A Beginner’s Guide To the Caribbean Islands

Whether you just want to bar hop and show off your salsa moves in Old San Juan, stray farther afield to surf the waves in legendary Rincón, snorkel the crystalline waters of the island of Vieques, or explore tropical rainforest El Yunque, Puerto Rico is full of enchanting escapades.

Once you're all partied out, take a break from San Juan’s urban buzz for an after-dark LED kayak excursion around Condado Lagoon. And for one of Puerto Rico’s most rewarding experiences on the water, sail off on a catamaran day trip from Fajardo to the island of Culebra, where snorkeling through pristine coral reefs and sipping piña coladas will be the only things on your to-do list.

From the rolling and mist-shrouded coffee farm landscapes of the Blue Mountains to Jamaica’s resort-lined north coast, the Caribbean’s third-largest island delivers beaches and culture (think: jerked foods, reggae lore, and more) in equal parts, making it the ideal destination for a road trip.

Try horseback riding and ziplining near Montego Bay, and take the time to detour into Jamaica’s lush interior for ATV adventures through rugged landscapes and river rafting along the Great River—two epic activities you can cram in during a single day’s fun. Of course, don’t miss the sand and waterfalls in spots such as Ocho Rios and Negril.

With nearly 700 islands, the Bahamas ticks some of the requisite Caribbean boxes (even though it’s not in the Caribbean Sea) with impossibly powder-fine coral sand beaches and transparent waters. And if you’ve always dreamed of snorkeling with pigs, Pig Beach on the island of Exumas is the place to do it.

Sample conch fritters and sip rum punch on a food tour in Nassau, the tropical capital, before admiring graceful green sea turtles during boat trips to Green Cay. The marine life in the Bahamas is unmatched—and the best part is you can dive into most of it with just a snorkel, mask, and fins.

Although it’s not quite within the official Caribbean territory, Turks and Caicos is hard to discount from this list, thanks to its postcard-perfect sapphire waters lapping upon sugar-white sands. Picture you and your partner toasting to the sunset while surrounded by sparkling waters on a romantic, adults-only catamaran cruise.

Or, head out by boat in Grace Bay to snorkel among clouds of reef fish before picnicking on an uninhabited stretch of sand at Little Water Cay (Iguana Island). Finally, let your vacation memories live on with a drone photo shoot while you canoodle in a clear kayak in the sea.

Located outside of the Atlantic hurricane belt, Aruba is so laid-back you might be tempted just to string up a hammock near a beach and just chill. But activities like snorkeling catamaran cruises, opportunities to pilot ATVs to secret cliff-jumping beaches, or sailing trips with Champagne breakfasts are calling.

Scuba divers know Bonaire as the shore-diving capital of the world, meaning you don’t even need to board a boat to arrive at incredible reefs. This tiny Dutch Antilles island offers above-water delights too, where you can land-sail on the island’s windy side or tour a cadushy (cactus vodka) distillery. And sand doesn’t sleep on the neighboring island of Curacao, where you can kick it on Kenepa Beach or café hop in Willemstad’s historic downtown neighborhood, Otrabanda.

Shaped like a papillon (French for butterfly, the language primarily spoken here), Guadeloupe feels like a piece of Europe plopped down in the Caribbean—the island remains a French colony today. Come here to escape mass tourism, set off on snorkeling and sailing day trips to the intrepid offshore islands of Les Saintes, SUP through mangrove tunnels, and clink glasses of the local rum infused with locally grown mango or passionfruit.

Neighboring Martinique is also known for rum, fabulous cuisine, and some of the best snorkeling and diving in the Caribbean. Meanwhile, Dominica is a rugged paradise of black-sand beaches and mountainous trails that call to adventurers.

Home to nutmeg and cocoa factories, waterfalls galore, and the rushing Balthazar River (it’s perfect for tubing, this West Indies island off the coast of Venezuela is a true spice island and a real Caribbean surprise.

Grenada’s beaches range from the golden crescent at Grand Anse to black-sand volcanic stretches, complete with a backdrop of dense palm foliage. When you need a break from beaching it, hike around Grand Etang National Park or chase waterfalls at Seven Sisters.

It’s all about catching as many distinct views as you can of Gros Piton, the towering twin peaks that are St. Lucia’s most famous landmark. Explore the island’s thundering waterfalls and mud baths when you’re not basking on the beach. Hilly island roads wind from Castries to Soufriere on the island’s west coast, where the joy is in the journey—roll the windows down and take in the stunning views.

Barbados is on the hit list for surfers in the know. Some of the island’s most consistent waves roll in at Soup Bowl, a prime break in the laid-back town of Bathsheba Beach on the island’s east coast. When you’re not chasing surf, head out on a catamaran tour from the capital, Bridgetown, to snorkel above a shipwreck and spot sea turtles among the many tropical fish swarming the island’s reefs.

