3 Quick and Easy Caribbean Escapes for Your Next Winter Getaway


Grey skies are gonna clear up… We’ve picked our top destinations for all the escapists, adventure–seekers and families dreaming of a winter getaway to the Caribbean.

Close your eyes and remember your last winter escape… that sense of serenity you feel as you take off, leaving the flurries behind – then landing in a place where ice can only be found floating in your glass.

We are sun–seeking creatures by nature, and when the skies stay grey for days at a time, many of us start dreaming up an escape plan. The dilemma: Which sun–soaked, white–sand beach to choose? We’ve whittled your options down to three sure–to–deliver destinations perfect for whatever type of getaway you need most.

November 17, 2020

Get away from it all in

Andros, Bahamas

An aerial view of Kamalame Cay in the Bahamas
A bird’s–eye view of tropical paradise: Kamalame Cay is a family–run private island with 20 secluded, bougainvillea–draped bungalows, cottages, beach houses and villas.   Photo: The Great House of Kamalame Cay

This 5,957–square–kilometre island is home to five national parks, more than 60 known species of flourishing orchids and 175–plus “blue hole” underwater caves just waiting to be explored. Locals refer to the collection of cays that make up Andros as the “Big Yard” – and it really is a natural playground, seemingly designed with the winter–weary traveller in mind. Plus, the largest of the Bahamas’ Out Islands is one of the least developed, with a population of just 8,000, making it a great choice for Covid–19–era travel.

Palmtree lined walkways at the Caerula Mar Club in Andros, Bahamas
   Photo: Caerula Mar Club


  • Caerula Mar Club — Canadian HGTV stars Bryan and Sarah Baeumler renovated this boutique resort on South Andros for their show Island of Bryan. The secluded collection of 18 suites and six villas, which landed a spot on Condé Nast Traveler’s 2020 Hot List, includes dedicated yoga and meditation areas to complement the get–away–from–it–all island vibe. Kayaks, stand–up paddleboards and bicycles let you explore on your own, while local Caribbean ingredients mix with international flavours at the three on–site restaurants, culminating in dishes like red–curry conch soup and fresh–caught hogfish.

The bar at the Great House of Kamalame Cay
   Photo: The Great House of Kamalame Cay


  • Seafood lovers, rejoice: The so–called “Land of Crabs” doesn’t disappoint. The Great House at Kamalame Cay offers Asian–influenced Bahamian dishes like Andros stone crab with wasabi mayo, or try the fresh conch at F&H Takeaway on the Lowe Sound waterfront.

Two people fishing on a speedboat in Andros, Bahamas
   Photo: The Bahamas Ministry of Tourism & Aviation of Andros


  • Start with a meditative hike through Rockland Pine Forest for a chance to spot the migratory Kirtland’s warbler mingling with various tropical birds, or shop for souvenirs in Andros Town, where local artisans sell the island’s namesake Androsia batik fabric. Snorkellers, swimmers and divers will revel in the 305–kilometre–long barrier reef – part of the third–largest reef system in the world (behind only Australia and Belize); shipwrecks and reef sharks are common sightings. The season for bonefish (a catch–and–release sport fish) runs from October through February, while mahi mahi, grouper and snapper are among the catches most favoured by fishermen and diners alike.

Feel the beat in

Port Antonio, Jamaica

Icah Wilmot tests the waters at Orange Bay in Jamaica
Renowned local musician Icah Wilmot tests the waters at Orange Bay, a small bay between Buff Bay and Port Antonio, perfect for a day of sun and surf.   Photo: Oumayma B. Tanfous

Jamaica has been a guaranteed good time for as long as the island has welcomed tourists – and 2020 hasn’t changed that. Port Antonio offers a quieter experience away from Ocho Rios and Kingston, while still keeping you close enough to explore them (about a two–hour drive to each). The area is a proven retreat: 007 author Ian Fleming bought 15 acres here and settled in to write every winter. The next James Bond movie, No Time to Die, was partially filmed in the area, so expect some movie trivia alongside your reggae vibes and rum punch.

