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Luxury Villa Travel in the New Year

Travel Tips |

In the blink of an eye, 2019 has come to a close. It was a year of memorable moments on Cayman—a royal visit by Prince Charles and Duchess Camilla, world-class events boasting gourmet farm-to-table cuisine and the excitement of expanding our luxury portfolio.

Luxury Cayman Villas was thrilled to help families celebrate buccaneering lore, dance along with Batabano’s masquerade bands and kick back to appreciate the good life on Grand Cayman. And, we welcomed singer-songwriter Cloe Wilde and the music legends of BET’s reality series “Ladies’ Night” to indulge in the unrivaled luxury at our “Evolution” villa. It was a year of unforgettable experiences, a year of flavors and a year of joyous celebrations under the sun.  

As we cap off Cayman’s holiday season with New Year revelry, we are thankful for the many blessings of 2019 and are excited to share what’s coming to Grand Cayman in 2020.

Cayman’s Holiday Traditions 

The festive season in the Cayman Islands is filled with special events and traditions celebrated with a Cayman twist. From craft markets and cookies to dazzling parades and Santa Claus, you’ll find a holiday calendar brimming with magical experiences. 

  • Annual Christmas Tree Lighting: Watch as a 40-foot Christmas tree lights up the night at Camana Bay. Add in gently falling artificial snow, a brilliant fireworks display, and a host of musicians, entertainers and craft stalls, and your family is sure to have a dreamy holiday experience.
  • Parade of Lights: The Harbour transforms into an enchanting setting as a procession of bedazzled boats cruise to a soundtrack of festive carols. Live entertainment, fireworks and colorful holiday markets cap off the magical evening.  
  • Santa Sightings: Children will thrill to visits by both Traditional Santa, dressed to impress in his proper red-and-white Santa suit, and Caribbean Santa adorned in tropical flair.
  • Christmas Lights: Private homes throughout Cayman provide a fairy-tale holiday setting with twinkling lights, nativity scenes and Christmas-themed spectacles. Join one of the Christmas Lights tours operated by the National Trust or drive around to take in the sights at your own pace.
  • Christmas Movies, Music & Theater: Cuddle up al fresco with your loved ones for a family-friendly Christmas movie shown on a big screen under the stars. Theater lovers can indulge in a night of Tchaikovsky and ballet at The Nutcracker or take in a holiday performance at the Prospect Playhouse.
  • Christmas Brunch: Visitors can completely relax and hand over the kitchen responsibilities on Christmas Day. Many restaurants and hotels offer lavish brunch buffets or set menus with plenty of free-flowing bubbles.
  • Holiday Races & Fun Runs: The Jingle Bell Walk/Run, Intertrust Marathon, Santa Run and Dashing Thru the Sand events are popular family-friendly social affairs that support great causes. Join one of the activities or gather to cheer on the participants.
  • New Year’s Eve: Toast to the New Year with a cache of events designed to suit revelers of all ages. Dance on the beach, attend an elegant black-tie event or simply chill on the sand for a magnificent fireworks display at midnight. 
  • Shop Local: Support local artisans and pick up handmade jewelry, ornaments and crafts—or that last-minute gift—at the Pink Ladies Christmas Bazaar, the Visual Arts Society Christmas Craft Market or the Camana Bay’s Farmers & Artisans Market. 

Cayman Islands’ Events in 2020

Whether you’re anticipating delicious Cayman cuisine or long for a weekend getaway in 2020, you’ll want to mark your calendars with these not-to-be-missed occasions.

  • Cayman Cookout, January 15-20, 2020: Noted as one of the world’s most prestigious food and wine events, Grand Cayman’s annual culinary extravaganza is a multi-day festival showcasing sublime feasts and events hosted by internationally acclaimed chefs. It’s a bon vivant experience you won’t find anywhere else!
  • Taste Of Cayman, April 4, 2020: Sample foods and beverages from Cayman’s favorite restaurants, plus enjoy kitchen demonstrations, mixologist competitions and live entertainment.
  • Easter, April 12, 2020: Both Good Friday and Easter Monday are public holidays, and the long weekend offers events and activities for all ages. Camp along the beach, indulge in Easter brunch or participate in the age-old practice of kite flying.
  • Batabano, May 9, 2020: As one of Cayman’s most entertaining events, Batabano delights spectators and participants with eye-popping costumes, choreography, incredible floats and engaging music. Junior Batabano (beginning on May 2) welcomes kids and families to join the celebration in a safe, family-oriented way. 
  • Flowers Sea Swim, June 15, 2020: Cheer on participants racing along Seven Mile Beach, or join the competition for a bit of splashy Caribbean fun.
  • Queen’s Birthday, June 15, 2020: Held annually in George Town to honor the British heritage of the Cayman Islands, Her Majesty’s birthday celebration features a full military parade and a garden reception at the Government House.
  • Constitution Day, July 6, 2020: Kick off July with barbecues, fireworks and kid-friendly entertainment to commemorate three national holidays: Canada Day, American Independence Day and Cayman’s Constitution Day. 
  • Cayman Restaurant Month, October 2020: Grand Cayman’s premier culinary event highlights Cayman’s best restaurants with special prix fixe menus. Cayman Cocktail Week caps off the delicious month of flavors!
  • Pirates Week Festival, November 5-9, 2020: Each November, this one-of-a-kind event offers an electrifying variety of street dances, fireworks, a treasure hunt, a mock pirate invasion, parades and Heritage Days.

New Beginnings on Grand Cayman

Ringing in the New Year is a time to anticipate the new beginnings and new opportunities that the year will bring. Could 2020 be the year you master the perfect getaway? A holiday where you spend sun-drenched afternoons with your favorite book … where your little one learns to swim in your private infinity pool … or where your family discovers the underwater world of Stingray City?

If you’re new to private villa stays, we invite you to book your 2020 vacation and get ready to be impressed! A villa holiday gives you all of the freedom, convenience and luxurious comforts you’re dreaming of coupled with the privacy and security the most discerning travelers have come to expect. From the moment you arrive, our top-notch amenities and services provided by our expert team allow you to slip seamlessly into the blissful rhythm of the islands. 

As we celebrate the beginning of a new year, we are truly thankful for the opportunities to deliver unforgettable family holidays throughout 2019. We will continue to raise the stakes in luxury travel in 2020 and look forward to creating authentic luxury travel experiences that become enduring memories for our guests—like you! We can’t wait to welcome you to Grand Cayman in 2020!

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