Caribbean Island-Hopping Insider’s Guide

What to do and where to stay on nine of our favorite islands.

Rum bars and seafood shacks, music and megayachts and boutique resorts galore. This time of year, we’re ready to drop it all for a splash of sun – and the Caribbean’s top of mind. But in a sea of tempting sands, how to choose between Saint Lucia and Anguilla, Puerto Rico and the Dominican Republic (while steering clear of tourist traps)? We asked nine high-profile locals what their Caribbean islands mean to them, where they take friends, and how travelers can make the most of their next beach break.

Saint Bart’s | Live the Good Life

The Insider: Hervé Brin, founder, Ligne St Barth Skin Care

As soon as you reach Saint Bart’s you are immediately immersed in good vibrations. No one will try to sell you anything or impose a tempo on you. It’s a nice feeling of freedom amid the beauty of the landscapes, the brightness, the cleanliness, the absence of car horns. Maybe that’s why, at one point, the oldest person on earth was an inhabitant of Saint Bart’s (nun Eugenie Blanchard, who lived nearly 115 years). I like the small market in Lorient for its fruits and vegetables from the neighboring islands. The intense smell of freshly picked tropical fruit combined with the market’s spices is like no other and inspires my fragrances. Fishermen sell their catches at the market on Gustavia, where you’re likely to run into anyone from Jimmy Buffett to Roman Abramovich to a local nurse. One of the biggest spectacles of the year is the St Barths Bucket Regatta, held in March. This megayacht race is breathtaking and as formidable as the America’s Cup.

Where to Stay on Saint Bart’s:

• Cheval Blanc St-Barth Isle de France has breezy Jacques Grange-designed interiors.
• Don’t miss the see-and-be-seen vibe at Oetker Collection’s Eden Rock – St Barths.
• Hotel Le Toiny’s standalone villa suites have their own private heated pools.
• Treat yourself to La Mer spa services at Le Barthélemy Hotel & Spa.
• Le Sereno’s rebuild introduced waterfront suites and an expanded spa.
• The island’s best kids’ club is at Rosewood Le Guanahani St. Barth.
• St. Barth Properties’ 265 villas dot prime hillsides, providing complete privacy.
• Cuvée’s four Saint Bart’s villas feature infinity pools and sleep 10 to 12 guests.

On January 31, 2021, France closed the borders for leisure travel on all of its overseas territories, including Saint Bart’s. The Saint Bart’s government hope to share a reopening date soon. Check with your Virtuoso travel advisor for the latest updates. 

Saint Lucia | Connect with Nature

The Insider: Shala Monroque, creative director, fashion and art consultant

Saint Lucia is an island where nature’s wonders never cease: While driving, you turn a corner and right there is a brilliant rainbow arching over an aptly named flamboyant tree (also known as royal poinciana). For divers, Soufrière Bay at the base of Petit Piton, is spectacular: On a calm day, there’s a mirror reflection of the piton rising straight up from the ocean. Coral juts out at you like trees in the water below. When I lived in New York, I kept returning home to Saint Lucia because it felt more human to me. I’d buy coconuts from the same vendor and he’d bring me gifts of food. At Latille Falls, Selai, a Rastaman, has tended a garden around the waterfall for more than 20 years; he offers a fish pedicure that’s more like fish tickling your feet – which translates into forgetting all your worries. You have no choice but to laugh. And I love Gros Islet’s Irie Bar, a remarkably chill and unpretentious spot where Andy, the owner, serves cold beers and rum with fish from his daily catch – with soothing reggae or film screenings in the background.

A tip when flying out: Check in three hours prior to departure as suggested– which is totally not necessary, as the airport is never that busy – then head back out to Island Breeze Bar & Grill on Vieux Fort’s Sandy Beach, across from the airport. I like to think of it as the coolest airport lounge, and will sit there and have a Piton beer or two. You can even go for a swim; the terminal is literally a two-minute drive away. 

