highly Recommend

Review by Shannon E.

Casino Event•Reviewed on June 21, 2024•From Port Charlotte, FL

Everyone just raved about Winston and have already asked me when I will book him again, I will be rebooking again real soon!

Review by Michael V.

Private Party•Reviewed on May 28, 2024•From Tarpon Springs, FL

Wonderful day. Cannot wait to book them again!

Review by Angie M.

Birthday Party (Kids)•Reviewed on April 14, 2024•From Sarasota, FL

We loved Winston’s performance! It was the perfect background vibe and didn’t overtake the ambiance. We could still hear each other talk while he played the drums. Everyone was excited about the songs he played. Very nice and we will be booking him again!

Review by Wendell G.

Private Party•Reviewed on April 14, 2024•From Bradenton, FL

The Islandboys exceeded expectations—They were awesome. We had close to 100 attendees and all raved about the music. Each step was flawless from initial communication, to confirmation, to set up, and performance. Thank you Islandboys for an awesome experience and kudos to The Bash for your site.

Review by Rachel L.

Wedding Ceremony•Reviewed on April 7, 2024•From Saint Petersburg, FL

The Islandboys were absolutely amazing. From beginning to end they were a pleasure to work with. They played during my cocktail hour and was the highlight of the wedding. I cannot recommend them enough!

Review by SUSIE H.

Engagement Party•Reviewed on April 2, 2024•From Clearwater, FL

If I could leave a 10 star review I would! Islandboys brought an amazing ambiance to the engagement party we had for our daughter and her fiancé. Jesse is extremely talented and stayed in constant contact to make sure our event entertainment went flawlessly. From classic calypso to modern hits, Jesse catered to all of our guests tastes of music. Hiring Islandboys was the best decision we made for this special occasion. If you are looking for exceptional live entertainment, choose Islandboys and ENJOY!

Review by AnnMarie F.

Community Event•Reviewed on January 8, 2024•From Seminole, FL

Review by Leo L.

Wedding Reception•Reviewed on November 5, 2023•From Hudson, FL

Couldn't have asked for anything better. They made our wedding even better than it already was

Review by Lois W.

Birthday Party (Adult)•Reviewed on August 7, 2023•From Apopka, FL

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

Review by Janet K.

Community Event•Reviewed on July 16, 2023•From 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 5, 2023•From Tampa, FL

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

Review by Barbie M.

Grand Opening•Reviewed on May 15, 2023•From North Port, FL

They did an amazing job! My guest and I was very pleased with their performance! They were very professional and the music was exactly what I wanted turned out perfect. My next party I will definitely book them again!

Review by Jennifer M.

Community Event•Reviewed on April 27, 2023•From Palm Harbor, FL

Fantastic for our steel drum brand. Exactly what we wanted and we will do it again in the future!

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Islandboys Reviews

189 Reviews for Islandboys