A cream and brown toned suite at the Geejam resort in Jamaica
   Photo: Jamaica Tourist Board


  • Geejam — For music lovers, the splashy Geejam resort recently unveiled a dozen new 550–square–foot rooms called Rhumba Studios – each one with sweeping views of the rainforest and the sea. Guests (keep an eye open for Drake or Gwen Stefani) have access to the on–site recording studio.

  • Goldeneye — Ian Fleming wrote more than a dozen novels on the island, and his estate (you can sleep in his villa, where his writing desk remains) is part of this resort of the same name. A collection of elegant villas, cottages and beach huts are set far enough apart in the jungle to offer privacy for outdoor showers and evening dips in the lagoon.

A seafood platter at Chris's Cook Shop in Port Antonio, Jamaica
   Photo: Bobby Salinas


  • Authentic Jamaican cuisine is easy to find on the streets of Port Antonio. Anthony Bourdain raved about the oxtail and curry goat at the roadside Chris’s Cook Shop, but any local can point you to a spot best suited to whatever you’re craving, whether it’s a Steel Bottom cocktail of beer and rum at Dr. Hoe Rum Bar or jerk chicken at Piggy’s Jerk Center.

A group of people swimming beside Reach Falls in Jamaica


  • This region’s mix of mountain scenery, lush junglescape and emerald waters has plenty to offer outdoor explorers. At Reach Falls, swim in a natural pool under a waterfall or jump through the “Rabbit Hole” into the scenic swimming hole below. Historic Folly Ruins is Instagram perfection, and reclining on a river raft as a local guide transports you along the Rio Grande remains a grand outing.

Kick back with the kids in

Cayo Guillermo, Cuba

A blue and white boardwalk leading to the beaches of Playa Pilar in Cuba
The shimmering white sand (perfect for sinking your toes into) and warm turquoise waters of Playa Pilar make it one of Cayo Guillermo’s – and Cuba’s – most beautiful beaches.   Photo: Juan-Rojas

One of five main cays that make up the Jardines del Rey (King’s Gardens) archipelago on the northern coast of Cuba, Cayo Guillermo is an overlooked beach lovers’ paradise. White–sand beaches abound, and the calm, shallow turquoise water makes it great for families with young kids. Whether you’re a morning stroller or an afternoon lounger, there’s plenty of sand to go around.

The long rectangular pool at the Cayo Guillermo Resort Kempinski in Cuba


  • Cayo Guillermo Resort Kempinski — Go soon and you’ll likely be among the first to enjoy the five–star luxury resort property, which opened its doors in March only to close them again when the pandemic took hold. Now set to reopen this month, expect a serene hideaway on the edge of the cay that’ll make you feel like you’re standing on the edge of the world. The property’s more than 200 rooms include everything from adjoining family–room options to six overwater, panoramic–view villas (each with a private pool).

Fresh lobster caught for the beach bars and grills of Cuba


  • Search out the ranchons (beach bars and grills) scattered across Cayo Guillermo and neighbouring Cayo Coco: Ranchon Cuba Libre is renowned for its lobster dinners. Need a nightcap? The Hemingway Cigar Bar & Lounge pairs two famous Cuban exports (rum and cigars) with one of its famous residents (Ernest Hemingway’s The Old Man and the Sea is set here).

Kitesurfing on the waters of Cayo Guillermo in Cuba


  • Cayo Guillermo’s best feature is its beaches. Activity–seekers can choose from kitesurfing, stand–up paddleboarding and snorkelling, while divers will delight in exploring the miles of vibrant coral reef just offshore. The beaches, especially Playa Pilar at the cay’s northwestern end, are a paradise of shallow, warm waters, soft sand and rentable umbrellas – the perfect place to spend a sunny afternoon.