Where to Stay on Saint Lucia:

• Stay at BodyHoliday for an all-inclusive wellness escape.
• For access to a secluded beach, check into Cap Maison Resort & Spa.
• Jade Mountain has suites without a fourth wall, bringing you closer to the lush landscape.
• Settle in at a prime perch between the two Pitons at Ladera Resort.
• Sugar Beach, a Viceroy Resort tempts guests with indulgent treatments in its treehouse spa.

Travelers visiting Saint Lucia must have proof of a negative Covid-19 test taken no more than five days prior to their arrival.

Charlotte Amalie, the capital of the U.S. Virgin Islands.Robert Harding/Alamy

U.S. Virgin Islands | A Diver’s Dream

The Insider: Arnoldo Falcoff, owner, Patagon Dive Center

Even if the typical marine life is quite similar across the Caribbean, the diversity of diving sites around Saint Thomas is remarkable. From ancient coral reefs that grew steadily for centuries to giant granite boulders and from tunnel and canyon formations to the numerous shipwrecks, the visual impact is amazing. Boating and cruising past some of Saint Thomas’ neighboring islands provides constant visual pleasure. Large schools of silversides blanket the coastlines of Thatch, Congo, and Carval keys during the summer. Jacks, bonitos, tarpon, and other predators feast incessantly on these tiny fish, and are one of my favorite underwater sights.

Saint Thomas’ sheltered deep-water harbor made it a big colonial trading center. Main Street’s fancy shops are partitioned from the old days’ large warehouses – their original walls still show the many coral chunks used as bricks. The capital, Charlotte Amalie, is an extended relic of Danish colonial architecture with much to explore: the original house of impressionist Camille Pissarro; the old Danish fort, which was renovated years ago and turned into a museum; and the Pirates Treasure Museum’s antiques, shipwreck artifacts, and exhibits. After seeing the town, take the gondola to Paradise Point, at the top of a high hill, for the best view of the city and the harbor.

Where to Stay in the U.S. Virgin Islands:

• Take to the water on The Ritz-Carlton, St. Thomas’ 60-foot catamaran, The Lady Lynsey II.
• Villas of Distinction’s 50 U.S. Virgin Islands properties range from two-bedroom hideaways to ten-bedroom estates.

Travelers visiting the U.S. Virgin Islands must have proof of a negative Covid-19 test taken no more than five days prior to their arrival, or they can present a positive antibody result received within the past four months. Because the islands are a U.S. territory, U.S. travelers do not have to present a negative Covid-19 test to return to the mainland U.S.

Turks and Caicos | Make a Splash

The Insider: Karel Rodney, manager, Da Conch Shack

It feels like everyone knows everyone in the Turks and Caicos, even if they’re not related. Providenciales – “Provo,” as it’s called – is my favorite island and is the most developed. Da Conch Shack, located in beautiful Blue Hills, is Provo’s most established beach restaurant and rum bar; locals head there to dine with their toes in the sand beneath palm trees, listening to the waves while drinking the “Jan” rum punch. Of course, we’re world-famous for our beaches: Everybody goes to Grace Bay Beach for its shopping, restaurants, bars, and pristine beach – I run 10K there every morning; quieter Long Bay Beach is windy and popular with kite surfers; Sapodilla Beach, on the Caribbean side, has powdery white sand and calm waters ideal for Jet Skiing. If you love water sports, as I do, you can do everything here from parasailing to deep-sea fishing, diving, or chartering a yacht to island-hop. On days off, I often take a boat to North Caicos. It’s more popular with locals because it’s way less busy than Provo – it’s our quiet getaway, relaxing on the beach or visiting the caves. “Gontanort,” you say, with an island flair.

Where to Stay in the Turks and Caicos:

• Slip off to Como Parrot Cay for private island bliss.
• Amanyara has serene Indonesian vibes transplanted to the Caribbean.
• Book a palatial private villa at Grace Bay Club’s Estate, a resort within the resort.
• Treat yourself to the mother-of-pearl scrub at The Palms Turks and Caicos’ 25,000-square-foot spa.
• Escape crowds at The Shore Club, set on a secluded stretch of Long Bay Beach.
• Wymara Resort & Villas features chic, minimalist design.

Travelers visiting the Turks and Caicos must have proof of a negative Covid-19 test taken no more than five days prior to their arrival.

