The Dominican Republic had a recent bright idea, offering a recovery plan that includes medical insurance to visitors in a bid to restart its tourism-dependent economy. Promoting “a responsible recovery that prioritizes health,” the tourism board is offering a temporary free travel assistance plan in effect until December 2020 to everyone visiting a hotel, that includes emergency coverage, COVID tests and cost coverage for a long-term stay. As well, proof of a negative test is no longer required upon entry into the country. Instead, random “quick tests” will be performed.

WHERE TO STAY: IN THE D.R.

This new Dominican travel insurance is a big deal and not without a hefty price tag: $28 million in promotion and financing, and $7 million in wooing plans to solidify air routes to and from. Let’s see how long it takes other Caribbean governments to haul a big bale of money down from the attic and follow suit.

GODOMINICANREPUBLIC.COM

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Mixing more than a dash of island whimsy with a the slightly button-down vibe due in part to the island’s British roots, Barbados gives you lots of opportunity—and encouragement—to let your hair down.

Hit the beach. The west and south coasts of Barbados offer one beach after another of finely ground coral sand—take your pick. Then take a Cool Runnings Catamaran cruise, go kayaking or paddle-boarding, or just sit on a lounger and enjoy the million different shades of blue. There are also dozens of dive sites to sink your mask into, with Barbados Blue at Needham’s Point Pebbles Beach being the dive shop of choice—an excellent launching point for shipwrecks in Carlisle Bay.

Eat local. The street food trucks and rum-shop takeout counters are crowded with locals and tourists for good reason: They harbour some of the most delicious home cooking you will ever taste. The Oistins fish fry is a Friday-night highlight, with dozens of market stalls sizzling with goodness. And the lineups at Cuz’s Fish Stand in the Garrison in Bridgetown are so healthy on weekdays, he takes the weekend off. For fine dining, there’s a ton of home-grown talent, notably at Hugo’s in Speightstown, where Chef Avion Caine leans on his childhood food memories to present a tantalizing, local-flavour-infused menu. For a sexy, barefoot-chic culinary experience, head to La Cabane at Batts Rock Beach for the sunset—but stay for the coconut mojitos and fresh grilled fish.

F&B: HOW TO MAKE COU-COU

Get inside intel. Spend some quality time with Chef Michael Harrison from Island Market & Food Vibes Tour, who will take you around town to the markets, then out into the countryside to taste-test the best local cuisine at places like the iconic Village Bar and the bucolic Country View Bar & Grill.

Try the rum. Barbados is by all accounts the birthplace of rum. Mega-distiller Mount Gay dates back to 1703, when it was discovered that the molasses they had been discarding after processing the sugar cane fermented quite nicely. Traditional rum “shops,” roadside bars where people gather to watch cricket and play dominos, are scattered throughout Barbados. But you need to venture outside the fray to experience the best of the island’s rum: Make sure Foursquare Rum Distillery and St. Nicholas Abbey Distillery are both on your list. Make sure there is room in your suitcase to take a bottle home.

Catch a wave. The easy-going east side of Barbados is where locals go to relax on the weekend—or surf. A day trip to the rugged Atlantic coastline of Bathsheba will reveal stunning views and a few heritage hints, particularly if you venture into the Atlantis Hotel, which dates back to the 1880s. Make a pit stop on the patio before taking a hike along the old railway tracks to watch the surfers at the Soup Bowl, a world-famous reef break. The east side is also home to the top vegetarian restaurant in town, tucked under the palm trees at ECO Lifestyle Lodge.

ALSO ON THE EAST SIDE: THE CRANE

Cheer on the ponies. When the beach gets boring, head to the sports pitch. Cricket isn’t the only game in town, either. The popularity of polo in Barbados reaches back to colonial times, the first match being played in 1884. The Polo Club regulates four playing fields, welcoming international teams in a season that runs from January through May. Prince Charles and Prince Harry have both played polo here many times.

