Adventurers of the Caribbean

These three islands are beckoning you for a winter escape….

By Felicity, World Traveler

Felicity—a 20-something travel lover—has teamed up with her friends from around the world to provide readers with local, insider knowledge of today’s most awe-inspiring destinations. Through writing, photography, and video, they’ll share the best tricks and tips for experiencing a place authentically and getting off the beaten path.

Three men diving off a waterfall with a green forest behindImage: Shutterstock

Winter is a cozy time filled with festivities and snowy slopes and hands wrapped around mugs. But winter in the northern hemisphere can also be crazy-making; too often it feels as though the sun sets directly after lunch, and who really wants to leave the house (/accomplish anything at all) after it’s dark out? 

Fortunately, all that’s between you and the sun your body craves is a flight to our wonderful, warm friends in the south! And if, like me, you prefer to attain your vitamin D by combining luxuriously chill beach time with off-the-beaten-path adventure, there are three Caribbean islands that are especially ideal for you:

A girl in shorts standing on a raft on a river in the jungleImage: Shutterstock


Featuring big, dramatic landscapes and an even bigger personality, Jamaica is a truly colorful jewel in the Caribbean. Despite its relatively small size, the cultural impact it’s had on the world is remarkable; it's famously given us Bob Marley, Usain Bolt, the newly crowned Miss Universe, and so much more. You may know about reggae, but there are endless other parts of Jamaica to be explored.

After your first big nap on one of the country's beautiful beaches (as all good holidays should begin), take in views of the island’s vibrant coral reefs with a snorkel or scuba tank. Then, for a different but equally fun experience on the water, hop aboard one of the catamarans heading to Floyd’s Pelican Bar. Set about a mile off Jamaica’s southwest shore, this bar literally sits on stilts in the middle of the ocean, with a boardwalk you can dangle your legs off of while enjoying a Red Stripe.

A bar on stilts in the middle of an ocean with turquoise coloured waterImage: Shutterstock

Then it’s into the water for a swim around the bar, since you’ll need to work up an appetite for one of their lobster or fish dishes.

A man swimming in bright blue water

With its red soil, disappearing streams, caves, waterfalls, and verdant mountains, the ‘off-beach’ parts of Jamaica are also a paradise for outdoors-y types. Go caving, take a hike (or three!) in the Blue Mountains, and go rafting down the Martha Brae River. This latter activity is particularly great if you want to be outside doing something, but that ‘something’ is lounging…

A man using a pole to push a raft down a jungle riverImage: Shutterstock

In Jamaica’s capital city of Kingston, the Bob Marley Museum is an absolute must, and if you’re into old buildings with witchy legends, Rose Hall should be paid a visit, too. Located northwest of Montego Bay, Jamaica’s greatest—and most instagrammable—old house was completed in 1770; it’s now a museum and tours are hosted regularly, during which you’ll hear the  intriguing tale of the White Witch of Rose Hall.

A large white and brick colonial manor with a grand staircaseImage: Shutterstock


Looking for a super low-key escape? Tobago, the lesser known (and less developed) island of the “Trinidad and Tobago” pairing, is perfect for you. Just 25 miles long by 9 miles wide, it's the kind of easygoing and friendly place where you can still find a deserted beach to hang out on.

A point of white sand covered in palm trees extending into water at sunsetImage: Shutterstock

With the Atlantic lapping its western shore and the Caribbean Sea to the east, Tobago's brilliantly colorful reefs are some of the best in the Caribbean. This makes it an ideal destination for those looking to scuba dive (or learn how to), or if you want to paddle out from shore and enjoy some excellent snorkelling in crystal-clear waters.

Fish swimming underneath the water above a reef of orange coralImage: Shutterstock

From Pigeon Point Heritage Park, hire a glass-bottomed boat to tour around Buccoo Reef, a spectacular marine park. Be sure to stop and have a swim around Nylon Pool, a three foot deep natural pool with a bright white sandy bottom.

