Cayman Islands Festivals and Events

Active Caribbean Travels to the Cayman Islands

The 2019 Festivities of the Cayman Islands

2019 Cayman Islands Festival & Events Calendar:

  • The Cayman Cookout is January 16 to 20 on Grand Cayman’s Seven Mile Beach – The 5 day event features celebrity chefs, cooking demonstrations, tastings, tours, dinners, Food & Drink pairings and unique epicurean experiences.
  • The Taste of Cayman is January 26 at Camana Bay, Grand Cayman. This Food and Drink Festival is held at a number of local restaurants.
  • KAABOO, a Music, Art, Comedy and Culinary extravaganza. This overwhelming event is being held February 15 & 16 on Grand Cayman’s Seven Mile Beach. This year’s musical line-up includes Duran Duran, Chainsmokers, Bryan Adams, Counting Crows, Flo Rida, Zedd, Maxi Priest, Jason Derulo, Blondie, LIVE, Magic!, Sean Paul, Shaggy, Blues Traveler and more (although it’s hard to believe!). If that wasn’t enough, comedy headliners include Norm Macdonald, Wanda Sykes, Kevin Nealon and Tom Green!
  • Cayman Carnival Batabano happens in May along the west coast of Grand Cayman, featuring street parades with music, dance and colourful costumes for adults and children.  Local food vendors will also be there. This year’s schedule includes:
    • Beach J’Ouvert on April 20 (new for 2019)
    • Le Masque Ball May 2
    • Friday Night Fete May 3
    • Carnival / Parade, as well as a Food Festival and ‘Last Lap fete’ all happen on May 4 – This is a big day!
    • Junior Batabano Street Parade & Family Fun Day on May 11
  • The CayMas Carnival, a celebration of Caribbean Culture takes place from May 16 to 20
  • Flowers Sea Swim, benefiting the Cayman Islands Crisis Centre, takes place June 15 – 17 and includes a One Mile Sea Swim and 5k & 10k Sea Swims. There’s over $100,000 in cash and prizes up for grabs.
  • The island also hosts the 2019 UANA Masters Open Water Swimming Championships with delegations from the Americas, from June 15 to 18.
  • Cayman Cocktail Week usually takes place in October, with a number of fun and interactive events
  • The annual Cayman Islands Pirates Week Festival is held in November. The Caribbean’s premier pirates festival is also the Cayman Islands’ largest national event covering Grand Cayman, Cayman Brac and Little Cayman. Events include parades, costume contests, scavenger hunts, street parties, and boat races.

Also of note, the Cayman Islands International Fishing Tournament will be held May 2 – 5, while the Cayman Billfish Rundown will happen May 14 – 17.

The Cayman Islands Triathlon typically takes place every November. The Cayman Islands Marathon will be held on December 8. The event consists of a full marathon, half marathon, 4-person relay and a Kids Fun Run, all along the glorious Caribbean sea.

Also check out other Things To Do while visiting the Cayman Islands

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