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
17
May
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...
13
Jun
Recommended
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
Recommended
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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New Years Eve
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January
February
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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...
8
May
Charity
Inclusive Happy Hour
🌈 Inclusive Kids Happy Hour – Let’s Move & Have Fun! 🌈 Join Island Spirit Cayman for our Inclusive Kids Happy Hour, designed to get children active while supporting body...
8
May
Charity
Inclusive Kids Chill Out Zone
🌿 Inclusive Kids Chill-Out Zone 🌿 Join Island Spirit Cayman for our Inclusive Kids Chill-Out Zone, a calming space designed to help children unwind, regulate, and reconnect through gentle practices....
