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: October 14–20, 2026

WEDNESDAY, OCT 14

Dario Rivers · One GT · 5–8PM

Jimmeh The Boss · Jacks · 5:30–7:30PM

Eugenio Leon · Tukka East End · 5:30–9PM

Michael Lemay · Westin Pool · 6–8PM

Chris Sanchez · Marriott · 6–9PM

Hi-Tide · Ms. Piper’s · 6:30–9:30PM

Dan Ebanks · Westin Lobby · 8–10PM

Lammy Seymour · Peppers · 8–11PM

THURSDAY, OCT 15

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, OCT 16

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

Musical Crew · Sunshine Suites · 7–9PM

Native Touch · Morritt’s · 7–10PM

Hi-Tide · Westin Lobby · 8–10PM

Dan Ebanks · Ms. Piper’s · TBC

SATURDAY, OCT 17

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

Harmony Scott · Holiday Inn · 6:30–8:30PM

Jimmeh The Boss x Rion Kirk · Marriott · 7–9PM

Dan & Derrick · Abacus · 7–10PM

Daisy Lee · Westin Lobby · 8–10PM

Los Tropicanos · Peppers · 8–11PM

SUNDAY, OCT 18

- Madam Nirosa · Union · 6:30–8:30PM

MONDAY, OCT 19

Nathan & Glen · Westin Pool · 6–8PM

Musical Crew · Wyndham · 6–9PM

JR Douglas · Morritt’s · 7–10PM

Dan Ebanks · Westin Lobby · 8–10PM

TUESDAY, OCT 20

Caribbean Balance · Kaibo · 7–9PM

Harmony Scott · Westin Lobby · 8–10PM

Jam Night · The Bird · 9PM–12AMTuesday, 13 October