COOL OUT SUNSETS & SONGS
Thursday 2nd Nov
Venue:
Ritz Carlton Grand Cayman
1066 West Bay Road, Seven Mile Beach, Grand Cayman
Time:
6:00 pm to 10:00 pm
Prices:
- Heroes – $4,500 USD per table of 10
- All the Fun– $4,000 USD per table of 10
- Somewhere in the Caribbean – $3,000 USD per table of 10
Featured Artist:
- Paul Overstreet
Immerse yourself in an extraordinary and unique experience at Cool Out Sunsets & Songs, hosted by the vivacious and energetic Jessica Bodden of Bloom Consulting, renowned for her exclusive, elegant and unforgettable events. This will be a night that the most discerning aficionados of food and country music will absolutely adore. This listening event is unlike any other, featuring the extraordinary talents of GRAMMY™ winning singer-songwriter Paul Overstreet and the secrets behind his songs! Prepare yourself for an evening of sophistication, where extraordinary talent, culinary excellence and an intimate setting combine to create an experience that is truly magical. Join us at the Ritz Carlton ballroom transformed into the Caribbean’s most exclusive speakeasy and let the magic of music unfold.


COOL OUT WATERFRONT
Thursday 2nd Nov
Venue:
Seven Mile Beach Corridor.
Venue disclosed on Ticket Confirmation.
Time:
6:00 pm to 12:00 am
Prices:
- Rockstar Box – $25,000 USD (maximum 10 people) includes F&B package, bottle service, private bar, elevated box area, front of stage viewing area, designated entrance and Cool Out light stick fan for each guest.
- Superfans – $550 USD per person includes a private bar, front of stage viewing area, designated entrance and Cool Out light stick fan.
- General Admission – $350 USD per person (Pre-sale $250 USD per person)
Featured Artists:
- Steve Aoki
- Jason JG Gilbert
- Elyse Saunders
- Nicholas George
- Nire Bird
- AleXa
- Jimmeh The Boss
For the first time in Cayman, legendary producer and DJ Steve Aoki will headline this showcase of visiting and local talent as an exclusive “after party” to the Cool Out Conference, the location of which is only revealed to those who are lucky enough to purchase tickets.
COOL OUT NASHUP
Saturday 4th Nov
Venue:
Cayman Cabana
53 North Church Street, George Town, Grand Cayman
Time:
8:00 pm to 12:00 am
Price:
$125 USD per person (18+ ID required)
Featured Artists:
- Nash Overstreet
- Jason JG Gilbert
- DJ Steven King
- DJ CLiFF
- Nire Bird

The hottest local and visiting DJs led by Nash Overstreet and Jason JG Gilbert will mash up the latest hits and old favorites under the stars where guests will be able to dance the night away by the sea.
COOL OUT FISH TEA VIBES
Saturday 4th Nov
Venue:
F.J. Harquail Cultural Centre
17 Harquail Drive, George Town, Grand Cayman
Time:
6:00 pm to 10:00 pm
Prices:
- Orchestra (Rows A through D) – $150 USD per seat includes Cool Out light stick fan
- Orchestra (Rows E through Q) – $80 USD per seat
- Mezzanine & Balcony – $60 USD per seat
Featured Artists:
- Pebble Stone
- Red Boat Experience
- Swanky Kitchen Band
The Korean Wave will hit the historical Cayman opry house for the first time with the performance of Korean based traditional band Pebble Stone. Red Boat Experience will then take guests on a journey into the rich heritage of Caribbean culture. The evening will be topped off by the infectious melodies, lively twangs and vibrant sounds of the beloved Swanky Kitchen Band. Prepare to dance and have your heart captured by the mix of traditional Korean and Caribbean cultures.
COOL OUT CABANA
Thursday 2nd, Friday 3rd, Saturday 4th Nov
Venue:
Cayman Cabana
53 North Church Street, George Town, Grand Cayman
Time:
Thursday 2nd – 12:00 pm to 10:00 pm
Friday 3rd – 12:00 pm to 10:00 pm
Saturday 4th – 12:00 pm to 7:00 pm
Price:
Free
Co-hosted by none other than the Cayman soca legend himself Brent McLean and the illustrious Cabana owner Luigi Moxam, this stage is set to ignite the dance floor with the irresistible beats of soca, reggae and other captivating Caribbean genres. Join us at Cabana for spectacular ocean views and vibrant performances by local aspiring talent from across the Caribbean.
Line ups soon to come.

