Find the right Caribbean island, from luxurious St. Barths to budget-friendly Puerto Rico
The Caribbean is so much more than surreal turquoise water and idyllic beaches that keep people around the world coming back for more. There are thriving cultures rooted in complex histories of conquest and victory, an evolving culinary scene deeply tied to indigenous flavors and modern twists, historical landmarks with stories behind its walls, and natural wonders that sit on hillsides and ocean floors.
To explore this region, you’ll need to decide what you’re looking for: adventure, an incredible meal, something that won’t break the bank, or just a nice, strong glass of rum and ocean view.
Here are some picks that will get you closer to your ideal Caribbean getaway based on what you want out of your trip:
Beaches: Anguilla
You’d be hard-pressed to find a Caribbean island that doesn’t have at least one stunning beach, but Anguilla manages to inch out ahead of the rest for a few reasons: jet skis and large cruise ships are not allowed on the island, meaning, unobstructed views as far as the eye can see. And the only thing clearer than the ocean views here is the water. Anguilla’s 33 beaches are so stunning, they even give the famous stretches of sand in the Maldives a run for their money.
Where to stay: Located on one of the island’s most beautiful beaches, Meads Bay, Four Seasons Resort and Residences Anguilla is the perfect home base for any ocean lover. its 35 acres of prime beachfront property are encircled by powder white sand and a turquoise ocean, with Caribbean-inspired accommodations. The stunning five-bedroom beachfront villas – available to rent or purchase – give families more than enough room to play with a pool, outdoor shower and oceanfront terrace to take in that famous turquoise Anguilla water.
What to do: You can’t go wrong with any of the beaches in Anguilla, but for calmer waters and views of the neighboring island of St. Martin, head to Rendezvous Bay on the southwest coast. Shoal’s Bay on the northeast coast will satisfy with less crowds and a shimmering blue ocean. Or, have your own adventure on Prickly Pear Cave’s luminescent waters.
Nature: Dominica
Nature puts on the most elaborate, five-star show in Dominica. Steep, green mountain peaks, rivers, waterfalls and the world’s second-largest hot spring (Boiling Lake) are just a few reasons Dominica – situated between Guadeloupe and Martinique – is called “The Nature Island of the Caribbean.”
Where to stay: Secret Bay feels like just like its name: a place too good to share with the rest of the world. The boutique hotel has just six sustainable villas nestled on a beautiful cliffside on the northwest coast. You can start the day with yoga in the property’s open-air pavilion and end it with a Caribbean cooking class.
What to do: Whether you’re a hardcore adventurer or want to go at a slower pace, it won’t be hard to get active on this natural wonderland. Explore beaches by kayak, hike the mountainous landscape, swim in the island’s Emerald Pool, or rappel down waterfalls. Don’t forget to enjoy the island’s rich Creole heritage as well, with foods like crabback (spiced local crab) and callaloo (leaf stew) and folkloric, African inspired dance, called bélé.
Luxury: St. Barths
Get a slice of the French Riviera right in the heart of the Caribbean. Think sunbathing bodies draped in designer clothing, the sound of champagne bottles being popped open, and a culinary scene that the French are famous for. But don’t let the glitz discourage you: St. Barths’ locals are incredibly friendly and laid back. To avoid getting seasick on the ferry ride, Tradewind Aviation offers nonstop flights to St. Barths from San Juan, Puerto Rico. The landing onto the island is thrilling – as it is one of the shortest in the world.
Where to stay: Le Barthelemy Hotel Spa has a prime location in the serene Grand Cul de Sac, and is ideal for travelers craving an intimate luxury hotel without pretension. The laidback hideaway offers 44 rooms and suites, each with a terrace and many with private pools. To unwind, there’s a cozy spa with plunge pools and La Mer products. At the rooftop bar, Whiskey Tango Foxtrot, guests can enjoy tapas and crafted cocktails made in glasses shaped like blowfishes.
What to do: Enjoy a day aboard one of MasterSki Pilou’s yachts, where you can get a tour of the island’s coastline with stops to snorkel and sunbathe. Afterward, dine with the cool kids at the iconic Nikki Beach for an oceanside lunch. When you’re ready for a workout, with a reward hike to one of the island’s natural pools. For dinner, Bonito is the island’s hotspot with marina views and ceviches that are sinfully good.
Party: Trinidad
There are a number of terms used in Trinidad that all center around one thing: having a good time. A party is a “fete,” meeting up with friends is “limin’ ” and dancing until your feet hurt? Well that just means you’re “winin’ ” or “gettin’ on bad.” If you love to get social until the early hours of the morning, this is your island, particularly in February for the greatest celebration on earth: Carnival.
Where to stay: The centrally located Hyatt Regency is a favorite for Carnival goers, tourists and business people. The waterfront hotel has 422 rooms and rooftop pool, best enjoyed with a rum punch in hand.