VISITBARBADOS.ORG

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Settling into Anguilla, our little private pool overlooking Crocus Bay was just the right refreshing temperature and ditto the meltiness of the gin and tonics. And there would be time for another while we waited for the private chef we had hired for the night to work his magic in our glassed-in kitchen.

This British island just north of St. Martin/St. Maarten has one of the highest rates of repeat visitors in the Caribbean. And for good reason: The beaches are insane, the food is phenomenal, and the people are charming—a sun-spot’s triple threat. Anguilla has the right amount of semi-poshness to make it luxe, mixed with just enough normal to make it affordable.

Set up at CéBlue Villas. This gorgeous hillside resort sports five-bedroom homes, each with its own little pool, media room, kitted-out kitchen and gorgeous ocean view. It’s far enough away from it all to enjoy the serenity, but just a few minute’s drive from the heart of the island action. The Crocus Bay beach is just down the hill, complete with attendants, ample watercraft for those inclined, and Da’Vida, a cool beachfront restaurant.

Pop into the posh. The Kelly Wearstler-designed Four Seasons Anguilla is beyond dazzling. Sunset at the Sunset Lounge couldn’t be more special. People flock to this elegant waterfront bar overlooking the infinity pool at cocktail time to see how the other half lives and to prime the night with the signature Jalapeño Margarita.

Set sail. I highly recommend an afternoon of sailing from bay to bay aboard the classic sailboat Tradition, a handmade wooden boat from 1978. Book a trip to Prickly Pear Cay or Little Bay and enjoy a lobster lunch or hop on for the sunset cruise. Mind the fizzy doesn’t go to your head.

Get Scilly. Earmark Wednesday or Sunday for lunch on Scilly Cay, a tiny coral islet off the village of Island Harbour, reachable by a free, 10-minute boat ride. The whole island is a rustic open-air restaurant run by the Wallace family, who whip up Anguilla’s deadliest rum punch, plus platters of barbecued lobster, snapper and chicken. Have a punch, have lunch, then wallow in the shallow waters on the soft sandbars.

Go dancing. Live music is a huge part of Anguillan culture. Locals and tourists lap up reggae, jazz and R&B bands almost every night at the many venues scattered around the island, including the Powerhouse, Johnno’s Beach Stop, Gwen’s Reggae Grill, and the Dune Preserve, owned by music icon Bankie Banx. Time your visit to coincide with the annual Moonsplash Music Festival in March/April.

When You Go. Off-season between May and August is the best time to visit Anguilla to get prime deals and avoid the rains. Book a sea shuttle in advance to get you from the airport to Anguilla via the 25-minute ferry, which runs all day. Keep an eye out for Denzel Washington and Robert DeNiro. No, not together. Go to ivisitanguilla.com for more.

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Vibe: Visitors to the Petite Anse are after peace and quiet. Guests really fit in with the locals, who drop in for a chat, a drink or a meal. This is a good honeymoon spot, and a great place to escape to after you’ve spent some touristy time around the southern peninsula and in the fancier resorts of St. George’s.

Rooms: Eleven stand-alone, air-conditioned bungalows feature decks or terraces and hammocks to fall asleep in. Wooden flooring and simple colonial-style wooden furniture is unfussy and functional. Canopied beds have netting to swirl around you, though a steady ocean breeze here keeps the bugs away. Spacious ensuite bathrooms are more open to the elements and to the front deck. Two rooms in the main part of the hotel are also well-equipped and comfortable.

THINGS TO DO: IN GRENADA
TASTE TO TRY: GRENADA GASTRONOMY

F&B: The European-inspired dining room is a destination restaurant, with many locals stopping in, elevating the insider experience. Fruit and vegetables come from the owners’ gardens or are carefully sourced from regional farmers. Fish is sourced from local anglers. The menus change daily and also include steaks, chops, chicken and fresh salads—and homemade ice cream. A traditional breakfast of fried bread and salted fish will stick to your ribs. A lounge area is equipped with a library and stacks of board games to while away rainy afternoons.