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 OPEN CANVAS
Thursday 2nd Nov, Friday 3rd Nov, Saturday 4th Nov
Venue:
Karoo
Crescent at Camana Bay, Seven Mile Beach, Grand Cayman
Time:
Thursday 2nd – 5:00 pm to 10:00 pm
Friday 3rd – 5:00 pm to 10:00 pm
Saturday 4nd – 12:00 pm to 10:00 pm
Price:
Free
Hosted by the fabulously creative Douglas Cameron (aka “JR”), this stage is where talents will collide, showcasing an eclectic mix of musicians, artists, dancers and athletes from Western and Korean genres that will cater to families of all ages. From mesmerizing acoustic sets to Kpop or even foot tapping jazz, there’s something for everyone to enjoy. Bring your entire family along and let the Cool Out Open Canvas Stage be your playground of imagination and inspiration.
Line ups soon to come.
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 LONE STAR
Thursday 2nd, Friday 3rd, Saturday 4th Nov
Venue:
Lone Star Bar & Grill
688 West Bay Road, Seven Mile Beach, Grand Cayman
Time:
Thursday 2nd – 4:00 pm to 10:00 pm
Friday 3rd – 12:00 pm to 10:00 pm
Saturday 4th – 12:00 pm to 10:00 pm
Price:
Free
Gather your friends and family and head over to this iconic and much beloved establishment on Seven Mile Beach where the sweet melodies and infectious rhythms will transport you to a world where country meets pop, Caribbean meets rock’n’roll and everyone is guaranteed to have a blast. You never know what star might make a surprise appearance on stage. Get ready to dance, sing-along and create memories that will last a lifetime.
Line ups soon to come.

Thursday 2
12:00 PM | |
| | Kharim (12:00-1:00pm) |
1:00 PM | |
| | Laura Dixon (1-2pm) |
2:00 PM | |
| | Jason Isaacs (2-3pm) |
3:00 PM | |
| | Daisy Lee (3-4pm) |
4:00 PM | |
| | Hannah (4-5pm) |
5:00 PM | |
| | Hedge Fund (5-6pm) |
6:00 PM | |
| | Hedge Fund (6-7pm) |
7:00 PM | |
| | Hedge Fund (7-8pm) |
8:00 PM | |
| | Cayman tings (8-9pm) |
9:00 PM | |
| | Tacacatac (9-10pm) |
10:00 PM |
Friday 3
12:00 PM | |
| | |
1:00 PM | |
| | |
2:00 PM | |
| | |
3:00 PM | |
| | Alejandro Lemus (3-4pm) |
4:00 PM | |
| | Jimmeh Da boss (4-5pm) |
5:00 PM | |
| | Harmony Scott (5-6pm) |
6:00 PM | |
| | |
7:00 PM | |
| | *Martina Jackson (7-8pm) |
8:00 PM | |
| | Rico Rolando (8-9pm) |
9:00 PM | |
| | TaCaTaC (9-10pm) |
10:00 PM |
Saturday 4
12:00 PM | |
| | Cool OUt Karaoke (12-1pm) |
1:00 PM | |
| | |
2:00 PM | |
| | Chambria Dalhouse (2-3pm) |
3:00 PM | |
| | Rebecca Milne (3-4pm) |
4:00 PM | |
| | Brent McLean (4-5pm) |
5:00 PM | |
| | Yoan Tamayo (5-6pm) |
6:00 PM | |
| | |
7:00 PM | |
| | |
8:00 PM | |
| | BoB |
9:00 PM | |
| | BoB |
10:00 PM |

