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Events on Grand Cayman, and Luxury Villa Rentals for Festivals

November 2016 Grand Cayman Events

Pirates Week: November 12 - 22

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 eleven fun-filled days of pirate parades, music, street dancing, competitions, wonderful local food and drink, kids day, sports events, Heritage Days and firework displays.

Annual Christmas Tree Lighting: November 21

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.

National Catboat Championship: (Dates TBA)

A series of exciting catboat races. Sailors compete in the hope of being named the Camana Bay National Catboat Champion.

Gimistory: November 28 - December 5

The Cayman Islands International Storytelling Festival, which brings people together from around the world. There is plenty of entertainment and entry is free.

December 2016 Grand Cayman Events

Cayman 27's Parade of Lights: December 6

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.

New Year's Eve Fireworks: December 31

Ring in 2017 with displays all along Seven Mile Beach; there is also a formal display at 8pm over The Harbour at Camana Bay.

January 2017 Grand Cayman Events

Cayman Cookout: January 15 - January 18

A weekend of food and wine demonstrations from world famous chefs, competitions, dinners and more in Grand Cayman. There are over 34 events happening over the weekend.

February 2017 Grand Cayman Events

Taste of Cayman Food & Wine Festival 2016: (Date TBA)

A food and wine festival that showcases over 40 of Cayman's best restaurants and attracts over 500 people. The event turns 25 this year and is a must for foodies.

Moonlight & Movies: Valentine's Edition: February 10 - February 12

Bring a blanket and picnic for a special Valentine's edition of Moonlight & Movies in Gardinia Court.

Agricultural Show: February 18

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.

Mardi Gras Festival on the Waterfront in George Town: February 18

Catch some beads, get your face painted, enjoy live music and join in the revelry! The party kicks off at midday and is free to enter.

The Cayman Islands Orchid Show: February 28 - March 1

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.

March 2017 Grand Cayman Events

St Patrick's Day Music on The Paseo: March 17

Celebrate St. Patrick's Day with a performance by Grand Cayman's only Irish band, Twisted Clover. Enjoy traditional Irish songs, jigs and reels from Irish rock bands.

April 2017 Grand Cayman Events

3rd - 6th Easter Events at the Ritz-Carlton: April

The Ritz-Carlton holds several fun events over the Easter weekend including an Easter Bunny Tea that children love and a Taittinger Champagne Easter Brunch where adults can enjoy bottomless champagne. Visit The Ritz-Carlton Grand Cayman website for more details.

Kaibo Kitefest: April 6

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

TBC Annual Cayman Catboat Easter Regatta: Easter Weekend

Local maritime and holiday traditions will meet over the Easter Weekend, as the Cayman Catboat Club gears up for the 8th Annual Cayman Catboat Easter Regatta, taking place on Easter Saturday at Tiki Beach. Easter campers on Seven Mile Beach - and the wider community are invited to watch this exciting, traditional event as local sailors head out for a day of competition on the water. The races will take place from 12pm-4pm.

Batabano Carnival Junior Parade: April 25

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

Cayman Islands Fashion Week: (Dates TBA)

Cayman Islands Fashion Week serves as a platform for showcasing international, Regional and local trend setting fashion designers. The show also features models from some of the world's top agencies including Ford, Major, DNA, RED, Muse, Next, IMG and Elite. Sessilee Lopez, Georgie Badiel, Kacie Schaffer and Bobby Roache are amongst the diverse selection of top models that have strutted our runways.

May 2017 Grand Cayman Events

Batabano Adult Parade: May 2

An explosion of Caribbean music, dancing and costumes that brings George Town to life with steel pan bands, floats and a parade.

June 2017 Grand Cayman Events

Flowers Sea Swim<: June 13

Over 800 competitors, including Olympic level swimmers, take part in this annual one-mile swim along Seven Mile Beach. Hundreds of prizes to be won.

July 2017 Grand Cayman Events

Constitution Day Fireworks: July 6

A spectacular display for families at Camana Bay.

October 2017 Grand Cayman Events

Cayman Restaurant Month: October 1 - October 31

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 2014 is your chance to re-visit your favorite restaurant or branch out and try something new.

Cayman Cocktail Week: Late October

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

Halloween Spooktacular: October 31

Trick or treat around Camana Bay. Take part in Halloween crafts, watch a Spooky Create Features and more.

Villa CM WS1, Grand Cayman, Seven Mile Beach, 1 bedrooms, 1 bathrooms, WiFi, WIMCO Villas

CM WS1

Ideal for avid snorkelers, ground-floor apartment with beautiful ocean views, steps from the water

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1 br / 1 ba

Villa CM COR, Grand Cayman, Seven Mile Beach, 7 bedrooms, 7 bathrooms, WiFi, WIMCO Villas

CM COR

Spacious and private, panoramic water views, steps from the sand, walk to eateries, bars, and shops

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7 br / 7 ba

Villa CM DIS, Grand Cayman, Seven Mile Beach, 2 bedrooms, 2 bathrooms, WiFi, WIMCO Villas

CM DIS

Second-floor apartment, steps from beach, spacious living area, screened balcony overlooks the sea

Seven Mile Beach, Grand Cayman
2 br / 2 ba

Villa CM HAL, Grand Cayman, Cayman Kai, 2 bedrooms, 2 bathrooms, WiFi, WIMCO Villas

CM HAL

Nestled at end of a cove, cheerfully decorated cottage, private boat dock, steps from the beach

Cayman Kai, Grand Cayman
2 br / 2 ba

Villa CM HAL, Grand Cayman, Cayman Kai, 2 bedrooms, 2 bathrooms, WiFi, WIMCO Villas

CM HAL

Nestled at end of a cove, cheerfully decorated cottage, private boat dock, steps from the beach

Cayman Kai, Grand Cayman
2 br / 2 ba

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WIMCO Villas, CM WS1, Grand Cayman, Seven Mile Beach, 1 bedrooms, 1 bathrooms

CM WS1

Ideal for avid snorkelers, ground-floor apartment with beautiful ocean views, steps from the water

Seven Mile Beach, Grand Cayman
1 br / 1 ba

WIMCO Villas, CM COR, Grand Cayman, Seven Mile Beach, 7 bedrooms, 7 bathrooms

CM COR

Spacious and private, panoramic water views, steps from the sand, walk to eateries, bars, and shops

Seven Mile Beach, Grand Cayman
7 br / 7 ba

WIMCO Villas, CM HAL, Grand Cayman, Cayman Kai, 2 bedrooms, 2 bathrooms

CM HAL

Nestled at end of a cove, cheerfully decorated cottage, private boat dock, steps from the beach

Cayman Kai, Grand Cayman
2 br / 2 ba

WIMCO Villas, CM HAL, Grand Cayman, Cayman Kai, 2 bedrooms, 2 bathrooms

CM HAL

Nestled at end of a cove, cheerfully decorated cottage, private boat dock, steps from the beach

Cayman Kai, Grand Cayman
2 br / 2 ba

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WIMCO Villas and Hotels, Hotel, Ritz Carlton - Grand Cayman, Grand Cayman, Book now with WIMCO

Ritz Carlton - Grand Cayman

Spanning 144 acres on Seven Miile Beach, the Ritz-Carlton, Grand Cayman features a Greg Norman designed golf course, La Prairie Spa and a gourmet Gastronomic restaurant by Eric Ripert.

Grand Cayman

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