For such a small island, Cayman has an action-packed annual community social calendar. This year was a busy one. From fun runs to music events to glitzy galas, there was something for everyone in 2016. Here’s a roundup of some of the year’s notable events.


The year started off with a bang, with the Cayman Cookout at The Ritz-Carlton, Grand Cayman from Jan. 14-17. Eric Ripert, Anthony Bourdain and José Andrés were joined by other world-famous chefs, wine experts and mixologists for a weekend of demonstrations, luncheons, dinners, wine tastings and other festivities.

Next up in the “Culinary Capital of the Caribbean” was the Taste of Cayman at Camana Bay on Jan. 23 with 40 food and wine vendors.

Tonie Chisholm handed over her crown to 24-year old Monyque Brooks at the 2016 Miss Cayman Islands pageant on Jan. 30. Brooks has gone on to have a busy year representing Cayman and recently competed at Miss World in Washington, D.C. She will compete at Miss Universe early next year.

The inaugural Poinciana Festival closed out the month, showcasing local artists in music, film and visual arts, and featuring concerts, film screenings and a gala awards ceremony.


Camana Bay was the venue for the Legends at Camana Bay on Feb. 5-6. The lineup of tennis stars to play exhibition matches at Festival Green included Anna Kournikova, Jim Courier, Andy Roddick and Mark Philippoussis.

Disco Fever hit the Grand Cayman Marriott Beach Resort on Feb. 19 for the Cayman Heart Fund’s Red Dress Gala. Guests dressed either elegantly, many in red dresses, or in a ‘70s-disco theme and enjoyed dinner, a raffle, live auction and entertainment from Sea ‘N B.

Three-day festival Cayfest included the National Arts and Culture Awards Show at the Harquail Theatre, a Dress for Culture day, the Cayman Islands Folk Singers in concert, and the Red Sky at Night festival. Two-time Grammy-winning electro-jazz cellist, trombonist and composer Dana Leong performed at Red Sky at Night.


Another event which took guests back in time was the 1950s-themed Furball on March 5 at the Marriott. Hosted by the Cayman Islands Humane Society, the event is the main fundraiser for the animal shelter, which costs around US$50,000 a month to run.

Runners and walkers took to the golf course at the St. Patrick’s Day 5K around the Britannia golf course and villas on March 17. This year’s proceeds went to the Cayman Islands Cadet Corps.


NORCECA was on Seven Mile Public Beach from April 22-24 for a weekend of volleyball action. This year, 16 men’s and women’s teams from NORCECA member countries came to Cayman to spike, dig and joust their way to victory. Cayman’s team of Jessica Wolfenden and Stefania Gandolfi did the best a local team has done in this type of competition, making it to the third-place game.


Cayman’s streets vibrated to the sounds of music and revelry as feathered, glittered and scantily clad masqueraders walked, danced and jumped the Public Beach-to-George Town route of Cayman Carnival Batabano 2016. Surrounding the main adult parade were fetes featuring international artists, street parties and ample opportunity to enjoy local cuisine.

Annual comedy revue “Rundown” returned to the Harquail stage on May 12, covering topics that included politics, media, fauna and flora and religion. An extra performance date was added to raise money for the medical bills for Cayman National Cultural Foundation member George Jones.


The Flowers Sea Swim on June 11 drew competitors from all age groups and abilities for the 1-mile sea swim, 5K and 10K swims and Walk and Watch. The Flowers Group donated the US$75,000 raised at the sea swim to the Cayman Islands Cancer Society, which will enable 1,000 people to be added to the Caribbean Bone Marrow Registry.


Film fans delighted as CayFilm returned July 1-4, offering a variety of screenings, panels and discussions, and gala events. Visiting our shores this year were stars such as actress Zoe Saldana, Oscar-winning model and SFX Master Lorne Peterson, Oscar-winning sound designer Ben Burtt, and screenwriter and producer James V. Hart. The festival featured 200 films from more than 50 countries.


The 2016 Summer Olympic Games in Rio de Janeiro, Brazil, featured five Cayman athletes – hurdler Ronald Forbes, sprinter Kemar Hyman, sailor Florence Allan and swimmers Geoff and Lara Butler.


The Red Cross Dinner Dance fundraising gala on Sept. 3 featured a “Flashback to the ‘80s” theme, attracting guests in a range of retro styles. The event included an auction and raffle, three-course meal, dancing and a Madonna tribute singer.

More than 1,000 people attended the fourth annual Hannah’s Heroes Big Shave, which raised money and awareness for child cancer research. More than 100 fundraisers had their hair shaved, and the event also offered food, drink, a silent auction and balloon prize raffle.

The Cambridge American Shakespeare Tour visited the Prospect Playhouse, performing for four nights, and also ran a series of workshops and school events on island.


To some, the Breast Cancer Gala is the pinnacle of Cayman’s social events, and this year 580 people heard guest speaker Cynthia Nixon speak of her mother’s battle with the disease as well as her own. Thousands of dollars were raised for the Breast Cancer Foundation at the event’s auction, and the evening was, as usual, a roaring success.

Twenty restaurants participated in the Cayman Islands Tourism Association’s 2016 Restaurant Month, including Catch, Lobster Pot, The Bistro and Waterfront. Diners enjoyed fixed-price menus at participating restaurants for the entire month. Some restaurants offered wine pairing options. Coinciding with the final week of Restaurant Month, Cocktail Week offered a variety of cocktail-related events.


Catch Restaurant and Lounge won Restaurant of the Year, Chef of the Year and Best Ambience awards at the Jamaica Observer Table Talk Food Awards on Nov. 10. More than 400 people attended the awards ceremony at the Marriott resort, which also recognized Best Cheap Eats, Outstanding Service, Best Hidden Gem and Best Brunch, among others.

A year in Cayman wouldn’t be complete without Pirates Week. Pirates invaded all three islands during the month, arriving in Grand Cayman on Nov. 12. A week of parades, musical events, street dances, fireworks and food followed.


International storytelling festival Gimistory took place at various venues island-wide. Attendees were treated to performances from professional storytellers from all over the world, as well as from homegrown talent. The Taste of Cayman Food and Drink Festival partnered with the Cayman National Cultural Foundation to host an annual fish fry competition during the Gimistory festival.

December is always a magical time in Cayman, with Christmas events such as the Parade of Lights, the St. Ignatius Christmas Concert, HospiceCare’s Light Up a Life, and trips to see the Christmas lights in yards, roundabouts and buildings all around the island.

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