9 top experiences for your next Caribbean getaway

Pitons Bay anchorage Saint Liucia
A sailing excursion in and around lush St Lucia is one of the most romantic ways to pass a day in the Caribbean © LOW FLITE / Getty Images / iStockphoto

To the uninitiated, the Caribbean appears to be a cluster of islands sprinkled across azure waters. But all islands are not created equal.

This archipelago contains 13 independent countries and even more semi-autonomous territories, occupying some 700 islands spread over over a million square miles. Known worldwide for its music, food and spirits, the region is a true cultural crossroads, too, where English, Spanish, French, Dutch, Creole and other languages are all spoken. The one common thread tying these multicultural islands together? Unforgettable experiences. From floating bars to cross-country trails, here are some of the best things to do in the Caribbean. 

Immerse yourself in the best experiences the world has to offer with our email newsletter delivered weekly into your inbox.

Head out to Captain Oak’s Tiki Bar in Turks and Caicos

A bar might seem a humdrum choice in a place as stunning as the coral islands of Turks and Caicos. But hovering in the center of Long Bay Beach is Captain Oak’s Tiki Bar, a watering hole that floats – literally. Take a jet ski over or hop on one of the bar’s ferries to cross the impossibly turquoise waters for some local beer and light fare. 

Woman scuba diving on the reef off the Dutch Caribbean island of Saba
The unique ecosystem of tiny Saba make its waters among the best in the Caribbean for scuba diving © timsimages.uk / Shutterstock

Go diving in Saba

Saba is a 5-sq-mile island between St Maarten and St Kitts so tiny it’s often left off the map. But a trip here is well worth the journey, as Saba’s volcanic origins have created an ecosystem that’s a diver’s dream. Take the plunge at one of several prime dive sites on the small island, including Tent Reef (great for nocturnal spottings during night dives), Diamond Rock and Eye of the Needle. 

Visit Store Bay beach in Tobago 

Trinidad’s lesser-known sibling embodies the chill vibe the Caribbean is world-famous for. And since its visited by relatively few tourists, the beaches here are extremely laid-back. We recommend Store Bay beach on the island's southwestern coast, just minutes away from Robinson International Airport. Here, the powder-fine sand borders calm and shallow emerald-blue water with nary a wave in sight. There’s even a small reef for snorkeling on the beach’s western edge.

Stop by one of the stalls – Miss Trim’s or Miss Jean’s will do – for a portion of yummy crab and dumpling (Tobago’s national dish) or bake and shark (the fried-fish flatbread that’s a Trinbagonian favorite). The proximity to the airport makes it the ideal spot to catch the final orange glow of the gorgeous Tobago sunset before your departure.  

Visit the Bob Marley Museum in Jamaica

In a land that has produced a slew of international music and sports stars, reggae icon Bob Marley is surely the most famous Jamaican who ever lived. His music is so timeless, his global impact so profound, that visitors can’t get enough of the Kingston museum that celebrates his legacy.

His former home on Hope Road has been fashioned into an immersive exhibition of Marley memorabilia, including gold and platinum records, costumes, his Grammy Lifetime Achievement Award, a 3D hologram from his 1978 One Love Peace Concert and rare photographs. Every room, including the recording studio, has been preserved exactly as it was when Marley lived there, bringing fans up close to the master and his world. 

A wooden sign on segment 5 of the Waitukubuli National Trail long-distance hiking path in Dominica
Dominica’s rugged, long-distance Waitukubuli National Trail provides a Caribbean experience for outdoors enthusiasts © Tom Madge-Wyld / iStock Editorial / Getty Images Plus

Hike the Waitukubuli National Trail in Dominica

Most Caribbean islands beckon visitors with white-sand beaches and deep-blue waters. On the other hand, rugged Dominica offers a topography of deep gorges, seemingly untouched forest and mountainous terrain all ideal for adventurous spirits. Hiking is an understandably popular pastime here, and the Waitukubuli National Trail – at 114 miles, the longest in the Caribbean – offers visitors a vigorous way to traverse the island.

Taking visitors from Scotts Head at the southern tip of the island to Cabrits National Park at the northern end, with 14 segments in between, the entire trek can be completed in two weeks. The hike offers a highlight reel of the Nature Isle’s treasures, including Boiling Lake, Morne Trois Pitons National Park World Heritage Site and Morne Diablotins; innumerable rivers and gushing waterfalls; and encounters with the indigenous Kalinago people. The trail is well marked, with ample rest stops and shelters along the way. 

See the underwater sculptures in Grenada

The world’s first underwater sculpture park is just off Grenada’s west coast. At this unique attraction, the sculptures have become so seamlessly integrated into the seabed that it’s easy to imagine they’ve been there for hundreds of years. But that’s not the case.

The park opened only in 2006 and has grown to include 75 sculptures crafted from concrete and steel, each weighing up to 15 tons. And the works serve more than just aesthetic ends, too: they are all intended to aid in conserving and maintaining a healthy subaquatic ecosystem. Standout sculptures including Christ of the Deep, The Vicissitudes and The Lost Correspondent can be accessed via a glass-bottom boat or snorkeling excursion – though a scuba dive is really the best way to get extended time in this one-of-a-kind art gallery. 

Go sailing in St Lucia

St Lucia is an island for lovers – particularly water lovers. Flanked by the Caribbean Sea on the west and the Atlantic Ocean to the east, the island offers mountainous beauty that can easily admired during a boat trip. Book a catamaran day trip along the scenic western coastline to Soufrière, where the majestic Pitons await. The magical Toraille Waterfall, therapeutic Sulphur Springs and idyllic Anse Cochon Beach – a perfect spot for some snorkeling and swimming – are just a handful of possible stops during a daylong excursion. Another option is a stirring late-afternoon cruise, during which you can sip champagne and enjoy an unfettered view of the sun slowly dipping below the horizon. 

A local kid plays in the sand in front of buses at Deep Bay Beach in Antigua
Decompressing on Deep Bay Beach in Antigua is never a bad idea © Leonard Zhukovsky / Shutterstock

Go to the beach in Antigua

It’s almost impossible to go to the Caribbean without hitting up a beach – and beaches are all but inescapable in the twin-island nation of Antigua and Barbuda. Antigua in particular is known for having a beach available for every single day of the year – there are a cool 365 of them along its shores. A clear standout is crescent-shaped Deep Bay Beach, at which you’ll find serene, gin-clear waters more reminiscent of a large pool than a major body of seawater. Take a leisurely swim or snorkel to the bay’s center to explore the 100-year-old sunken shipwreck. And don’t leave without climbing to the ruins of nearby Fort Barrington, overlooking the beach, to absorb the beautiful panorama below.

Take a Barbados rum tour

Barbados is touted as the birthplace of rum, thanks to its history of sugarcane production (using enslaved labor) and a tropical climate ideal for the maturation of spirits. Distilleries like the venerable Mount Gay (said to be the oldest in the world), the architecturally stunning St Nicholas Abbey and the intimate Foursquare Rum Factory provide deep dives into the rich history of rum making as well as samples of their products. The Rum Vault at the Colony Club Hotel houses a collection of over 150 regional and international rums, serving them up with dinner and tapas pairings. And for an unbeatable local experience, shoot the breeze with Bajans on a tour of the many rum shops sprinkled across the island

Buy Armchair Explorer

Lonely Planet's Armchair Explorer

Journey through the best films, books & songs from 120 countries. Perfect preparation for travelers or simply a satisfying journey into the unknown, this book lists the 5 most interesting books and movies from each country, plus its top 10 tunes.

Buy Armchair Explorer

Explore more places