Encuentro Beach near Cabarete has the DR ’s most consistent surf.Nina Choi

Dominican Republic | Let the Rhythm Move You

The Insider: Isaac Hernandez, musician

Dominicans’ Spanish-African heritage distinguishes us in terms of music and food, as well as in our strong and recognizable accent and dialect. Music and dancing are an important part of our culture. Santo Domingo’s live scene centers around the Zona Colonial’s bars and theaters, such as Casa de Teatro. Some of our most famous artists – Juan Luis Guerra, Luis Días – performed here when being introduced in the scene; it’s a loved and respected art house.

Every Sunday at the historic Ruinas de San Francisco, the band Grupo Bonyé plays merengue, bachata, and son. People of all ages from different places gather to enjoy it – it’s a thing, as they’ve performed there every week for more than 12 years, sharing their happy, festive vibe. La Espiral 313 celebrates our roots music, which came from Africa and became our folkloric music. Outside Santo Domingo, Santiago de los Caballeros is the second most important city in the country. It’s well known for merengue típico, the oldest style of the rhythm, and is home to some of our most talented musicians.

Where to Stay in the Dominican Republic:

• Eden Roc Cap Cana’s La Furnia is a natural cenote at the heart of the resort.
• Amanera makes an impression with its clifftop infinity pool overlooking Playa Grande.
• Test your polo skills at Casa de Campo Resort & Villas’ equestrian center.
• Casa Colonial Beach & Spa is a restored colonial estate on the island’s less-developed north shore.
• Splurge at Tortuga Bay Puntacana Resort & Club’s expansive Oscar de la Renta boutique.

Travelers visiting the Dominican Republic do not need proof of a negative Covid test to enter the country. Airports will perform random tests and mandatory temperature checks.

British Virgin Islands | Embrace Island Chic 

The Insider: Kristin Frazer, fashion designer and founder, Trèfle Designs 

Whether I’m island-hopping or simply taking a scenic drive, the colors that nature provides in our flowers, trees, fruits, and animals always stand out. There’s no better inspiration for me than the British Virgin Islands. Take one of our most serene beaches: Smuggler’s Cove. When driving here on the western end of Tortola, along the Sir Francis Drake Channel, the ocean is about ten feet away – that’s what I call living in true paradise. The private road to Smuggler’s Cove can be rugged, but when you arrive, it’s the way nature intended.

Coming into Zion Hill and just before reaching Apple Bay, there’s a mural that depicts a little of the West End culture and its people; my late great-grandmother “Ms. Becca” is highlighted, which is inspirational in itself. Nearby, on Carrot Bay, I often head to D’CoalPot for ice-cold passion fruit juice or lemonade, along with its unmatched conch chowder and grilled lobster. The view serves as my canvas, and the sound of the waves never gets old. I have a soft spot in my heart for these places, which find their way into my collections’ bold prints that are rooted in western Tortola’s less touristy villages and untouched, natural shoreline. They’re tranquil, but full of life.

Where to Stay in the British Virgin Islands:

• The open-air Rum Room at Rosewood Little Dix Bay has more than 100 rare bottles from around the globe.
• Retreat to Moskito Island for a memorable family reunion.
• Necker Island is a sustainable private island paradise, complete with flamingos and lemurs.

Travelers visiting the British Virgin Islands must have proof of a negative Covid-19 test taken no more than five days prior to their arrival. All travelers are required to test again on arrival and quarantine for four days before being tested again. Once that test returns negative, travelers are free to move within the territory.

Annandale Falls outside Saint George’s on Grenada.Robert Harding/Alamy

Grenada | Unwind Like an Olympian

The Insider: Kirani James, two-time Olympic gold medal sprinter, Tokyo 2021 competitor

You can always find something to do in Grenada. Saint George’s is fantastic; it’s the capital and is where everything happens. When I’m home on vacation I always make sure to visit Market Square to stock up on spices – it’s one of my favorite things to do because it’s always a vibrant place. Nearby, the House of Chocolate has a café and small museum about the history of chocolate on the island, and will let you make your own cocoa balls. The island’s food in general will surprise you. Weekly Fish Fridays in my hometown of Gouyave are very lively, with steel pan music or live shows. Kelly’s Hot Spot is a local favorite for fresh seafood from the nearby fish market. In Sauteurs, Petite Anse serves fantastic barbecue with a wonderful view of some of the smaller islands from its balcony.