Extras: Annie is famous for her love of animals, which roam the complex and become fast friends. She sometimes rides down from her nearby plantation house atop Darius the donkey. I played with a mischievous teenaged cat for a half-hour in my room each night at turndown until he got bored and wandered off.

Off-Site: This little retreat is miles away from the neighbours and that’s exactly how you want it. The hotel looks out to Ronde Island and Carriacou, and their surrounding little Lower Grenadine islands. The resort is a six-minute walk from the beaches of Sauteurs Bay. In the car, you’re six kilometres from Levera National Park, 11 kilometres from Belmont Estate with its plantation tours and museum, and 45 kilometres from Maurice Bishop International Airport.

Rate: $$

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Vibe: At The Crane, you will meet well-heeled American, Canadian, British and European couples, groups of friends, retirees and families who have been coming back year after year for years, including the timeshare guests who make you feel at home by being at home themselves.

THINGS TO DO: IN BARBADOS

Rooms: Mahogany absolutely everywhere. Even the one-bedroom suite feels like a small condo, your two kids bunking down in the large living room. A dining room and full kitchen (fridge with ice dispenser, dishwasher, washer-dryer) is perfect for families who want to have at least a few meals in. Bedrooms have a four-poster king-size bed and a writing desk, leading into a big bathroom with two wardrobes, whirlpool bath, separate toilet, separate shower and double vanity.

F&B: The Zagat-rated Zen restaurant is the island’s go-to for Japanese and Thai food, its private booths elegant and inviting. D’Onofrio’s Trattoria bills itself as casual family dining, but I must have dined when the children had all gone to bed. It serves the best Italian food I have ever had in the Caribbean, full stop. Sun-worshipers flip-flop into the palm grove behind the beach for hearty lunch plates at The Grove Bar & Grill.

TASTE TO TRY: TRADITIONAL COU-COU

Extras: Swimming pools for days! Even the swimming pools have swimming pools. Many ground-floor suites have private pools up to 28 feet long. Corner rooms have plunge pools in the turrets on every floor and penthouse suites have 12-foot pools with rooftop garden decks. The Crane is also equipped with a full-service Serenity Spa, a fitness centre and a kids club. (Yes, there’s a swimming pool for adults only, too.)

Off-Site: The serene beaches of the east coast are a 30-minute drive north. The south coast beaches are a 20-minute drive and you can reach the beaches and nightlife of the west coast in 40 minutes. The airport is just 15 minutes away.

Rate: $$$
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Curaçao and its capital city Willemstad form a complete vacation checklist: brilliant-blue waters, 35 white-sand beaches, a heritage comprising more than 55 different cultures (including Dutch, Spanish and Portuguese), beautiful European Colonial architecture with more than 700 listed buildings and a healthy perspective on the LGBTQ, including their own.

The benefits don’t stop there. This island of 160,000 is also outside the hurricane belt and blessed with trade winds that make it not seem quite so hot. Visitors find excellent and eclectic museums, some of the best scuba diving in the world and an actual café society due in part to the thousands of Dutch tourists who flock here year-round, including a large number of students.

• Mix up your accommodations and their locations. Spend a few days in the Pietermaai district at one of the boutique hotels, a day or two at Floris Suite Hotel (particularly for Friday night’s lobby party at 6 p.m.), maybe rent an Airbnb in the Jan Thiel area. There are all-inclusives, but you don’t really want that.

• Don’t be afraid to go out at night. Pietermaai is where the action is. Hit Mundo Bizarro for cocktails, Ginger for Asian Caribbean or Kome for a steak, then Miles Jazz Café for live music. Don’t shy away from the local food stalls and markets.

TRY THE TASTE: IGUANA STEW

• Spend at least one full day or two in Westpunt. Hike up to the top of Mount Christoffel (at dawn, before the heat begins), drop by Shete Boka National Park to see how the crashing waves have sculpted the coastal limestone, and try the iguana stew at Jaanchie’s for lunch (mind the bones).

