Cayman Live Music Weekly Run Down

The Cayman Islands Live Music Schedule is compiled using information provided by local musicians and local venues and is subject to change.

Performance times may vary, and while uncommon, some events may have an admission charge. We recommend contacting the venue directly before attending to confirm that the performance is going ahead, as weather conditions, private events, or other unforeseen circumstances may result in changes or cancellations.

Live Music Cayman: Gig Diary

Wednesday 21 October to Tuesday 27 October 2026
 

Wednesday, October 21

Dario Rivers · One GT · 5-8pm

Eugenio Leon · Tukka East End · 5.30-9pm

Michael Lemay · Westin Pool · 6-8pm

Rico Rolando · Lobster Pot · 6-9pm

Dan Ebanks · Ms. Piper’s · 6.30-9.30pm

Owen Hughes · Westin Lobby · 8-10pm

Lammy Seymour · Peppers · 8-11pm
 

Thursday, October 22

Alejandro Lemus · GT Yacht Club · 5-8pm

Musical Crew · Westin Pool · 6-8pm

Dan Ebanks · Holiday Inn · 6.30-8.30pm

Devon Edie · Union · 6.30-8.30pm

Dario Rivers · Westin Lobby · 8-10pm

Native Touch · Peppers · 8-11pm
 

Friday, October 23

James Geary · Saint June · 5.30-8.30pm

Stuart Wilson · Westin Pool · 6-8pm

Burmon Scott · Brac Reef Resort · 6-9pm

Tropical Vibez · Wyndham · 6-9pm

Daisy Lee · Union · 6.30-9.30pm

Dan & Derrick · Sunshine Suites · 7-9pm

Native Touch · Morritt’s · 7-10pm
 

Saturday, October 24

Jimmeh The Boss · Rackam’s · 4.30-6.30pm

James Geary · Saint June · 5.30-8.30pm

Dave Hennessy · Westin Pool · 6-8pm

Mariachi Cayman · Coccoloba · 6-8.30pm

Blake Hurlston · Tukka West Bay · 6-9pm

Michael Lemay · Reef Resort · 6-9pm

Stuart Wilson · Holiday Inn · 6.30-8.30pm

Jimmeh The Boss x Rion Kirk · Marriott · 7-9pm

Harmony & Luis · Abacus · 7-10pm

Daisy Lee · Westin Lobby · 8-10pm

Los Tropicanos · Peppers · 8-11pm
 

Sunday, October 25

Dan Ebanks · One GT · 4.30-7.30pm

Madam Nirosa · Union · 6.30-8.30pm
 

Monday, October 26

Nathan & Glen · Westin Pool · 6-8pm

Musical Crew · Wyndham · 6-9pm

JR Douglas · Morritt’s · 7-10pm

Dan Ebanks · Westin Lobby · 8-10pm
 

Tuesday, October 27

Caribbean Balance · Kaibo · 7-9pm

Harmony Scott · Westin Lobby · 8-10pm

Jam Night · The Bird · 9pm-12am