You can also head underground via tram into Harrison’s Cave or explore the island coast-to-coast to visit spots like Speightstown and North Point, where the Caribbean meets the wild waves of the Atlantic.

These gorgeous sister islands in the Lesser Antilles are a favorite among boaters and beach bums who just want to plop down on the sand with a rum drink in hand. There are approximately 365 beaches in Antigua and Barbuda, so you could hit a new one every day of the year if you can swing the vacation time.

Getting out on the water is always a good call, so consider a powerboat tour that traverses Antigua, with stops to snorkel at Rendezvous Bay or swim with the island’s famous stingrays. For those who prefer to stay on dry land, UTV tours take you through scenic villages and past beautiful beaches.

With the next island always within eyeshot (no maps required), line-of-sight sailing attracts yachties of all types to the US Virgin Islands and the British Virgin Islands for the Caribbean’s best sailing. If you haven’t chartered a boat of your own, head out on snorkel and sail catamaran tours from Frenchman’s Cove in the USVI to visit uninhabited Little Buck Island National Wildlife Refuge for some of the clearest waters and best snorkeling around.

The BVI is full of private boat charters where floaties, snorkeling gear, snacks, and all the Champagne and cocktails come included. Or just kick it with a rum drink on the famous sands of Cane Garden Bay during a Tortola Beach tour. The Cayman Islands are also worth a stop while you’re in the region. A snorkeling tour at Starfish Point and sandbar Stingray City offers a glimpse of the pristine marine life that lives in the Cayman’s waters.

Bachata beats and long sweeps of sand lined with swaying palm trees create the intoxicating backdrop of the Dominican Republic. And if you’ve come for adventure, you’re in the right spot, with jungles, caves, rivers, and islands to explore.

Hop an all-terrain vehicle for a tour of the island’s rugged interior to sample coffee and chocolate at an organic farm before descending to see an underground river. Board a speedboat for day trips to gorgeous Saona Island to snorkel in the clear blue shallows and relax with an open bar and typical Dominican lunch, or explore the mainland on horseback and zipline tours.

Kittitians know how to have a good time, as do locals on the neighboring island of Nevis. And if you come to these islands in the West Indies, it won’t be long till you’re invited to “lime”—that’s island-speak for the art of hanging out and enjoying life together, usually while listening to music and throwing back some food and drinks.

You can lime on the water when you board a boat with an open bar in Frigate Bay around St. Kitts and Nevis, with stops in private coves to enjoy. Afterwards, get your adrenaline going on ATV tours through sugar cane fields under the shadow of towering volcanoes, then find a beach at sunset to lime and wind down from all the day’s adventuring.

St. Vincent comes alive in its vibrant capital, the port city of Kingstown, which is your launching point for experiencing the island’s natural side. It’s all about being on and in the water in St. Vincent and Grenadines, a longtime favorite port of call for sailors where you can tour the island to see where scenes from Pirates of the Caribbean were filmed and get the history lowdown in spots like Fort Charlotte and Wallilabou Heritage Park. Enjoy more water fun at spots like Dark View Falls, where two cascades plunge into a natural swimming pool.

Beloved by cruisers and independent sailors as much as the all-inclusive crowd and independent travelers, St. Maarten promises a little something for everyone on its sandy shores. If you’re a water baby who wants to spend every minute splashing, this island’s got you covered.

Pick your perfect vessel for getting out on the water, like a speedboat to snorkel both the French and Dutch sides of the island, a luxury catamaran equipped with a Tarzan swing, or under sail to gorgeous Anguilla and Prickly Pear Cay that leaves from Simpson Bay.

Trinidad and Tobago are a Caribbean apart, offering two different worlds on two very different islands. Larger Trinidad is famous for its colorful Carnival celebrations held every February, while nature reigns on the smaller island of Tobago. But both islands are renowned for their rich culinary heritage, complete with Indian, African, and European flavors.

Head to Trinidad for the chance to see sea turtles in the east coast village of Matura from mid-March through the end of August. Port of Spain, the capital, has some of the liveliest nightlife in the islands, as well as a unique history. In Tobago, go scuba diving and snorkeling on gorgeous reefs and or have bioluminescent adventures.

Editor's note: Travel to Haiti isn’t recommended due to serious safety risks in this area. Please follow your government's guidance and travel advisories.

Haiti occupies the left-hand side of the island of Hispaniola, which it shares with the Dominican Republic—and it often gets overlooked for it's better-known big brother. But travelers who seek out Haiti are rewarded with intrepid adventures. Near the beautiful seaside coffee-trading city of Jacmel, along Haiti’s southern coast, the Bassin Bleu (Blue Waterfalls) is a series of refreshing waterfalls and turquoise pools with natural limestone waterslides down which you can glide. But for a real deep dive into Haiti’s highlights, embark from the capital, Port-au-Prince, to the island of La Gonave for an insider tour.