• Beach-hopping is an actual thing. Each little bay has its own personality. Playa PortoMari has resident red pigs Woody and Willy (not kidding) to romp with, while Playa Piscado is busy with half a dozen wild turtles who clamber for treats from the local fishermen and delight the families swimming along just a few feet away. Lagun Beach is tiny and more peaceful, popular with divers and locals. Really, the whole island is a diver’s paradise with more than 60 sites.

• Rent a car right at the airport. Take note that gas is expensive.

CURACAO.COM
CURACAOPRIDE.COM

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Vibe: You know that bubbling-under house music soundtrack that sounds like nothing and never ends? That. The CHIC Punta Cana is rather a scene, but you don’t have to participate if you don’t want to. A big casino with Blackjack, Roulette and slot machines is open from noon until 3 a.m. This is balanced out with a Detox Oxygen Bar that serves recreational oxygen shots and healthy drinks.

Rooms: The 320 rooms at the CHIC Punta Cana are super modern, mostly all white with black trim and purple light. That sounds like the ’90s, but it’s actually fun; you feel like you’re starring in a Disaronno TV commercial.

F&B: The à la carte restaurants are an interesting mix: Italian, Japanese, Middle Eastern and steak house, all lavishly decorated and trying really hard. There’s a giant round bar between the lobby and the casino and a sports bar cum nightclub combo that also has billiards. This is good if you want to escape the heat for a couple of hours and watch the game, whatever your game is.

Extras: The Diamond Club upgrade is worth the splurge, as they lay it on thick: butler service, better room-service menus, private check-in lounge, exclusive pool and beach areas, and a Club Lounge that you should not pooh-pooh, because this is where all the nicer booze is. But the Diamond Club kicker is access to the glass-walled, mosaic-tiled Mermaid Pool.

Off-Site: Try to make it over to the coast of Bavaro to soak up the surf vibe and hop on a catamaran for a few hours. You can snorkel in the Cortesito Reef and relax in the natural pools. These are party boats, so bring a fit liver.

Rate: $$$

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Vibe: Designed by French firm AW2 with the international jet-set circuit in mind, the minimalist 43-suite, nine-villa Silversands is a sea of tranquility, its blond wood, neutral tones and pale marble buoyed by exquisite furniture from Spanish architect Patricia Urquiola.

Rooms: The Silversands rooms are done in neutral-toned glam—oatmeal is the new oatmeal—and lots of vertical wooden slats shooting up walls and camouflaging the cupboards and closets. The seating areas are so inviting you may actually spend time sitting in them. I fell asleep on a giant chaise longue on the balcony (with earplugs to mute all the birds), which is something I never do.

THINGS TO DO: IN GRENADA
TASTE TO TRY: GRENADA GASTRONOMY

F&B: There’s a wine cellar with 1,000 bottles in it. Is this big? I don’t know, but it sounds like I want to drink all of it. Breakfast at Asiatique is stellar—do not skip this. In the evening, it pumps out Modern Thai underneath huge, curlicued wooden ceiling installations. At the beachside Grenadian Grill, we sipped rosé and lunched on salmon tartare and French fries—it was two hours of heaven. Having rum nightcaps under the canopies of the beachfront lounge, we miraculously blended in with the jet-set crowd grooving to the DJ, but really, anyone can fit in here and have a good time and not feel intimidated by the rather posh peeps.

Extras: The Silversands Spa offers locally inspired treatments, sauna, hammam and private pool, plus a tricked-out fitness centre. With a rum and cigar lounge (which seems kinda ’90s to me), the resort is destined for the society pages.

Off-Site: With few high rises and less development, Grenada still manages to possess the kind of charm that appears slightly manufactured elsewhere. Do the hikes up rainforest mountains and find time to book an afternoon on a wooden boat sailing. Make sure you eat the chocolate; it will be the freshest you will ever taste. Prime scuba diving at the Underwater Sculpture Park is well worth it, even if you’re snorkelling.

Word Googled While Writing This: Curlicue

Rate: $$$$

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