Ticketed Events
WELCOME SHOWCASE
Thursday 14th Nov
Venue:
Harquail Theatre
1066 West Bay Road, Seven Mile Beach, Grand Cayman
Time:
7:00 pm to 10:00 pm All ages.
Visitors and locals alike will enjoy this showcase of current Caribbean and international music trends with a nod to the country music roots of the Cayman Islands.
DRUMMERS HANG
Friday 13th Feb 2026
Date:
Friday 13th February 2026
Venue:
LionFish Studios (George Town)
Time:
7:00 pm to 10:00 pm
Price:
$500 USD per person (all ages)
Featured Artists:
- Barefoot Man
- Nicolas George
- Sea N’ B
Limited capacity for 25 drum enthusiasts. Student and artist discounts available and student grant requests will be considered upon request to info@cool-out.com.
FISH TEA VIBES SHOWCASE
Wednesday 11th Feb 2026
Date:
Wednesday 11th February 2026
Venue:
Cool Out festival greens at West Bay Public Beach (in front of the Indigo Hotel)
17 Harquail Drive, George Town, Grand Cayman
Time:
Doors Open – 6:00 pm
Show start – 7:00 pm
Prices:
$100 per person
Featuring:
Local and visiting talent performing Cayman classics and new tunes of all Caribbean genres (country, SOCA, reggae, kitchen band, etc.)
All ages (children under 18 admitted free of charge with adult supervision)
Rock on the Rock
Thursday 12th February 2026
Date:
Thursday 12th February 2026
Venue:
Cool out festival greens at West Bay Public Beach (in front of the Indigo Hotel)
17 Harquail Drive, George Town, Grand Cayman
Featuring:
Local and visiting bands
Ages:
All ages, children under 18 admitted free of charge with adult supervision
Time:
Doors Open – 6:00 pm
Show start – 7:00 pm
Prices:
$100 per person
Featuring:
Local and visiting bands performing your favorite rock classics and their original music.
COOL OUT SPOTLIGHT LUNCHEON
Thursday 12th Feb 2026
Date:
Thursday 12th February 2026
Address here hide now
Venue:
Cool out festival greens at West Bay Public Beach (in front of the Indigo Hotel)
Address here hide now
Time:
Doors open at 6:00 pm
Show start at 7:00 pm
Featuring:
Local and visiting bands
All ages:
children under 18 admitted free of charge with adult supervision
Price:
$150 USD per person (all ages)
Featured Artists:
- Barefoot Man
- Nicolas George
- Sea N’ B
At this luncheon, Barefoot Man will be honored for his 50 years of creating and performing in the Cayman Islands. He will be joined for a fireside chat with legendary Nashville producer Keith Stegall. The winners of the Cool Out Songwriting Contest will be announced during this event.
GOSPEL BRUNCH
Sunday 17th Nov
Venue:
TBD
53 North Church Street, George Town, Grand Cayman
Time:
12:00 pm to 3:00 pm, All ages
Price:
TBD
$125 USD per person
Featured Artists:
- Will be announced in October
A luncheon where uplifting melodies and delicious Caribbean cuisine come together for an afternoon of live gospel performances, fellowship and great comfort food.
Free Shows
Friday 3
| 12:00 PM | |
| | | |
| 1:00 PM | |
| | | Michael Lemay (1:00-1:30pm) Madam Nirosa (1:35-2:05pm) |
| 2:00 PM | |
| | | Madam Nirosa (1:35-2:05pm) Shenna Lee (2:10-2:40pm) Matrik (Kyle Matrixx?) (2:45-3:15pm) |
| 3:00 PM | |
| | | Matrik (Kyle Matrixx?) (2:45-3:15pm) Isadora (3:20-4:50pm) BMC (4:55-5:30pm) |
| 4:00 PM | |
| | | BMC (4:55-5:30pm) |
| 5:00 PM | |
| | | DJ Sound Revolution (5:35-6:10pm) |
| 6:00 PM | |
| | | DJ Sound Revolution (5:35-6:10pm) Gordon Solomon (6:15-6:45pm) Red Boat Experience (6:50-7:20pm) |
| 7:00 PM | |
| | | Red Boat Experience (6:50-7:20pm) Patrick Lopez (7:25-7:50pm) Andy Blake (7:55-8:20pm) |
| 8:00 PM | |
| | | Andy Blake (7:55-8:20pm) Georgie Duarte (8:25-8:55pm) |
| 9:00 PM | |
| | | Core Band (9:00-9:45pm) Stuart Wilson (9:50-10:40pm) |
| 10:00 PM | |
| | | Stuart Wilson (9:50-10:40pm) Xosia (10:45-11:15pm) |
| 11:00 PM | |
| | | Xosia (10:45-11:15pm) Erica Assai (11:20-12:10pm) |
| 12:00 PM | |
| | | Erica Assai (11:20-12:10pm) |
| 1:00 AM |
Saturday 4
| 12:00 PM | |
| | | Dexter Bodden (12:30-1:00pm) |
| 1:00 PM | |
| | | Jimmeh the Boss (1:05-1:30pm) Bob Moseley (1:35-2:05pm) |
| 2:00 PM | |
| | | Bob Moseley (1:35-2:05pm) SugarDaddi (2:10-2:40pm) Chuck & Barrie (2:50-3:25pm) |
| 3:00 PM | |
| | | Chuck & Barrie (2:50-3:25pm) Beneil Miller & Band (3:30-4:10pm) |
| 4:00 PM | |
| | | Beneil Miller & Band (3:30-4:10pm) DJ Super C (4:15-4:50pm) |
| 5:00 PM | |
| | | Ben Hud (5:00-5:40pm) Clever Knots (5:50-6:20pm) |
| 6:00 PM | |
| | | Clever Knots (5:50-6:20pm) TaCaTaC (6:30-7:00pm) |
| 7:00 PM |
COOL OUT LONE STAR JAM SESSIONS
Thursday, Friday, Saturday
Venue:
Lone Star Bar & Grill
688 West Bay Road, Seven Mile Beach, Grand Cayman
Time:
10:00 pm to Close
Price:
Free
When the most talent artists of Cool Out come together to share their talents, magic happens. You never know which GRAMMY™ winning visiting artist may show up to play alongside local legends at these jam sessions of incomparable talent. True music afficionados will not want to miss this.
