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Cracking the Caribbean: Three Islands, One Epic Journey

Cracking the Caribbean: Three Islands, One Epic Journey

Winter's almost here, but it's not too late to peace out.

Cracking the Caribbean: Three Islands, One Epic Journey

Photography by Brandon Presser.

No longer just a long-weekend escape or a brainless beach honeymoon, the Caribbean has been reimagined — a result of our collective obsession with small-batch charm. All-inclusive vacations are now being traded in for trips that offer an untapped reservoir of tropical appeal and a palpable sense of place. 

This new breath of life is largely due to the sudden increase in air routes (a by-product of the uptick in the economy), which provides an opportunity for younger airlines to broaden their demographics and scope. With additional direct flights being added each season, a new transit trend is emerging that pairs nicely with travelers’ rediscovery of the tropics: the island road trip.  

Consider the following as New Caribbean 101, an updated guide to seamless multi-stop vacationing: Fly directly down to Puerto Rico, jump over to St. Barth, continue on to Antigua, then zip back to the continental U.S. without ever having to backtrack.

Island Hopping Simplified

With a massive increase in connections and affordable tickets, the Caribbean should no longer be considered a constellation of singular getaways. Now it’s easy to hop between islands on reputable carriers like JetBlue (, which not only provides rapid and regular service to several key destinations in the region but also offers in-house “Getaway” packaging services tying flights and hotels together. Pair JetBlue’s regular connections to its Caribbean hubs with scheduled-charter links by Tradewind Aviation (, and you’ve got yourself a streamlined itinerary. 

Islands 1

Puerto Rico 

Unfairly slammed in the Zika frenzy, Puerto Rico was suddenly the scrawny kid at recess, the one chosen last for dodgeball (this, despite comparable — and oftentimes higher — rates of mosquito-borne illness in other destinations, including South Florida). But don’t think of Puerto Rico as “the little island that could.” Locals are fiercely proud of their home and heritage, an amalgamation of Spanish, Creole, and Amerindian roots as heterogeneous as their tangy, tantalizing food. Tourism here is once again on the rise as travelers are grasping the actual probability (or lack thereof) of falling ill, and taking advantage of discounted rates. 

For locals, the island is a world-in-one destination, with ample surfing in the west, glittering bioluminescent bays in the east, and a green heart — El Yunque rain forest — in the middle. The capital, San Juan, overflows with 2 million inhabitants tucked into diverse urban pockets, and Condado, the city’s version of South Beach, is the most fitting spot for first-time visitors to hang their hat. A long boulevard runs parallel to the sea, connecting a string of high-rise hotels. In the middle is the Condado Vanderbilt (, the most prominent stay, with its elegant history emblazoned on a retro-chic facade. A complimentary glass of champagne initiates guests as they walk into the gilded lobby, but you’ll quickly find yourself in the warm waters of the infinity pool down below. 

West of San Juan, where it’s hard to tell the difference between suburbs and stand-alone fishing villages, the high palms hide the ultimate enclave at Dorado Beach, a Ritz-Carlton Reserve ( Like no other resort in the Caribbean, the hotel uses only a small amount of its acreage for construction, allowing a sizable buffer between its protected beaches and the rest of the planet. The term “hideaway” is an understatement, as guests wade in their private plunge pools, emerging occasionally to Snapchat the sizzling sunsets or thumb through fashion magazines on a chaise lounge. 

But Dorado isn’t just about cloistering yourself from the outside world — quite the opposite. Guests are encouraged to engage with Puerto Rico’s touchstones, especially its local ingredients, used both in the array of on-site eateries and at the legendary wellness center Spa Botánico. The entrance to the spa winds around a massive tree with long, elaborate branches that stretch in such an imposing fashion that it looks like some kind of biblical allegory. The retreat beyond boasts hot and cold dunking tanks and private rooms where cloves, mint, and nutmeg are woven into the tailor-made treatments.   

Condado Vanderbilt’s signature restaurant, 1919 (, also plays with native ingredients by incorporating them into an assortment of internationally inspired dishes, including wild king salmon with local citrus. Lesbian-owned Pasión por el Fogón ( in Fajardo is a must too, showcasing island staples like mofongo, a plantain-based dish with savory stewed veggies and meat. 

Most of the island’s colonial charm is consolidated along the cobbled streets of Old San Juan, billed as the second-oldest settlement in the New World (after Santo Domingo in the Dominican Republic). Private mansions and apartments line the narrow roads, each one brightly painted from a swatch book of Skittles colors, enlivening the urban arteries connecting the stone-cut churches to the statue-strewn park plazas. Further on, tombs rise high from the knolls in the strangely scenic cemetery along the sea, the smell of baked bread wafts out of windows, and the piragua (shaved ice) carts clickety-clack as they negotiate the uneven pavers. 

