With literally hundreds of thousands of destinations to consider, how do you decide where to invest your time, money, and energy? Call me biased (because I am, just a little) but I highly recommend dedicating some of your vacation days to exploring the Caribbean. The archipelago offers hundreds of islands from which you can choose so there’s bound to be at least one that suits your needs. That being said, I’ve compiled a list of the top Caribbean islands you need to visit at least once in your lifetime.
NB: This is based on my own travel experiences so feel free to research beyond these options to find an island that’s just right for you!
For the Experiential Travellers
Whether you’re in search of rich cultural experiences, delicious local cuisine, or unspoiled natural elements, Tobago is THE Caribbean island to visit. I won’t pretend that I’m not biased toward this gem of an island I recently called home but I’m also being honest. From the Tobago Heritage Festival to the unique curry crab and dumpling, secluded beaches to a rainforest with over 200 species of birds, I promise you will have a ton of fun immersing yourselves in the many experiences Tobago has to offer.
Special times to visit:
⁃ If Culture is your thing, you definitely need to experience the Tobago Heritage Festival which takes place the last 2 weeks in July, ending on Emancipation Day, August 1.
⁃ If you’re a foodie, then get yourself to Tobago for the annual Blue Food Festival which will take place on the third Sunday in October.
“Bess” beaches, pumping night clubs, mountain retreats and top rate dining…from town to country Jamaica offers the best of both worlds to any traveller with the energy to experience it all. As far as Caribbean islands go, Jamaica is pretty massive in size but each of the island’s various regions offer rich experiences that make the hours-long drive worth it. In the mood to stroll on a white-sand beach? Spend some time in MoBay. Want to float peacefully along a river? Hire a bamboo raft in Portland. Looking for vibrant nightlife? Schedule some time for club hopping in Kingston.
For the Partying Travellers
Truth be told, you can visit Trinidad anytime of the year and have a perfectly nice experience. But as a certified Carnival junky I have to tell you that anyone who loves music, can party nonstop, and enjoys carefree abandon, Trinidad for Carnival is THE island to be. The annual festival is marked by a two day parade for masqueraders decked out in gorgeous costumes, as well as a marathon series of fetes or parties that begin as early as Boxing Day and end the weekend after the big parade. Trust me, Carnival is not for the faint of heart (or the light of wallet) but if you have the stamina and the funds to experience it, book a last minute flight, find yourself a costume in fineahband.com and see what all the fuss it about.
Special time to visit: The Carnival parade takes place on the Monday and Tuesday before Ash Wednesday.
While Trinidad’s Carnival will always top my list, Barbados’ annual Crop Over festival is another highly-rated Carnival in the Caribbean. Massive parties with ample vibes span a series of days. Scores of regional soca artistes move from one fete to the next, hyping up the crowds filled with thousands of revellers who descend upon the island from within the region and beyond. And, if you happen to be a fan of super-star Rihanna, chances are you’ll catch a glimpse of her as this daughter of the soil never missed a Crop Over parade!
For the Eco-Adventurers
Love venturing off the beaten path and don’t mind getting a little dirty? Grenada is for you! Whether you’re scuba diving the underwater sculpture garden, hashing through the Grand Etang Forest Reserve or getting a therapeutic massage from one of the island’s many waterfalls, you’re going to be spoiled for choice if you decide to visit this island in 2019.
Hike to the top of a Piton or scuba dive the reef just a few miles off its base. Soak up natural minerals at the sulphur springs then follow it up with a therapeutic massage from a beautiful waterfall. There are many outdoor adventures to be had in St. Lucia, whether you choose to explore Pigeon Island close to the town of venture into the countryside, you’re bound to encounter a diversion that’s well worth the trip!
Climb to the highest point of La Soufriere volcano and take in stunning panoramic views from. Road trip to the northern village of Owia to soak in the natural salt ponds. And climb several hundred steps to the top of Fort Duvenette. There’s more to vacationing than beach-bumming when you’re on this little rock. St. Vincent offers no shortage of outdoor activities for a true nature lover to indulge in while visiting this Caribbean island.
For the Off-the-Grid Travellers
Just a hop, jump and a 2 hour boat ride from Grenada, Carriacou is exactly what you envision when you think “off the grid Caribbean escape”. Just 440 km², this island paradise has a population of 8,000 and boasts some of the best beaches I’ve ever encountered in the Caribbean. It’s the ideal spot for vacationers who want to enjoy uncrowded stretches of coastline, unbothered by locals or throngs of other visitors.
As much as I enjoyed my brief stay on Petit Martinique, I must be honest and state that is it not an island I can recommend to many. This little dot with a population of 900 will appeal only to super low-key, low-budget travellers who want nothing more than to fall completely off the grid. No internet. No bathing beaches. No nightlife. No shopping. No joke. With less than a handful of restaurants (with unpredictable hours of operation) and a couple of guest houses, PM is where you go to truly unplug. However, the locals are friendly, the scenery is beautiful and it offers a rare and peaceful retreat you’re unlikely to find on any other inhabited Caribbean island.
With a population of just over 4,000, Bequia is definitely an island where you can go to maximize your downtime. Limited people translates into unlimited peace with beautiful beaches for you to just kick back and soak up the sun. Quaint vending stalls and cozy restaurants line the main street, as well as the waterfront, so you’ll have your pick of options when it comes to shopping and dining.
When not to visit: Many establishments are closed from end of August until mid-October so you may want to plan your trip accordingly.
For The History Buffs
Cuba is a culturally rich and naturally beautiful country that has a little something to offer every traveler. What truly stands out to me however, is its intriguing, tumultuous history. It’s alive and evident in the beautiful architecture that lines the streets of Old Havana, the extensive (if not skewed) exhibitions at the Museo de Revolucion, the massive grounds of the fort, El Morro and so many other reminders of the island’s communist existence.
Of course, this list in no way covers the full length and breadth of the incredible destinations that exist within the Caribbean region. In fact, it doesn’t even cover all of the islands I’ve visited and loved. These are simply the islands that I believe deliver enriching experiences that will add an interesting dynamic to your travel plans. It is my sincerest hope that you will indeed venture across to our little archipelago next year and explore to your heart’s content. Whether you end up on one of the rocks I’ve suggested or another one altogether, the Caribbean community will be happy to host you!