Caribbean Destinations

The Best Caribbean Islands to Visit (based on your travel preferences)

Caribbean Travel: St. Vincent

As beautiful as our coastlines may be, the Caribbean isn’t all blue water and white sand beaches. Covering 1.7 million km², comprising approximately 700 islands, and consisting of 31 countries and territories, this archipelago is overflowing with diverse experiences. Sun, sea, and sand are just the tip of the iceberg (or sandbank lol). Complex histories fostered rich cultures and varied geography gifted us with a host of intriguing outdoor activities. Indeed, each island has its own identity and distinct calling card. And it’s with this in mind that I’ve compiled a list of the best Caribbean islands to visit – based on your travel preferences.

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!

Best Caribbean Islands to visit for the Eco-Adventurer


Saba is an eco adventurer’s dream. This tiny island may only be 13 km² but it’s chocked full of stimulating outdoor activities for soft-adventure lovers. Within its borders, a towering mountain range contains over a dozen hiking trails, one of which will take you to the highest point in The Netherlands. Beneath its waters are 30 protected dive sites with some of the most stunning coral formations, diverse marine life and clearest visibility you’ll find in the Caribbean. Any nature lover could happily pass the time on this island discovering and uncovering its natural goodies. And, in case you need a little more convincing, here are some very real reasons why you should visit Saba.

Also great for: Seclusion & Solitude


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 when it comes to things to do in Grenada.

Also great for: Beaches

St. Lucia

There are many outdoor adventures to be had in St. Lucia. 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. Whether you choose to stay close to town and explore Pigeon Island close or venture into the countryside, you’re bound to encounter invigorating diversions to occupy your time!

St. Vincent

Climb to the highest point of the La Soufriere volcano and take in stunning panoramic views from 1,234 m above sea level. 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. Truth be told, St. Vincent offers no shortage of outdoor activities for a true nature lover.

Best Caribbean Islands to visit for Beach Bumming


As far as postcard-perfect beaches go, Anguilla is the Mecca. With the island’s Maundays Bay topping Conde Nast Traveler’s 2019 list of the 24 Best Beaches in the world and Forbes counting Shoal Bay among the best beaches in the Caribbean, it’s impossible to ignore the experts. Possessing sand that can best be described as “blindingly white” and water so “brilliantly blue”, you’d certainly have no problem finding the perfect stretch of coastline to while away your days on this little slice of paradise.

St. Maarten

Plane spotting at Maho Beach. Parasailing at Orient Beach. Chillaxing at Mullet Bay. Vegging out at Friar’s Bay. St. Maarten has got a strip of coastline to suit every mood and fancy. Whether you’re in the mood for big crowds or absolute seclusion, adrenaline-pumping water sports or blissful serenity, the island certainly has a beach (and beach chair) with your name on it.

Best Caribbean Islands to visit for Authenticity

Tobago Heritage Festival: Charlotteville Natural Treasures Day


Whether you’re in search of rich cultural experiences, delicious local cuisine, or unspoiled natural elements, Tobago is one of the best Caribbean islands to visit for authenticity. From the Tobago Heritage Festival to the Easter Goat Races, the island offers up Tobago-centric activities to not only entertain but educate. Take in a live African dance performance at the Pembroke Heritage Park; sample some delicious curry crab and dumpling; enjoy a dip in the island’s very own fountain of youth and truly immerse yourself in the many things that make Tobago epic.

Also great for: Eco-adventure, Beaches, History


“Bess” beaches, pumping night clubs, mountain retreats, and top-rated dining. From town to country Jamaica offers the best of both worlds to anyone with the energy to experience it all. The island is pretty massive but each region offers incredible diversions that make every 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 a delicious authentic meal? Make a pitstop at a cozy restaurant in Ocho Rios. Whatever you do, I assure you it’ll be accompanied up in that signature Jamaican charm.

Also great for: Eco-adventure, Parties, Beaches

Best Caribbean Islands to visit for Parties


Truth be told, you can visit Trinidad any time of the year and have a perfectly nice experience. But as a certified Carnival junky, I have to tell you that for anyone who loves music, can party nonstop, and enjoys carefree abandon – Trinidad’s Carnival is a MUST. The annual festival culminates in a two-day parade with tens of thousands of masqueraders decked out in gorgeous costumes. And before that comes a marathon series of fetes (parties) that begin as early as Boxing Day and end the weekend after Ash Wednesday. 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 flight, register for a costume and see what all the fuss is about. If you’re interested, here’s a step-by-step guide to Trinidad Carnival.


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 soca artistes move from one fete to the next, hyping up crowds of thousands of revellers who descend upon the island from within the region and beyond. And, if you happen to be a fan of Rihanna, chances are you’ll catch a glimpse of her as this daughter-of-the-soil is always present for the Crop Over parade!

Also great for: Beaches

Best Caribbean Islands to visit for Seclusion & Solitude


Just a hop, jump and a two-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. Sounds like your cup of tea? Check out my complete guide to Carriacou to help you plan your trip.

Also great for: Beaches

Petite Martinique

As much as I enjoyed my brief stay on Petite Martinique, I must be honest and state that it is 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. Check out this guide to Petite Martinique if you’re interested.


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.

Also great for: Beaches

When not to visit: Many establishments are closed from the end of August until mid-October so plan your trip accordingly.

Best Caribbean Island to visit for History

 Best Caribbean Islands to Visit


Cuba is a culturally rich and naturally beautiful country that has a little something to offer every traveler. What truly sets the island apart though, is its intriguing, tumultuous history. The island’s past is ever-present in the beautiful, sometimes crumbling, facades of its colonial, neoclassical and baroque architectural designs. There are volumes to uncover in the extensive, sometimes skewed, exhibits at the national museums. And around every corner, you’re likely to encounter proud and prominent reminders of the journey that led to the island’s communist existence. If you’re sold on a Cuba excursion and need some help planning your trip, check out my Cuba travel guide.

Also great for: Culture

Fact: There’s a whole world out there for you to explore. But, believe me when I say the Caribbean has something special to offer everyone – regardless of personality or preferences. So, ponder on this list of the best Caribbean islands to visit based on the type of traveler you are, I hope you’ll find one that suits your taste and make a plan to visit us in the near future.

Do you have a favorite Caribbean island? Feel free to share in the comments and say why you love it so much!

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Best Caribbean Islands to Visit    Best Caribbean Islands to Visit

(4) Comments

  1. I’ve done Anguilla, St. Maarten, and Cuba but I think Carriacou is next based on your comments!

    1. Aisha Sylvester says:

      So happy to hear that! I think you’ll love Carriacou! It’s so chill and authentic and the beaches are DIVINE!

  2. This was inspiring! A lot of these islands weren’t on my radar, but now I am looking into them. Thanks for the ideas! Which was your favorite island for diving?

    1. Aisha Sylvester says:

      Oh yay! So happy to hear that 🙂 I enjoyed diving on all of these islands but I have to say the one with the most spectacular visibility AND the most incredible encounters was Saba!

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