- Cape Coral, FL
- Steel Drum Band
- $250 – $2,000 per event
Drew W. said
“We really enjoyed Steely Pan, and his performance during our party was perfect. ”
Islandboys
Overview
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.
(Winston...keyboards- steel drums- vocals) (Josh........steel drums- vocals) (Jesse .....steel drums)
single, duo, trio, or quartet prices available upon request.
Reviews
36 reviews
Debra C.
June 1, 2026Highly Recommend
If you are thinking about hiring steel drums for any party, I HIGHLY recommend the Island Boys! From the first point of contact, Winston gave amazing customer service with quick responses and planning directly with the resort. The music definitely set the tone for a tropical party vibe. It made the day!
Hired as: Beach Music, Steel Drum Player
Rich G.
November 11, 2024Excellent Band Music
Everyone enjoyed the music; they were great. However, the contract read that we could keep them for an extra hour for $100, but they would not let us. They were packing up and left at 9. They need a better contract or should honor the one they have.
Hired as: Beach Music, Steel Drum Player
Jana R.
September 16, 2024Perfect music for our backyard celebration
Arrived in plenty of time to set up, very friendly and everyone at the event loved the vibe/music.
Hired as: Steel Drum Player
Sarah F.
June 18, 2024Thank You, Islandboys
It was a pleasure to work with Islandboys for a recent staff event. They were quick to communicate and arrived perfectly on time. The music was FANTASTIC! I would highly recommend these professionals for any event. Thank you!
Hired as: Steel Drum Player
Jane B.
May 10, 2024Perfect Poolside Party
Winston is the perfect steel drum entertainer! Great selection of songs, and nice to work with. Everyone enjoyed the tropical feel the music gave our event! Thanks Winston!
Hired as: Steel Drum Player
Booking information
Price range: Contact for pricing
About
The Islandboys were formed in Gulfport Fl. in 1997 by Winston and his son Joshua. In the past 12 years they have performed their popular and unique style of Island music in the greater Tamp Bay area. Perforing as a trio, duo, or solo the Islandboys have esstablished a hard earned reputation for consistenly delivering a professoinal musical package.
Jesse, Winston's youngest son joined the band in2006. He specializes in steeldrum instrumentals.
Services offered
Upcoming booked events
March 2027
23
Tuesday
Nonprofit Event
6:30pm - 6:45pm
•
Bradenton, FL
Past booked events
May 2026
29
Friday
Cocktail Party
7:00pm - 8:30pm
•
Longboat Key, FL
February 2025
22
Saturday
Cocktail Party
4:30pm - 7:00pm
•
Tampa, FL
November 2024
30
Saturday
Wedding Ceremony
6:00pm - 7:00pm
•
Sarasota, FL
09
Saturday
Dinner Party
6:00pm - 9:00pm
•
Osprey, FL
September 2024
14
Saturday
House Party
2:30pm - 4:30pm
•
Tampa, FL
July 2024
21
Sunday
Baby Shower
2:00pm - 5:00pm
•
Arcadia, FL
June 2024
17
Monday
Corporate Event
12:00pm - 1:00pm
•
Sarasota, FL
May 2024
14
Tuesday
Corporate Event
5:30pm - 7:30pm
•
Naples, FL
11
Saturday
Wedding Reception
6:00pm - 8:30pm
•
Osprey, FL
09
Thursday
Cocktail Party
5:30pm - 7:30pm
•
Clearwater Beach, FL
04
Saturday
Cocktail Party
5:00pm - 8:30pm
•
Odessa, FL
April 2024
28
Sunday
Children’s Birthday Party
1:00pm - 4:00pm
•
Tampa, FL
27
Saturday
Retirement Community Event
7:00pm - 10:00pm
•
New Port Richey, FL
March 2024
23
Saturday
Wedding Ceremony
6:00pm - 7:00pm
•
Sarasota, FL
January 2024
27
Saturday
Birthday Party
4:30pm - 6:30pm
•
Englewood, FL
July 2023
28