The rooms at centrally located El Convento ( were, like the name suggests, once a part of a 1650s abbey for Carmelite nuns, built across the street from the oldest cathedral in the Americas. Today, the canary-yellow relic still retains many of its attributes from the conquistador era, including several cells now used as a compelling event space and a vast interior courtyard with patio furniture. The faint touches of modernity merely enhance guests’ comfort — most of the design remains resplendently historical, save for the refreshing plunge pool on the roof, which sports views of the city below.    

The hotel’s dedication to old-school Puerto Rico (burgundy Spanish tiles, wrought-iron balconies) translates to the service as well. Coffee and tea are always on offer in the common areas, and the nightly wine-and-cheese hour is complimentary. And, by request, the staff will gladly organize a private walking excursion down the colonial laneways. 

Islands 2

St. Barth

More than anywhere else in the Caribbean, St. Barth has essentially become a brand — unreasonably priced tote bags stitched with the island’s name practically fly off the shelves of the harbor shops in Gustavia. Synonymous with the high life, the Francophone island is often regarded as a high-end sanctuary for celebrities and the elite. But what is St. Barth really like? 

Established in the 1640s, Saint Barthélemy was initially a place of great hardship, owing to its arid climate and scarce fresh water. Settlers were devout Catholics, erecting stone chapels in the tropical heat, then performing penance in the darkness within. But its perfect beaches, perhaps the best in all the Caribbean, couldn’t be kept a secret forever. The first generation of jet-setters arrived in the 1950s and colonized the island with private beach homes. Today, the duality of provincial charm and high-roller glitz perpetuates its conflicting perceptions, like an island version of Kim Kardashian. 

Le Guanahani ( best exemplifies the St. Barth of our imagination: lavish cottages, champagne clinks, and guests in loose linen, all set along a backdrop of aquamarine. And the resort truly excels in the details, from the Clarins products in the bathrooms to the perfectly painted gingerbread trim hand-carved into the eaves of every roof. The property negotiates the island’s lack of real estate by constructing its cottages in an almost-linear fashion up from the beach along the cactus-clad hills. So while a cluster of rooms sits away from the sand, they all have views of the blue betwixt sun-bleached palms. 

Reflecting its Frenchness, the resort also places a great deal of importance on its food. Casual lunches on the beach come with freshly caught seafood, and Bartolomeo, Le Guanahani’s fine-dining option, elevates Creole seafood recipes by passing them through a gourmet lens. Secluded in a gated garden, the restaurant has earned a solid reputation throughout the island, attracting a smattering of patrons beyond the hotel, from locals celebrating birthdays to Oscar winners on holiday. 

Islands 3


There’s something about Antigua that feels workaday and less rarefied than the islands nearby, perhaps because it’s a country in its own right and not governed by a parent nation across the sea. And in a way, the sinuous whitewood trees haphazardly growing along the roadside — instead of perfectly planted Sunset Boulevard palms — make visitors feel like they’re experiencing a real place and not some kind of adult Disneyland. 

For such a large island (relative to its leeward neighbors), it’s surprising how few standout resort options exist along Antigua’s signature turquoise waters. Many consider it a destination of condo rentals catering to an older U.K. clientele escaping the British weather. 

Americans seeking something with less of a commitment should poke their beach umbrella in the sands of Blue Waters Resort & Spa (

Operating as a full-service resort for more than 50 years, Blue Waters was one of Antigua’s pioneers of high-end hospitality. Today the property continues to thrive, using a traditional Caribbean service model in which smiles and personality are paramount — the management, for example, opted to name the beachside bar after its affable bartender Veronica, a refreshing alternative to “Paradise Bar.” 

But paradise this place is, and beyond the warm welcome all guests receive, there’s an accompanying retro clubhouse vibe that permeates its gently manicured grounds. Sure, a significant portion of the resort has been given a face-lift, but there’s something wonderfully throwback about the older rooms on the sunset side of the property — especially Rock Cottage, Blue Waters’ largest private villa and pièce de résistance. 

 Built upon a thin peninsula, Rock Cottage blurs the line between indoor and outdoor living space, allowing the trade winds to breeze through. The architecture recalls Capri, highlighting the wraparound windows of the master bedroom and the cantilevered balconies with unobstructed views. The best part? Guests can jump off their private pier and swim to a hidden beach nearby.

In addition to an eclectic assortment of room configurations — from cove-facing hotel units to multi-room bungalows — and a calming spa bedazzled with bougainvilleas, Blue Waters also provides an optional all-inclusive food and beverage service. Travelers preferring a more boutique atmosphere needn’t go running for the hills, though — the menu items are less buffet and more an extension of the resort’s real-deal Caribbean vibe: local slaws and spices and delicious outdoor barbecues.

Beyond the resort, be sure to check out the classic panorama views from Shirley Heights down to the historic quarter of English Harbour and the hands-on Stingray City experience in Mercers Creek Bay. But with all of the Antiguan hallmarks already packed into Blue Waters, you wouldn’t feel guilty for never leaving its premises.  

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Brandon Presser