The Caribbean is a mosaic of diverse destinations, each with its own history, culture, and breathtaking scenery.
A treasure chest of over 700 islands, islets, reefs, and cays scattered liberally across the Greater and Lesser Antilles, this wealth of options can sometimes overwhelm travelers, spoilt for choice in this natural paradise.
Whether you’re a history buff, a sun worshipper, an eco-adventurer or simply looking to disconnect from the world, our pick of the best Caribbean destinations each promises a distinct and unforgettable journey.
1. Soufrière, St. Lucia
Best for natural attractions
This colorful waterfront town along the southwestern coast was originally the island’s capital before that designation went to Castries. However, it still gets top billing on any St. Lucian travel itinerary.
The primary attraction in the area is the Pitons, two soaring volcanic peaks that emerge dramatically from the seabed. The larger of the two, Gros Piton, is also the more manageable hike (Petit Piton is generally off-limits).
A delightful detour to Au Poyé Park at the base of the Piton, and just five minutes from the trailhead, rewards you with luscious ice cream crafted from local fruits.
If climbing is not your cup of tea, there are plenty of other scenic spots, such as the more accessible Tet Paul Nature Trail – bask in unfettered views of these iconic volcanic plugs set against the cerulean blue seas. When you’re finished exploring, rest your aching muscles in the rejuvenating Sulphur Springs, the remnants of a collapsed volcanic crater.
These mineral-rich waters, infused with magnesium and calcium, are believed to have healing properties and offer a unique and invigorating spa-like experience.
Afterward, cool off at one of several waterfalls that dot the landscape, including the Toraille Waterfall, Piton Falls, and Diamond Falls.
Planning tip: Climbing Gros Piton can take anywhere from three to six hours. Set off early when temperatures are cooler, and dress comfortably (no flip-flops!). Pack sufficient water and sunscreen.
2. Old San Juan, Puerto Rico
Best for history
The charm of Old San Juan lies in its blend of centuries-old architecture with the lively spirit of its people. The city center is a maze of buildings washed in bold hues, from maize yellow to cornflower blue, each adorned with intricate wrought iron balconies and heavy wooden doors.
Check yourself into the newly renovated Hotel Rumbao – it’s strategically positioned within walking distance of practically every landmark and offers a respite from the city bustle.
A short walk will take you to the sprawling 27-acre Castillo San Cristóbal, the largest Spanish fort in the Americas, or to the Calle Fortaleza, a slate cobblestone road adorned with decorative canopies and one of the oldest and most photogenic streets in the area. A leisurely stroll along Paseo de la Princesa just before sunset reaps romantic views of the bay and the majestic Castillo San Felipe del Morro.
When it’s time to dine, the in-house Island Kueros Bar & Kitchen beckons with a tantalizing spread, including the Signature Coquito French Toast, Torched Tuna Poke Pegaitos, and Coffee Rub Ribeye Steak.
Pop into Raíces along Calle Recinto Sur for their flavor-filled mofongo with churrasco and refreshing local fruit juices. Go early to beat the long lines and get your name on the list.
3. Les Anses d’Arlet, Martinique
Best for beaches
Les Anses d’Arlet, hidden away on the southern coast of Martinique, is a picture-perfect fishing community where time seems to flow as slowly as the gentle waves that lap its shores. Several beaches, each with their own distinct character, grace the coastal village.
Powdery blond sand frames the tranquil and gin-clear turquoise waters of Plage du Bourg. It’s the perfect accompaniment to the glorious Église Saint-Henri backdrop; hundreds of tropical fish swarm around a rock formation called “la kay” on the nine-foot-deep sea bed, making this an excellent spot for snorkeling.
A bit further north, Grande Anse’s white sand and placid waters make it a popular tourist spot. It’s the largest beach in Les Anses d’Arlet, with unimpeded views of Rocher du Diamant (Diamond Rock). Sip on a Ti Punch (the national cocktail) at one of the nearby small restaurants.