Friday
Reunion
6:00pm - 10:00pm
•
Nokomis, FL
May 2023
14
Sunday
Birthday Party
1:00pm - 5:00pm
•
Seminole, FL
February 2023
23
Thursday
Grand Opening
5:00pm - 7:00pm
•
Seminole, FL
January 2023
20
Friday
Wedding Ceremony
4:30pm - 5:30pm
•
St Petersburg, FL
December 2022
08
Thursday
Nonprofit Event
6:00pm - 7:30pm
•
Lakeland, FL
August 2022
20
Saturday
Birthday Party
1:00pm - 5:00pm
•
Tampa, FL
18
Thursday
Wedding Ceremony
5:30pm - 8:00pm
•
Captiva, FL
06
Saturday
Birthday Party
7:00pm - 8:00pm
•
Davenport, FL
June 2022
25
Saturday
Birthday Party
5:00pm - 8:30pm
•
Clearwater, FL
11
Saturday
Birthday Party
6:00pm - 9:00pm
•
Riverview, FL
04
Saturday
House Party
12:30pm - 2:00pm
•
Valrico, FL
March 2022
03
Thursday
Nonprofit Event
4:30pm - 6:30pm
•
Lutz, FL
January 2022
16
Sunday
Birthday Party
3:00pm - 4:00pm
•
Dunedin, FL
14
Friday
Restaurant/Bar Event
7:00pm - 10:00pm
•
Tarpon Springs, FL
December 2021
22
Wednesday
Grand Opening
5:00pm - 7:00pm
•
Lakeland, FL
October 2021
09
Saturday
Wedding Ceremony
5:00pm - 6:00pm
•
Englewood, FL
August 2021
28
Saturday
Birthday Party
7:00pm - 9:00pm
•
Spring Hill, FL
27
Friday
Dinner Party
6:00pm - 9:00pm
•
Holmes Beach, FL
June 2021
24
Thursday
Personal Occasion
5:00pm - 8:00pm
•
Redington Beach, FL
19
Saturday
Birthday Party
6:00pm - 9:00pm
•
Belleair Beach, FL
May 2021
08
Saturday
Restaurant/Bar Event
3:00pm - 6:30pm
•
Clearwater, FL
October 2020
24
Saturday
Children’s Birthday Party
6:00pm - 7:30pm
•
Tampa, FL
10
Saturday
Wedding Reception
6:00pm - 9:00pm
•
Clearwater, FL
February 2020
13
Thursday
Cocktail Party
5:30pm - 9:30pm
•
Apollo Beach, FL
November 2019
03
Sunday
Fundraiser
5:00pm - 7:30pm
•
Tampa, FL
September 2019
15
Sunday
Wedding Ceremony
6:30pm - 7:30pm
•
Sarasota, FL
April 2019
11
Thursday
Corporate Event
5:00pm - 8:00pm
•
Tampa, FL
October 2018
12
Friday
Wedding Reception
6:30pm - 9:00pm
•
Sarasota, FL
August 2018
13
Monday
School Assembly
7:00am - 8:30am
•
Auburndale, FL
July 2018
19
Thursday
Corporate Event
4:00pm - 7:00pm
•
Tampa, FL
04
Wednesday
Holiday Party
6:00pm - 8:30pm
•
Dunedin, FL
June 2018
22
Friday
Retirement Party
7:30pm - 11:00pm
•
Palm Harbor, FL
February 2018
27
Tuesday
Birthday Party
3:30pm - 6:00pm
•
Port Richey, FL
December 2017
01
Friday
Holiday Party (Christmas)
6:00pm - 9:00pm
•
Clearwater, FL
October 2017
21
Saturday
Birthday (Adult)
1:00pm - 4:00pm
•
Ruskin, FL
June 2017
22
Thursday
Surprise
6:00pm - 8:00pm
•
Siesta Key, FL
January 2017
27
Friday
Wedding Reception
6:30pm - 9:00pm
•
Sarasota, FL
October 2016
21
Friday
Wedding Ceremony
5:30pm - 6:30pm
•
Clearwater Beach, FL
July 2016
09
Saturday
Wedding Ceremony
6:00pm - 9:00pm
•
Port Charlotte, FL
April 2016
17
Sunday
Wedding Cocktail Hour
5:00pm - 7:00pm
•
St Pete Beach, FL
November 2015
08
Sunday
Wedding Reception
1:00pm - 4:00pm
•
Indian Shores, FL
October 2015
17
Saturday
Wedding Ceremony
5:00pm - 5:45pm
•
St Petersburg, FL
May 2015
30
Saturday
Holiday Party (Other)
12:00pm - 3:00pm
•
Lutz, FL
09
Saturday
Wedding Ceremony
4:30pm - 6:00pm
•
Dunedin, FL
November 2014
07
Friday
Wedding Cocktail Hour
7:00pm - 9:00pm
•
Clearwater Beach, FL
June 2014
05
Thursday
Graduation
5:00pm - 8:00pm
•
Tampa, FL
May 2014
03
Saturday
Wedding Ceremony
6:00pm - 7:30pm
•
St. Pete Beach, FL
April 2014
12
Saturday
Birthday Party
3:30pm - 7:00pm
•
Tampa, FL
04
Friday
Birthday Party
6:30pm - 8:30pm
•
Indian Rocks Beach, FL
March 2013
09
Saturday
Wedding Reception
12:30pm - 3:30pm
•
Largo, FL
Report Islandboys
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