Explore Cayman For a better experience on Explore Cayman, Update your browser.

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.


16th-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.

26th January - 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.


3rd February - Super Bowl 2019

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.

21st February - 11th March - 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

24th February - 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 2019

2nd March - Red Sky at Night Festival

An enchanting evening, rich in arts and culture. Live performances, music and great food. www.artscayman.org.

6th March - 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.

15th 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.

30th-31st 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 2019

Easter 2019

You’ll find lots of fantastic events happening over Easter in the Cayman Islands. This year Easter falls on Sunday 21st April. Good Friday and Easter Monday are public holidays so residents enjoy a lovely long weekend in Cayman.

10th-11th April - Batabano Carnival Junior Parade

Featuring children’s parades, calypso and soca dancing, steel drums and food.

22nd April - Kaibo Kitefest

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

25th April-12th May - 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

30th April-7th 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 2019

4th 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 2019

15th 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 2019

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.


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.

25th-31st October - Cayman Cocktail Week

A unique celebration of Cayman's cocktail culture with an incredible array of cocktail parties, culinary events and tastings.


3rd 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.

7th-11th  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.

16th  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.

30th Nov -7st Dec - 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


7th December - Cayman 27'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.

8th 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.


 Tuesday, 1 January  New Year’s Day (observed)
 Monday, 28 January  National Heroes Day
 Wednesday, 6 March  Ash Wednesday
 Friday, 19 April  Good Friday
 Monday, 22 April  Easter Monday
 Monday, 20 May  Discovery Day
 Monday, 10 June  Queen's Birthday
 Monday, 1 July  Constitution Day
 Monday, 11 November  Remembrance Day
 Wednesday, 25 December  Christmas Day
 Thursday, 26 December  Boxing Day