COOL OUT BUSKERS’ CORNER AT LOCO
Thursday, Friday & Saturday
Venue:
LOCO mexican cantina Camana Bay, Seven Mile Beach, Grand Cayman
Time:
4:00 pm to 7:00 pm on Thursday
5:00 m to 10:00 pm on Friday
11:00 am to 1:00 pm on Saturday
Price:
Free
Located in Cayman’s most popular outdoor mall and business area, the Open Canvas stage at Karoo offers an eclectic mix of mainstream entertainment suitable for families, shoppers and anyone enjoying great food and drinks in this modern Caribbean atmosphere. Live music performances by local and visiting artists will be featured alongside visual artists, dancers and other forms of creative expression. This stage is hosted by Cameron Douglas, a visual artist and entrepreneur known for The Duppy Project and the Open Canvas initiative.
Thursday 2
| 12:00 PM | |
| | | |
| 1:00 PM | |
| | | |
| 2:00 PM | |
| | | |
| 3:00 PM | |
| | | |
| 4:00 PM | |
| | | |
| 5:00 PM | |
| | | Carlosvgarcia Fine Art Gallery (5-6pm) |
| 6:00 PM | |
| | | Harmony Scott (6-7pm) |
| 7:00 PM | |
| | | *Wide Awake (7-9pm) |
| 8:00 PM | |
| | | *Wide Awake (7-9pm) *kirk Salsa King Dance (8-9pm) |
| 9:00 PM | |
| | | *Kirk Salsa King DJ (9-10pm) |
| 10:00 PM |
Friday 3
| 12:00 PM | |
| | | |
| 1:00 PM | |
| | | |
| 2:00 PM | |
| | | |
| 3:00 PM | |
| | | |
| 4:00 PM | |
| | | Carlosvgarcia Fine Art Gallery (4-5pm) |
| 5:00 PM | |
| | | *Takewando Nathan (5-6pm) |
| 6:00 PM | |
| | | *Max (6-7pm) |
| 7:00 PM | |
| | | *Dario Rivers (7-8pm) |
| 8:00 PM | |
| | | *Quintisential (8-9pm) |
| 9:00 PM | |
| | | *Jardel DJ close (9-10pm) |
| 10:00 PM |
Saturday 4
| 12:00 PM | |
| | | *Taekwondo (12-1pm) |
| 1:00 PM | |
| | | *Jimmeh La Pierre (1-2pm) |
| 2:00 PM | |
| | | Taekwondo (2-3pm) |
| 3:00 PM | |
| | | Dance (3-4pm) |
| 4:00 PM | |
| | | *Cayman Tings (4-5pm) |
| 5:00 PM | |
| | | *Carlosvgarcia Fine Art Gallery (5-6pm) |
| 6:00 PM | |
| | | *Spoken Word (6-7pm) |
| 7:00 PM | |
| | | *SK3 Tara (7-8pm) |
| 8:00 PM | |
| | | Sand kickers (8-9pm) |
| 9:00 PM |
COOL OUT AT BONNY MOON BEACH CLUB
Thursday, Friday, Saturday
Venue:
Bonny Moon Beach Club
53 Seabath Lane, Seven Mile Beach, West Bay, Grand Cayman
Time:
8:00 pm to midnight
Price:
Free(VIP table seating available for purchase)
COOL OUT AT MS. PIPER’S
Friday & Saturday
Venue:
Ms. Piper’s Kitchen & Garden
22 Piper Way Seven Mile Beach, Grand Cayman
Time:
5:00 pm to 9:30 pm
Price:
Free
This hidden gem located at the mid-point of Seven Mile Beach is best kept secret for both locals and visitors who enjoy the beauty of the tropical setting along with delicious Caribbean inspired cuisine. Cayman’s best kept secret is about to become one of Cool Out favorite stages for those who like to groove to the sweet vibes while enjoying the tranquil atmosphere. Hosted by the sensational crooner James Geary, this stage will feature local R&B, soul and pop performances of local artists all with a Caribbean twist.