Cayman Islands Events Calendar
Discover the ultimate 2026 Cayman Islands event calendar! Explore top festivals, live music, culinary events, cultural celebrations, and more. Whether you’re in Grand Cayman, Cayman Brac or Little Cayman, stay updated with daily listings on EventPro for the best events happening in the Cayman Islands.
FEATURED
7
Jun
Charity
Run & Walk for Shankar
Join us for a 4K Run or Walk in support of Shankar Lingam, our beloved colleague from Hotel Indigo and Kimpton Seafire, who has been hospitalized for over nine months...
12
Jun
Daylight And Radiance
Join the Cayman National Choir and Orchestra for an uplifting evening of music celebrating light, joy, and the vibrant energy of summer. Daylight and Radiance brings together a dazzling mix...
13
Jun
Food & Drink
Gin Fest Cayman Islands
World Gin Day · Saturday, June 13, 2026 An Elevated Evening of Gin,Cocktails & Discovery Gin Fest Cayman Islands is a premium, experience-led celebration of gin, cocktails, and elevated hospitality...
27
Jun
Food & Drink
Margarita Masters Season 2
Margarita Masters returns to the Cayman Islands for Season 2 — bringing together top bartenders for an electrifying cocktail competition set in the heart of Camana Bay at THE ISLAND....
3
Jul
25
Jul
Food & Drink
Cayman Islands Margarita Festival
Five years ago, we set out to create something the Cayman Islands had never seen — a celebration of craft margaritas, incredible food, and world-class music under the island sky....
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1
Jan
Cayman Motoring Federation Membership
Cayman Motoring Federation (CMF) is established for the purpose of enhancing the motoring movement and safeguard interests in relation to motoring in the Cayman Islands through education, training and special...
17
May
Culturama – Show 2
Round two, let’s go! Culturama keeps the excitement going on Sunday, May 17 at the F.J. Harquail Theatre. Showtime is 6:00 p.m., and you can expect another burst of stunning...
22
May
Charity
Kiwanis Breakfast for Dinner
The Kiwanis Club of Grand Caymans primary fundraiser this year is our ‘Breakfast for Dinner’ on Friday, May 22nd. The evening will be held at Mykonos Steak Club and will...
