

Gilligan's Island Bar & Grill
Gilligan's Tiki Bar:
Siesta Key’s Live entertainment destination!
Immerse yourself in the vibrant atmosphere of Siesta Key’s favorite tropical escape, where every moment feels like a vacation.
Step into a world of vibrant energy and tropical delights at Gilligan’s Island Bar, where the island spirit comes alive with every sip and bite.
Whether you’re a local or just passing through, our tiki bar offers an unforgettable escape filled with refreshing cocktails, mouthwatering dishes, and the best live entertainment on Siesta Key.
Don’t miss out on the ultimate island experience; Join us today and let the good times roll!
Siesta Key’s Live entertainment destination!
Immerse yourself in the vibrant atmosphere of Siesta Key’s favorite tropical escape, where every moment feels like a vacation.
Step into a world of vibrant energy and tropical delights at Gilligan’s Island Bar, where the island spirit comes alive with every sip and bite.
Whether you’re a local or just passing through, our tiki bar offers an unforgettable escape filled with refreshing cocktails, mouthwatering dishes, and the best live entertainment on Siesta Key.
Don’t miss out on the ultimate island experience; Join us today and let the good times roll!

Upcoming Events
Artist | Date | ||
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
MadKap Independance Day Revolution!!
Fri, July 4 6:00pm - 10:00pm |
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J Santi
Blues, Country, R&B/Soul, Rock |
Solo Acoustic
Sun, July 6 1:00pm - 5:00pm |
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Dana Lawrence of Kettle of Fish
Acoustic, Americana, Folk, Rock |
Duo!!
Wed, July 9 6:00pm - 10:00pm |
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J Santi
Blues, Country, R&B/Soul, Rock |
J Santi & the Vital Groove
Fri, July 11 6:00pm - 10:00pm |
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Groove This
Blues, Funk, R&B/Soul, Reggae |
Groove This! on Siesta Key!
Sun, July 13 6:00pm - 10:00pm $0 |
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Kettle Of Fish
Rock, Rockin Blues, Southern Rock |
Sat, July 19
6:00pm - 10:00pm |
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Wayne DeLair
Contemporary, Easy Listening, R&B/Soul, Reggae |
Good Music, Great Fun, Shared Moments!
Sun, July 20 1:00pm - 5:00pm $0 |
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Wayne DeLair
Contemporary, Easy Listening, R&B/Soul, Reggae |
Good Music, Great Fun, Shared Moments!
Fri, July 25 1:00pm - 5:00pm $0 |
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Schmitz Brothers Band
Classic Rock |
Sat, July 26
1:00pm - 5:00pm |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
MadKap at Gilligans
Fri, August 1 6:00pm - 10:00pm |
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J Santi
Blues, Country, R&B/Soul, Rock |
Solo Acoustic
Sun, August 3 1:00pm - 5:00pm |
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Johnny D and The Rockett 88's
60's Beach Rock, Americana, Rock, Rockabilly |
Johnny D on the Key!
Fri, August 8 6:00pm - 10:00pm $None |
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Weekend Agenda
Alternative, High Energy Dance, Pop, Rock |
Weekend Agenda 80s/90s Party
Sat, August 16 6:00pm - 10:00pm |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
Madkap Band
Fri, August 29 6:00pm - 10:00pm |
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Black Thorn Rose
Classic Rock, Rock |
BTR rocks Gilligan's Siesta Key!
Fri, September 5 6:00pm - 10:00pm |
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Mojo Filter
Alternative, Classic Rock, Pop, Rock |
Fri, September 19
6:00pm - 10:00pm |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
Madkap Band
Sun, September 28 6:00pm - 10:00pm |
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Black Thorn Rose
Classic Rock, Rock |
BTR rocks Gilligan's Siesta Key!
Fri, October 3 6:00pm - 10:00pm |
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Mojo Filter
Alternative, Classic Rock, Pop, Rock |
Fri, October 24
6:00pm - 10:00pm |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
Madkap Band
Fri, October 31 6:00pm - 10:00pm |
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Mojo Filter
Alternative, Classic Rock, Pop, Rock |
Fri, November 7
6:00pm - 10:00pm |
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BYNGE Fun Live NonStop Dance Rock Music
Classic Rock, High Energy Dance, Pop, Rock |
SKIPPER / LITTLE BUDDY Party @ Gilligans
Sat, November 15 6:00pm - 10:00pm $No. Cover Great Food, Cold Drinks, FREE off street parking & BYNGE |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
Madkap Band
Sat, November 22 6:00pm - 10:00pm |
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BYNGE Fun Live NonStop Dance Rock Music
Classic Rock, High Energy Dance, Pop, Rock |
HOLIDAY BYNGE PARTY on Gilligan’s Island
Fri, December 5 6:00pm - 10:00pm $FREE event, FREE off street parking, GREAT Food, Cold Drinks & BYNGE LIVE! |
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Mojo Filter
Alternative, Classic Rock, Pop, Rock |
Sat, December 27
6:00pm - 10:00pm |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
Madkap Band
Wed, December 31 6:00pm - 10:00pm |
Past Events
Artist | Date | ||
---|---|---|---|
Chris Connolly Band
Classic Rock |
June 29, 2025
6:00pm - 10:00pm $0 |
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RJ Howson
Blues, Jam Band, Rockin Blues, Southern Rock |
RJ Howson, Mike Kach, Pedro Arevalo
June 28, 2025 1:00pm - 5:00pm |
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Madkap
Classic Rock, Metal, Rock, Rockin Blues |
MadKap at Gilligans
June 28, 2025 6:00pm - 10:00pm |
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Groove This
Blues, Funk, R&B/Soul, Reggae |
Groove This! on Siesta Key!
June 22, 2025 6:00pm - 10:00pm $0 |
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Joe Bernui
Acoustic, Classic Rock, Dead, Rock |
June 18, 2025
1:00pm - 5:00pm |
