Islandboys

Steel Drum Band from Gulfport, FL - Will travel up to 500 miles
135
223 VERIFIED BOOKINGS
MEMBER SINCE 2008
  ACCEPTS ONLINE PAYMENTS
BOOKED 8 days ago

$300 - $1500 per event
  ACCEPTS ONLINE PAYMENTS
About
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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100+ GigMasters Bookings
Responds quickly to client requests
A GigMasters member for 10+ years
One of the most outstanding GigMasters members for 2018!
One of the most outstanding GigMasters members for 2017!
One of the most outstanding GigMasters members for 2016!
One of the most outstanding GigMasters members for 2015!
One of the most outstanding GigMasters members for 2014!
One of the most outstanding GigMasters members for 2013!
One of the most outstanding GigMasters members for 2012!

Wedding

Overall
 
Professionalism
Accommodating
Overall Talent
Recommend

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!

(more) Review by . from Saint Petersburg, FL on

Memorial Day Party

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Professionalism
Accommodating
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Recommend

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!

(more) Review by . from Sarasota, FL on

Birthday Party (Adult)

Overall
 
Professionalism
Accommodating
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Recommend

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

(more) Review by . from Punta Gorda, FL on

Wedding

Overall
 
Professionalism
Accommodating
Overall Talent
Recommend

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!

(more) Review by . from Saint Petersburg, FL on

Birthday Party (Kids)

Overall
 
Professionalism
Accommodating
Overall Talent
Recommend

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!

(more) Review by . from Saint Petersburg, FL on

Wedding Reception

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Professionalism
Accommodating
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Recommend

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

(more) Review by . from Saint Petersburg, FL on

Wedding

Overall
 
Professionalism
Accommodating
Overall Talent
Recommend

Perfect in every way!

(more) Review by . from Clearwater, FL on

Birthday Party (Adult)

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Professionalism
Accommodating
Overall Talent
Recommend

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.

(more) Review by . from Saint Petersburg, FL on

Graduation Party

Overall
 
Professionalism
Accommodating
Overall Talent
Recommend

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.

(more) Review by . from Largo, FL on

Wedding

Overall
 
Professionalism
Accommodating
Overall Talent
Recommend

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

(more) Review by . from Sarasota, FL on

Islandboys’s Response:

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

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PAST EVENTS
FUTURE EVENTS
GIGMASTERS VERIFIED BOOKING
2019
Nov
2
Birthday Party (Adult)
Sun City Center, FL
6:00 PM - 8:00 PM
2019
Nov
9
Fundraiser
Placida, FL
4:30 PM - 8:30 PM
2019
Nov
16
Birthday Party (Adult)
Placida, FL
6:00 PM - 9:00 PM
2020
Feb
20
Fraternity Function
Palm Beach, FL
12:30 PM - 3:00 PM
2020
Apr
17
Private Party
Sarasota, FL
5:30 PM - 7:30 PM
2019
Oct
17
Rehearsal Dinner
Clearwater, FL
6:00 PM - 10:00 PM
2019
Oct
5
Club Event
Apollo Beach, FL
7:00 PM - 10:30 PM
2019
Oct
5
Corporate Function
Wesley Chapel, FL
11:00 AM - 3:00 PM
2019
Oct
1
Community Event
Saint Petersburg, FL
10:30 AM - 12:00 PM
2019
Aug
31
Birthday Party (Adult)
Riverview, FL
7:30 PM - 9:30 PM
2019
Jul
1
Wedding
Sarasota, FL
6:30 PM - 7:30 PM
2019
Jun
28
Private Party
Tampa, FL
5:00 PM - 8:00 PM
2019
Jun
15
Community Event
Pinellas Park, FL
6:00 PM - 8:30 PM
2019
Jun
1
Celebration
St Petersburg, FL
7:30 PM - 10:30 PM
2019
Jun
1
Wedding Ceremony
Bokeelia, FL
6:00 PM - 8:30 PM
2019
May
27
Club Event
Sarasota, FL
12:00 PM - 2:30 PM
2019
May
25
Private Party
Spring Hill, FL
4:00 PM - 7:00 PM
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
Caribbean Band
Oldies Band
Steel Drum Band
Beach Band
World Music Band
Wedding Band
Proms
Weddings
Baby Showers
Bar Mitzvahs
Celebrations
Funerals
Happy Hours
Picnic
Bachelorette Parties
Concerts
Bat Mitzvahs
Bridal Showers
Events
Bachelor Parties
Banquets
Christenings
Conventions
Festivals
Fundraisers
Halloween Parties
Meetings
Birthday Parties (Kids)
Birthday Parties (Adult)
First Communions
Luau Parties
Wedding Ceremonies
Wedding Receptions
Engagement Parties
Family Reunions
Rehearsal Dinners
Please note Islandboys will also travel to Saint Petersburg, Bay Pines, Pinellas Park, Largo, Clearwater, Seminole, Tampa, Indian Rocks Beach, Sun City, Belleair Beach, Anna Maria, Ruskin, Apollo Beach, Palmetto, Bradenton Beach, Bradenton, Safety Harbor, Terra Ceia, Ellenton, Cortez, Dunedin, Holmes Beach, Parrish, Gibsonton, Oldsmar, Sun City Center, Oneco, Ozona, Palm Harbor, Wimauma.
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