A shallow area of turquoise water with a bottom of wide sand and clouds overheadImage: Shutterstock

Like Jamaica, you’ll also find adventure on Tobago when you head inland. The island’s central ridge of mountains shelter the Forest Reserve, the western hemisphere’s oldest protected rainforest. Hire a guide to point out some of the forest’s bounty of fruit, herbs, and spices, and end your hike at the idyllic Argyle Falls with its natural rock pools.

A rocky waterfall surrounded by green forestImage: Shutterstock

For the avid ornithologists, this is also your place. The island’s abundance of trees and cliffs mean a diverse population of birds make Tobago their home. I’m not really even into birdwatching, but who wouldn’t want to spot a flock of these scarlet ibis?!

Bright red birds fly in a flock over waterImage: Shutterstock

A final major perk of Tobago: instead of navigating a maze of bland dishes designed to suit tourist's tastebuds,  you can easily get tasty and authentic local food. Think flavorful Caribbean fare like spicy crab stew, fresh grilled fish, juicy kebabs, goat curry, and a moreish snack of fried bread topped with stewed chickpeas called “doubles.”

A person holding street food of fried dough with chickpeas and green sauceImage: Shutterstock


Grenada is another Caribbean island that manages to fly relatively low under the radar. This aptly nicknamed “Spice Island” has a distinct culture and intensely rich history, meaning there’ll be no shortage of fascinating sites amongst this natural paradise to explore.

A colourful colonial town on the Caribbean island of GrenadaImage: Shutterstock

Let’s start with my favorite thing (perhaps ever) to do, and one of the reasons why Grenada is beloved: swimming.

A natural swimming pool with clear water and  a small waterfallImage: Shutterstock

This island is replete with outstanding beaches (45, in fact) and countless secluded coves. Most famous of the beaches is Grand Anse, but be sure to try others like Bathway Beach and Petite Anse. For those truly dedicated to literally finding paradise, hop on a ferry for the short ride to the small neighboring island of Carriacou. After a (slightly rough) taxi ride down some backroads, you’ll arrive at Paradise Beach which, as you can see, lives up to its name. If you’re willing to work a bit for it, you can find a white and turquoise slice of perfection that’s free from the hordes of tourists. 

A tropical beach with a white sandy beach, turquoise water, and green treesImage: Shutterstock

For the food-lover, Grenada can also provide a serious culinary education. Learn about famous homegrown spices like nutmeg, cocoa, and cinnamon, and try flavors potentially foreign to your tongue like tamarind, soursop, sea moss, and golden apple.

Another of Grenada’s draws is a remarkable underwater sculpture park in the Molinere Beauséjour Marine Protected Area off the island’s west coast. First constructed in 2006, the sculptures—some of which weigh as much as 15 tons—were eco-consciously built from concrete and rebar.

Underwater sculpture of children holding hands in a circleImage: Shutterstock

These haunting and powerful works in part pay tribute to the two million African slaves who lost their lives crossing the Atlantic; they were also designed with the intention to improve the health of the local ecosystem, providing homes to marine life and aiding in the restoration of coral reefs damaged in several intense hurricanes. 

A person scuba diving near an underwater statue of JesusImage: Shutterstock

A beach in Jamaica with a wind sailing board on it

Jamaica Inn

Main St/Old Rd 1, Ocho Rios, Jamaica

  • Complimentary Continental breakfast for two daily (in room)
  • Property will offer upgrade upon availability at time of check-in
  • High-Speed/Enhanced Wi-Fi
White chairs and tables on a deck with a pool overlooking the ocean

S Hotel Jamaica

7 Jimmy Cliff Boulevard, Montego Bay, Jamaica

  • 100 USD Spa credit
  • Complimentary Buffet breakfast for two daily
  • Early check-in upon availability
  • Late check-out upon availability
  • Property will offer upgrade upon availability at time of check-in
  • High-Speed/Enhanced Wi-Fi
An empty hammock on a beach in the Caribbean

Calabash Luxury Boutique Hotel and Spa

Beach Lane, St George, Grenada

  • Complimentary daily full breakfast for two
  • Early check-in upon availability
  • Late check-out upon availability
  • Property will offer upgrade upon availability at time of check-in
  • High-Speed/Enhanced Wi-Fi

Inspired to visit the Caribbean? Connect with one of our expert travel agents.