
EVENTS
Events
there's always something happening the Cayman Islands
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SALUD! Cayman Islands Wine Festival
Oct
18
Grand Cayman Food & DrinkOct 18 - Grand Cayman - Food & Drink -
Cayman Cocktail Week 2025
Oct
23
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Oct
30
Food & DrinkOct 23 – Oct 30, - Food & Drink -
Cayman Burger Fest
Nov
1
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Nov
22
Grand Cayman Food & DrinkNov 1 – Nov 22, - Grand Cayman - Food & Drink -
Cayman Fiesta Live - Oasis Weekend Series
Nov
7
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Nov
9
Grand Cayman Activities & EventsNov 7 – Nov 9, - Grand Cayman - Activities & Events -
Pirates Week - Grand Cayman
Nov
8
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Nov
15
Grand Cayman BeachesNov 8 – Nov 15, - Grand Cayman - Beaches -
Pirates Week - Cayman Brac
Nov
21
Cayman Brac CultureNov 21 - Cayman Brac - Culture -
Pirates Week - Little Cayman
Nov
22
Little Cayman CultureNov 22 - Little Cayman - Culture -
Cayman Islands Classic
Nov
23
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Nov
29
Grand CaymanNov 23 – Nov 29, - Grand Cayman -
Cayman Burger Fest - Grand Finale
Nov
29
Grand Cayman Food & DrinkNov 29 - Grand Cayman - Food & Drink -
Walkers Cayman Islands Marathon
Dec
7
Grand Cayman WellnessDec 7 - Grand Cayman - Wellness
Musical Events
Whether it's legendary nostalgia acts performing their greatest hits or international superstars bringing the energy, the Cayman Islands as your backdrop for an evening of electric entertainment provides unmatched experiences.
Whether it's the legendary performances from timeless nostalgia acts during the Capella Music Festival or energetic performances from international superstars to mark the beginning of Summer at the Out of This World Music Festival. there's just a different feeling when it comes to live musical performances in the Cayman Islands. Not a big concert-goer? No worries! We have weekly live music at various bars and restaurants while DJs of every genre hit the turntables at the various nightlife establishments across all three islands.
The Cayman Islands is home to some of the best entertainment in the Caribbean. No matter what your style is, we have you got your covered during you vacation in paradise. Experience the sounds of the Cayman Islands.
Carnivals
So nice, we have to do it thrice! There are three major carnivals on the Cayman Islands annual calendar. Our traditional carnival: Batabano, a party island experience on Cayman Brac with Braccanal, and the summertime extravaganza that is CayMAS Carnival.
There's a carnival for every type of reveler. Grab your friends, pack your dancing shoes, and hit the road for a carnival experience like no other when you party in the Cayman Islands.
Culinary Events
Welcome to the Cayman Islands - the Culinary Capital of the Caribbean. Experience flavorful experiences like no other.
Set your taste palettes for the rest of the year at Cayman Cookout. Indulge in amazing cocktails crafted by internationally accredited mixologists at the Cayman Islands Margarita Festival and the Cayman Islands Margarita Festival.
Is one event not enough? How about a whole month of stellar deals and specially curated menus from various restaurants across all 3 islands during Restaurant Month in October? Food, fun, and fantastic vibes go hand in hand in the Cayman Islands.
Tournaments & Sporting Events
Who says you have to leave the competitive streak at home when you're on vacation in the Cayman Islands? With several fields, soft and loamy sand, and golden sunshine no matter what time of year it is - sporting events in the Cayman Islands are like no other.
Are you an avid runner? Race in paradise during the Cayman Islands Marathon in December. How about swimming? Participate in the world renown Flowers Sea Swim, which boasts the likes of Ryan Lochte, Sharon van Rouwendaal, and Cayman's very own Brett and Shaun Fraser as past competitors.
What about eSports? Participate in the Caribbean's first ever Gaming Tournament and Technology Expo at Gamers Bay.
Aside from our major events, there are always tournaments and exhibitions happening across all three islands. We've got something for your if you're into traditional sports like cricket, basketball, football (soccer), or flag football. Or, maybe you like to take a ride on the wild side? If so, indulge in scuba diving of the coast of any of our three islands, or scale the Bluff in Cayman Brac with Rock Iguana Ltd.
Play in paradise during your next vacation.