What to do: Ariapita Avenue has a number of bars, street food and restaurants to fuel your night. When hunger calls, don’t miss Trinidad’s most beloved finger food: doubles. This messy delight includes curried chickpeas stuffed between two pieces of fried bread (called barra). It can be topped with condiments that are sweet and spicy, like tamarind and pepper sauce. During Carnival, groups (called bands) dance to soca music on Carnival Tuesday (their Mardi Gras). There are endless fetes to enjoy, on boats, beaches and hillside villas. Pace yourself: during Carnival, there’s no such thing as “tired.”
Romance: Saint Lucia
Driving from Saint Lucia’s north coast to its south, it’s impossible not to be wowed by the sprawling jungles, hillsides and valley views of the ocean below. There’s a stillness to it all, uninterrupted by traffic, blaring horns or high-rise hotels. St. Lucia’s lush environment and tranquility make it ideal for couples looking to unwind.
Where to stay: Honeymooners and couples cuddle up at Sugar Beach, a Viceroy resort, because of its idyllic location in the southern town of Soufrière. From the property’s two white-sand beaches and many of the hillside villas, you can spot St. Lucia’s iconic Piton Mountains. Ninety-six suites, including 28 standalone villas, cottages and residences sit on over 100 acres of lush jungle. The Friday night BBQ is a feast that includes a buffet and live music.
What to do: Chocolate anyone? There are a number of romantic activities to enjoy in St. Lucia, including enjoying this sweet aphrodisiac. Saint Lucia’s volcanic soil helps to produce some of the world’s best chocolate, and you can enjoy everything from chocolate farm tours, chocolate and wine pairings at the renowned Jade Mountain Resort, and cocoa infused body scrubs.
Budget: Puerto Rico
Puerto Rico is a destination filled with vibrant culture and beauty that can be discovered for free or very low cost. Whether you’re roaming the streets of Old San Juan or getting close to nature at a beach or river, it’s easy to navigate the island without breaking the bank.
Where to stay: Located on the popular Isla Verde beach, Intercontinental San Juan has recently reopened its doors. The 398-room property underwent an impressive, multi-million dollar renovation that includes four restaurants and lagoon-style pool with swim-up bar.
What to do: Take in the 500-year-old architecture of Old San Juan, as well as some shopping for incredible Puerto Rican coffee (Café Oro is a favorite) and a piña colada from Barrachina. In the El Yunque rainforest, you can hike and experience the coqui tree frogs and majestic waterfalls. Public beaches are plentiful, with Isla Verde and Condado being the most popular in San Juan, and the more remote Culebra and Vieques just a ferry ride away. Lote 23 is an open-air food truck court that is perfect for a nice day out. Come hungry. On Monday nights, La Terraza de Bonanza is the place to be for live bomba music and cheap eats that include tostones and empanadillas.
Culture: Havana
In Havana, you’re not going to get a luxury vacation where you’ll barely need to lift a finger – and that’s a good thing. It goes without saying that this Caribbean island’s complicated relationship with the U.S. has kept many of its advancements at a standstill – but one thing that always thrives is Cuban culture.
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Where to stay: American tourists are restricted from staying in government-owned hotels, but luckily, AirBnBs are plentiful and a much better opportunity to learn more about Cuban culture with a host family. For a central location in Old Havana, Casa Obispo 307 is a comfortable option with balcony views of bustling Calle Obispo.
What to do: AfroLatino Tours offers an intimate look into Havana’s rich and complicated African culture and spirituality. You’ll spend the day touring a Yoruba museum, followed by a private dance and drumming performance. For city tours via car and foot, Tour Havana with Roly is informative and flexible with tight schedules. For live music and drinks, Sia Kara does not disappoint (especially with its mango mojito). On Wednesday nights, the Interactivo showat Bertolt Brecht is one of the best live performances you’ll catch on the island.
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Off the Grid: Ambergris Cay
If “do not disturb” is one of your favorite mottos, Ambergris Cay is definitely the island for you. This private island in the southeastern chain of Turks and Caicos is about a 20-minute plane ride from Providenciales and once you arrive, you’ll truly feel like you have the whole island to yourself.
Where to stay: Ambergris Cay is both the name of the resort and island. On this three-mile-long paradise, it’s easy to strike a balance between exploration and doing absolutely nothing at all. Caribbean-inspired decor in 10 beachfront suites and three villas are brought to life by Dutch designer Nicole van Schouwenburg.
What to do: For an island so small, there is surprisingly a lot to do – should you choose to. Each all-inclusive experience comes with a golf cart to navigate the island, 24-hour room service, a daily, 30-minute spa treatment, kite-surfing lessons and guided nature walks.
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