Neighboring coves Anse Noire and Anse Dufour present a peculiar contrast. The former’s signature black sand is the result of the region’s volcanic past, while Anse Dufour’s pale sand is a byproduct of eroded shells and corals just a few hundred meters away.
4. The Indian River, Dominica
Best for unwinding
The Indian River, flowing into the Caribbean Sea, stands out as the most celebrated of Dominica’s 365 rivers. The journey begins at the visitor’s center just outside Portsmouth, near the bridge, where you can arrange a guided boat tour.
The dense overhead thicket offering mere slivers of daylight and the tangled roots of Bwa Mang trees snaking along the riverbank evoke a cinematic feel.
The dramatic atmosphere may have influenced the area’s selection as a “Pirates of the Caribbean” filming site. Typical stops on the tour include a visit to Cobra’s Bush Bar, home to the famously potent “The Dynamite” cocktail.
Stop at Madiba Beach Café, an outdoor haunt right on the sand. It serves fresh seafood, and the rustling waves provide a soothing soundtrack. Be forewarned: their homemade rum and raisin ice cream is positively addictive.
5. Northern Grenada
Best for foodies
Grenada, also known as the Spice Island, is a delightful exploration of flavors and is the perfect choice for foodies. Dive deeper into Grenada’s spice legacy with a visit to the Nutmeg Museum, showcasing the island’s pivotal role in the global spice trade.
Those with a sweet tooth will revel in a tour of the Jouvay Chocolate Factory, featuring some of the world’s finest organic chocolate.
For lunch, head to Belmont Estate, a true farm-to-table experience amidst lush, verdant surroundings – the nutmeg ice cream is a revelation. Cap off your visit with a trip to River Antoine Rum Factory, the oldest running water-propelled distillery in the Caribbean, where you can sample potent (up to 150-proof!) local rum, which reportedly wards off hangovers.
6. Oistins, Barbados
Best for seafood lovers
This lively fishing village transforms into a vibrant culinary hotspot every Friday and Saturday night, hosting the famous Oistins Fish Fry, where locals and tourists converge to feast on freshly grilled marlin, tuna, swordfish, lobster, mahi-mahi, and the legendary flying fish – a Bajan specialty.
Typical sides include rice, breadfruit, macaroni pie, and, of course, the local delicacy cou-cou (a thick paste of cornmeal and okra).
You can savor your meal on the water’s edge and throw back a frosty Banks beer, accompanied by the rhythms of calypso and reggae, or see if you can triumph in a sure-to-be raucous game of dominoes.
7. Montego Bay, Jamaica
Best for partying
“MoBay” is famous for its lively nightlife and hosts some of the island’s most energetic beach parties and music festivals. The Hip Strip, officially known as Jimmy Cliff Boulevard, is lined with clubs, bars, and beaches where the party goes from sunset to dawn.
Places like Pier 1, renowned for its Friday night parties with live music and DJs, and Margaritaville, which transforms into a buzzing nightclub after dark, are staples for night owls.
Party nights at Lounge2727 are like no other, with hookah, a dispensary, cocktails, a dance floor, and DJs playing hip-hop and dancehall music until daybreak.
It makes sense that Jamaica would host the hottest parties given it’s the birthplace of musical legends like Bob Marley, Beenie Man, and Sean Paul, whose rhythms have shaped the island’s soundtrack and influenced global music trends.
8. Canouan, Grenadines
Best for disconnecting
The undeniable appeal of Canouan is reflected in its unspoiled beaches and the private villas peppered throughout the scenic landscapes. The most tranquil yet lavish experience awaits at the Mandarin Oriental Canouan, which hugs Godahl Beach. This exclusive resort is an oasis away from the constant buzz of typical tourist spots.
With beaches where the only footprints are likely to be your own and more turtles than traffic, Canouan is a sanctuary for peace and privacy.
If you want complete seclusion, it’s worth the 20-minute sail to Tobago Cays. This group of five unpopulated islands is home to a protected coral reef that offers world-class snorkeling.
This article was first published May 14, 2019 and updated Jun 28, 2024.