Annual Events

Check out our interactive Events Calendar! It features all the best events in Cayman in an easy to use calendar format.

There are always plenty of fun events and activities happening in the Cayman Islands to keep visitors and residents entertained. From delicious foodie events and sporting spectaculars to community happenings and a variety of magical Cayman Christmas and New Year's Eve events; there really is a Cayman event to suit everyone's tastes. Cayman events are always sociable occasions that generate a great turnout and are a wonderful opportunity to spend time with old friends and meet new ones.

You can find a list of all the major events and public holidays below, however check out our events calendar for lots more great events happening in Cayman.

JANUARY 2020

15th-20th January – Cayman Cookout
Join Chef Eric Ripert for the annual Cayman Cookout, celebrating food and wine. Enjoy demonstrations from world famous chefs, competitions, tastings, gala dinners and more at The Ritz-Carlton, Grand Cayman.

FEBRUARY 2020

2nd February - Super Bowl 2020
Whether you're an NFL fan or your interest in Sunday Night Football begins and ends with the food, the Super Bowl always makes for a great evening - and the half time entertainment is not to be missed! Check out our article on the Best Places to Watch the Super Bowl in Cayman.

26th February - Agricultural Show
A fun family event in Lower Valley, showcasing the Island’s best animals, produce and food with live music, arts and crafts sale and activities for all the family to enjoy.

29th February - Red Sky at Night Festival
An enchanting evening, rich in arts and culture. Live performances, music and great food. www.artscayman.org.

Dates TBC - Cayfest
An arts festival showcasing local talent. An eclectic mix of visual arts, music, theatre, film screenings and fashion design. Performances are held across the Cayman Islands. www.artscayman.org

Date TBC - Off The Beaten Track (OTBT)
The OTBT race is the only off road 50KM ultra marathon based in Cayman. Designed to mimic the gruelling Marathon des Sables, the 26.2 mile course covers off-road trails and cuts across beaches, the bush and back roads of Grand Cayman. Run as an individual or as part of a relay team. Proceeds are donated to both local charities and two international charities: Crossing Borders and Facing Africa. www.offthebeatentrack.ky.

MARCH 2020

17th March - St Patrick’s Day 5k Irish Jog  
The annual Irish Jog. With a bit of Irish luck you could win some great spot prizes including sunset sails, restaurant vouchers, spa services and more. For more information, please contact Rebecca Ebanks on (345) 815 7797 or email IrishJog@butterfieldgroup.com.

Saturday 21 March - LIVE Street Food Festival
Offering an eclectic selection of street food from around the world and around the way. Join LIVE Street Food Festival for a world of taste with street food from your favourite chefs, food trucks and restaurants.

28th-29th March - The Cayman Islands Orchid Show
A fantastic floral show that includes indigenous Cayman orchids with exotic orchids for sale. Held at the Queen Elizabeth II Botanic Park. 9am-4.30pm. www.facebook.com/QEIIbotanicpark.

April 2020

Easter 2020
You’ll find lots of fantastic events happening over Easter in the Cayman Islands. This year Easter falls on Sunday 12th April. Good Friday and Easter Monday are public holidays so residents enjoy a lovely long weekend in Cayman.

4th April- Taste of Cayman Food & Drink Festival
A food and wine festival that showcases over 45 of Cayman’s best restaurants and attracts over 5,000 people. Enjoy live entertainment, music and fireworks. This is a highlight of the year and demonstrates Caymanian culture at its best. Click here for more details.

13th April - Kaibo Kitefest
A family fun day on the beach with kite competitions, live music and kite-making for the kids. www.kaibo.ky

30th April-3rd May - Cayman Islands International Fishing Tournament
Anglers compete annually in this much anticipated event. Register early by contacting (345) 945 3131 or visit www.fishcayman.com.

MAY 2020

2nd May - Batabano Carnival Junior Parade
Featuring children’s parades, calypso and soca dancing, steel drums and food.

9th May - Batabano Adult Parade
An explosion of Caribbean music, dancing and costumes that brings George Town to life with steel pan bands, floats and a parade. www.caymancarnival.com.

JUNE 2020

13^th June - Flowers Sea Swim
Over 1,000 competitors, including Olympic level swimmers, take part in this annual one mile swim along Seven Mile Beach. Hundreds of prizes to be won. www.flowersseaswim.com.

JULY 2020

July-Aug - Summer Moonlight & Movies
Every Tuesday throughout July-Aug enjoy a family friendly movie under the stars in Camana Bay. Bring a blanket and have a picnic!

1st July - Constitution Day
Celebrate Constitution Day at Camana Bay Harbour.

OCTOBER 2020

1st-31st October - Cayman Restaurant Month
If you’ve always wanted to try a particular restaurant in Cayman or love to dine out but your budget doesn’t allow you as many nights out as you’d like, Cayman Restaurant Month is your chance to re-visit your favourite restaurant or branch out and try something new.

Dates TBC October - Cayman Cocktail Week
A unique celebration of Cayman's cocktail culture with an incredible array of cocktail parties, culinary events and tastings.

NOVEMBER 2020

8th November - The Cayman Islands Triathlon
Held on the first weekend in November. All you need to enter is a bathing suit, a bicycle, helmet and running shoes! Race solo or as part of a team. There are also participant training sessions prior to the main event which are well attended and great fun www.triathlon.ky.

5^th-9th  November - Pirates Week
A swashbuckling good time for all three Islands! The week features a full-on mock pirate invasion of the Island and capture of the Governor! The festivities continue for five fun-filled days of pirate parades, music, street dancing, competitions, wonderful local food and drink, kids day, sports events, Heritage Days and firework displays. www.piratesweekfestival.com.

12th Novemebr-29th November - Rundown
An annual comedy show that has been running for 27 years. It takes a light hearted dig at the multicultural society that is Cayman. www.artscayman.org

19th  November - Annual Christmas Tree Lighting
A giant Christmas tree decorated with thousands of fairy lights is switched on at Camana Bay by Santa himself. Enjoy the carol singing and the Christmas market.

27th November - 5th December - Gimistory
An international festival that brings together storytellers from Cayman, the Caribbean and North America. Events take place in parks, beaches and even private backyards, evoking an atmosphere of the days of yore when storytelling was the only entertainment. www.artscayman.org

DECEMBER 2020

5th December - Cayman National's Parade of Lights
Join an evening of celebration as beautifully lit up boats sail into the harbour in Camana Bay. Enjoy food, drink, a Christmas market, live music and a fireworks display. 6pm-8pm.

6th December - Cayman Islands Marathon
Full and half marathons, four person relays and a kid’s fun run with the beautiful scenic backdrop of the Island and Caribbean Sea. www.caymanislandsmarathon.com.

25th December - Christmas Day
Christmas is always a fun-filled day in Cayman with numerous restaurants hosting Christmas lunch. Keep an eye on the calendar as more details are added!

31st December - New Year’s Eve Fireworks
Ring in the new year with displays all along Seven Mile Beach; there is also a formal display at 8pm over The Harbour at Camana Bay. Visit the event calendar for a full list of New Year's Eve Events in Cayman.

CAYMAN ISLANDS PUBLIC HOLIDAYS 2020