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.
36 reviews
Debra C.
June 1, 2026If 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, 2024Everyone 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, 2024Arrived 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, 2024It 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, 2024Winston 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
Price range: Contact for rates
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.
Tuesday
Nonprofit Event
6:30pm - 6:45pm
•
Bradenton, FL
Friday
Cocktail Party
7:00pm - 8:30pm
•
Longboat Key, FL
Saturday
Cocktail Party
4:30pm - 7:00pm
•
Tampa, FL
Saturday
Wedding Ceremony
6:00pm - 7:00pm
•
Sarasota, FL
Saturday
Dinner Party
6:00pm - 9:00pm
•
Osprey, FL
Saturday
House Party
2:30pm - 4:30pm
•
Tampa, FL
Sunday
Baby Shower
2:00pm - 5:00pm
•
Arcadia, FL
Monday
Corporate Event
12:00pm - 1:00pm
•
Sarasota, FL
Tuesday
Corporate Event
5:30pm - 7:30pm
•
Naples, FL
Saturday
Wedding Reception
6:00pm - 8:30pm
•
Osprey, FL
Thursday
Cocktail Party
5:30pm - 7:30pm
•
Clearwater Beach, FL
Saturday
Cocktail Party
5:00pm - 8:30pm
•
Odessa, FL
Sunday
Children’s Birthday Party
1:00pm - 4:00pm
•
Tampa, FL
Saturday
Retirement Community Event
7:00pm - 10:00pm
•
New Port Richey, FL
Saturday
Wedding Ceremony
6:00pm - 7:00pm
•
Sarasota, FL
Saturday
Birthday Party
4:30pm - 6:30pm
•
Englewood, FL
Friday
Reunion
6:00pm - 10:00pm
•
Nokomis, FL
Sunday
Birthday Party
1:00pm - 5:00pm
•
Seminole, FL
Thursday
Grand Opening
5:00pm - 7:00pm
•
Seminole, FL
Friday
Wedding Ceremony
4:30pm - 5:30pm
•
St Petersburg, FL
Thursday
Nonprofit Event
6:00pm - 7:30pm
•
Lakeland, FL
Saturday
Birthday Party
1:00pm - 5:00pm
•
Tampa, FL
Thursday
Wedding Ceremony
5:30pm - 8:00pm
•
Captiva, FL
Saturday
Birthday Party
7:00pm - 8:00pm
•
Davenport, FL
Saturday
Birthday Party
5:00pm - 8:30pm
•
Clearwater, FL
Saturday
Birthday Party
6:00pm - 9:00pm
•
Riverview, FL
Saturday
House Party
12:30pm - 2:00pm
•
Valrico, FL
Thursday
Nonprofit Event
4:30pm - 6:30pm
•
Lutz, FL
Sunday
Birthday Party
3:00pm - 4:00pm
•
Dunedin, FL
Friday
Restaurant/Bar Event
7:00pm - 10:00pm
•
Tarpon Springs, FL
Wednesday
Grand Opening
5:00pm - 7:00pm
•
Lakeland, FL
Saturday
Wedding Ceremony
5:00pm - 6:00pm
•
Englewood, FL
Saturday
Birthday Party
7:00pm - 9:00pm
•
Spring Hill, FL
Friday
Dinner Party
6:00pm - 9:00pm
•
Holmes Beach, FL
Thursday
Personal Occasion
5:00pm - 8:00pm
•
Redington Beach, FL
Saturday
Birthday Party
6:00pm - 9:00pm
•
Belleair Beach, FL
Saturday
Restaurant/Bar Event
3:00pm - 6:30pm
•
Clearwater, FL
Saturday
Children’s Birthday Party
6:00pm - 7:30pm
•
Tampa, FL
Saturday
Wedding Reception
6:00pm - 9:00pm
•
Clearwater, FL
Thursday
Cocktail Party
5:30pm - 9:30pm
•
Apollo Beach, FL
Sunday
Fundraiser
5:00pm - 7:30pm
•
Tampa, FL
Sunday
Wedding Ceremony
6:30pm - 7:30pm
•
Sarasota, FL
Thursday
Corporate Event
5:00pm - 8:00pm
•
Tampa, FL
Friday
Wedding Reception
6:30pm - 9:00pm
•
Sarasota, FL
Monday
School Assembly
7:00am - 8:30am
•
Auburndale, FL
Thursday
Corporate Event
4:00pm - 7:00pm
•
Tampa, FL
Wednesday
Holiday Party
6:00pm - 8:30pm
•
Dunedin, FL
Friday
Retirement Party
7:30pm - 11:00pm
•
Palm Harbor, FL
Tuesday
Birthday Party
3:30pm - 6:00pm
•
Port Richey, FL
Friday
Holiday Party (Christmas)
6:00pm - 9:00pm
•
Clearwater, FL
Saturday
Birthday (Adult)
1:00pm - 4:00pm
•
Ruskin, FL
Thursday
Surprise
6:00pm - 8:00pm
•
Siesta Key, FL
Friday
Wedding Reception
6:30pm - 9:00pm
•
Sarasota, FL
Friday
Wedding Ceremony
5:30pm - 6:30pm
•
Clearwater Beach, FL
Saturday
Wedding Ceremony
6:00pm - 9:00pm
•
Port Charlotte, FL
Sunday
Wedding Cocktail Hour
5:00pm - 7:00pm
•
St Pete Beach, FL
Sunday
Wedding Reception
1:00pm - 4:00pm
•
Indian Shores, FL
Saturday
Wedding Ceremony
5:00pm - 5:45pm
•
St Petersburg, FL
Saturday
Holiday Party (Other)
12:00pm - 3:00pm
•
Lutz, FL
Saturday
Wedding Ceremony
4:30pm - 6:00pm
•
Dunedin, FL
Friday
Wedding Cocktail Hour
7:00pm - 9:00pm
•
Clearwater Beach, FL
Thursday
Graduation
5:00pm - 8:00pm
•
Tampa, FL
Saturday
Wedding Ceremony
6:00pm - 7:30pm
•
St. Pete Beach, FL
Saturday
Birthday Party
3:30pm - 7:00pm
•
Tampa, FL
Friday
Birthday Party
6:30pm - 8:30pm
•
Indian Rocks Beach, FL
Saturday
Wedding Reception
12:30pm - 3:30pm
•
Largo, FL
Steel Drum Player