COOL OUT AT THE HIVE
Thursday 2nd Nov, Friday 3rd Nov, Saturday 4th Nov
Venue:
The Hive
Canal Point Drive, Grand Gayman
Time:
Thursday 2nd – 5:00 pm to 11:00 pm followed by DJ until 1:00 am
Friday 3rd – 5:00 pm to 12:00 am followed by DJ until 2:00 am
Saturday 4th – 5:00 pm to 9:00 pm followed by DJ until 12:00 am
Price:
Free
Featured Artists:
- Hot Chelle Rae featuring special guest Rico Rolando
- SaintAir
- River Town Saints with special guest Nicholas George
- LionFish
Nestled in the heart of the seven mile beach corridor, Cool Out at The Hive will take you on a thrilling music journey in one of the hottest new bars on island. Pop sensations Hot Chelle Rae whose infectious hits will have you singing to every beat will headline this impressive group of visiting and local bands. Get ready to stomp your boots and experience the magic as River Town Saints, Saint Air, LionFish and others who will be hiting the stage to showcase their original songs and old favorites. Expect some surprise collabs with Rico Rolando and Nicholas George and you never know who else will make a surprise appearance on stage. This stage is sure to please not only the lovers of classic rock but also those who are seeking out the next big thing.
Line ups soon to come.
Thursday 2
5:00 PM | |
| | Ticketed Event |
6:00 PM | |
| | Ticketed Event |
7:00 PM | |
| | Ticketed Event |
8:00 PM | |
| | Ticketed Event |
9:00 PM | |
| | Ticketed Event |
10:00 PM | |
| | Ticketed Event |
11:00 PM | |
| | Ticketed Event |
12:00 PM | |
| | Ticketed Event |
1:00 AM |
Friday 3
5:00 PM | |
| | |
6:00 PM | |
| | Stuart Wilson (6:00pm – 7:00pm) |
7:00 PM | |
| | LionFish (7:00pm – 7:30pm) River Town Saints ft Nicholas George (7:30pm – 8:30pm) |
8:00 PM | |
| | River Town Saints ft Nicholas George (7:30pm – 8:30pm) Saintair (8:30pm – 9:30pm) |
9:00 PM | |
| | Saintair (8:30pm – 9:30pm) |
10:00 PM | |
| | Hot Chelle Rae ft Rico Rolando (10:00pm – 11:00pm) |
11:00 PM | |
| | House DJ 11pm onward |
12:00 PM |
Saturday 4
5:00 PM | |
| | Core Band – Julia Meyerhoff (5-7pm) |
6:00 PM | |
| | Core Band – Julia Meyerhoff (5-7pm) |
7:00 PM | |
| | Another Band TBD (7:30-8:30pm) |
8:00 PM | |
| | Another Band TBD (7:30-8:30pm) |
9:00 PM | |
| | Red Room with DJ JMess – Jason Rankin (9pm-12am) |
10:00 PM | |
| | Red Room with DJ JMess – Jason Rankin (9pm-12am) |
11:00 PM | |
| | Red Room with DJ JMess – Jason Rankin (9pm-12am) |
12:00 PM |
COOL OUT RUM POINT
Friday 3rd, Saturday 4th Nov
Venue:
Rum Point Club
North Side, Grand Cayman
Time:
Friday 3rd – 12:00 pm to 2:00 pm
Saturday 4th – 12:00 pm to 7:00 pm
Price:
Free
We cannot wait for everyone to enjoy the most idyllic venue within the Cool Out repertoire of satellite stages. Situated on the North East coast of Grand Cayman, Rum Points offers the most beautiful views of the North Sound and during Cool Out, it will offer some of the sweetest melodies performed by local and visiting artists to go along with the view. Treat yourself to an island favorite mudslide and local delicacies while putting your toes in the sand and soaking up the sea breezes. Just a short boat ride from seven mile beach to Rum Point and you will be on your way to an entirely different world of tranquility, great food and fabulous live music.
Line ups soon come.
Friday 3
12:00 PM | |
| | |
1:00 PM | |
| | Stuart Wilson (1:00-2:00pm) |
2:00 PM |
Saturday 4
12:00 PM | |
| | |
1:00 PM | |
| | |
2:00 PM | |
| | |
3:00 PM | |
| | |
4:00 PM | |
| | |
5:00 PM | |
| | |
6:00 PM | |
| | Maric |
7:00 PM |

COOL OUT GOSPEL – POSTPONED
Sunday 5th Nov
Venue:
Cayman Cabana
53 North Church Street, George Town, Grand Cayman
Time:
11:00 am to 2:00 pm
Price:
$125 USD per person
Hosted by Cabana’s very own Luigi Moxam, guests of this very special gospel brunch will indulge in a delightful celebration of gospel music and mouthwatering local cuisine with views to match overlooking the harbor. Let the harmonious tunes and delectable dishes nourish your soul as you gather with loved ones in an atmosphere of faith and togetherness. Don’t miss this opportunity to unite your love for gospel music with incredible culinary offerings of the Caribbean for an unforgettable afternoon of blessings, good food and unforgettable memories.
COOL OUT SPOTLIGHT – BAREFOOT MAN – POSTPONED
Friday 3rd Nov
Venue:
Ritz Carlton Grand Cayman
1066 West Bay Road, Seven Mile Beach, Grand Cayman
Time:
12:00 pm to 3:00 pm
Price:
$150 USD per person (all ages)
Featured Artists:
- Barefoot Man
- Nicolas George
- Sea N’ B
Join us as we shine the spotlight on a true Caribbean legend . At this year’s Cool Out Spotlight, we will pay tribute to the local musical icon Barefoot Man (George Nowak). We will help George celebrate his 50th anniversary of creating and performing in the Cayman Islands. From his beloved collaborations with renowned performers like Andy Martin, Sea n’B, to his prolific songwriting, Barefoot’s has left an indelible mark in Cayman and abroad with his funny, eclectic and groundbreaking style. Experience an afternoon of pure talent and delicious cuisine carefully put together by the very special host Nicholas George, known to Barefoot as his son Nick. Whether you are a dedicated Footie or new to Barefoot’s enchanting sound, the Cool Out Spotlight event is an opportunity for everyone to revel in the unique and timeless music of Barefoot Man.