If you like nature, visit Annandale or Concord waterfalls. They’re secluded and very calming – if you’re lucky, you might see a monkey. Wherever you go, you’ll discover that the country’s most positive attribute is our people: We are very down-to-earth, very laid-back and friendly.

Where to Stay on Grenada:

• Plan for a romantic meal at Calabash Luxury Boutique Hotel’s vine-draped, fine-dining restaurant, Rhodes.
• Silversands Grenada boasts the longest pool in the Caribbean.
• For the choicest spot on Grand Anse Beach, stay at Spice Island Beach Resort.

Travelers visiting Grenada must have proof of a negative Covid-19 test taken no more than three days prior to their arrival. All travelers are required to quarantine upon arrival in a government-approved facility for four days before being tested again.

Puerto Rico | Taste of Place

The Insider: Juan José Cuevas, head of culinary operations, Condado Vanderbilt Hotel

Puerto Rico is famous because of our beaches, natural reserves such as El Yunque and Caja de Muertos, the old city’s colonial architecture, bioluminescent bays, and music. But also for soul food. Our cuisine is distinguished by its abundance of flavorful meaty, crunchy, and fish dishes, with a healthy dose of herbs and spices. It’s the kind of food you want to devour. Agritourism activities are a great way to connect with the island, such as a visit to Hacienda Tres Ángeles in Adjuntas, a hidden gem with beautiful views and even better coffee. Learning about this part of our culture, with a cup of coffee in hand, is a fantastic way to spend a day. It’s not far from Ponce, and a great day trip from the popular southern city.

Piñones’ coast in the north connects metro San Juan to the town of Loíza, which is the epicenter of Afro-Puerto Rican culture. It’s more rustic than San Juan, and much smaller, with incredible ocean views. Locals come here on weekends for a chinchorreo, a gathering of friends that may turn into a bit of a road trip, stopping to eat and drink along the way. Kiosko El Boricua and Carmín are among the most famous beachside shacks, known for fried staples such as bacalaitos (a pancakeshaped cod fritter), sorullitos (a delicious mix of cornmeal and cheese), and the crowdpleasing alcapurrias (mashed cassava with taro root, green plantain, and crab or beef). This is the way we grow up – sharing family time around food.

Where to Stay in Puerto Rico:

• Don’t miss the Condado Vanderbilt Hotel’s historic pink-marble art deco lobby.
• Dorado Beach, a Ritz-Carlton Reserve has a great water-sports program and outdoor activities on its 1,400 acres.
• Post up at Fairmont El San Juan Hotel for its proximity to downtown and its perch on Isla Verde Beach.
• In the heart of Old San Juan, Hotel El Convento occupies a cheery yellow seventeenth-century convent building.
• The Ritz-Carlton, San Juan is set on a two-mile stretch of beach 20 minutes east of Old San Juan.
• Tee off on The St. Regis Bahia Beach Resort, Puerto Rico’s Robert Trent Jones Jr.-designed golf course.

Travelers visiting Puerto Rico do not need proof of a negative Covid test to enter the territory.

Roadside repast on Anguilla.Richard James Taylor

Anguilla | Sail Into the Sunset

The Insider: David Carty, Rebel Marine owner, boat designer and builder

What’s special about Anguilla is its sense of freedom and intimacy that 15,000 people share. It’s easy to know everybody; there’s a familiarity and an egalitarian feel. We have a stunningly beautiful marine environment and beaches, and we get a nice sea breeze most of the year. I try to swim at Rendezvous Beach every day if I can – I like the angle of the wind coming off the sea in my face.

For boating, Prickly Pear Cays and Dog Island are my special places – undeveloped, just as they were a couple of hundred, if not a couple of thousand, years ago. I love that. Locals come here with a cooler and swim ashore to hang out for a few hours, then get on their boats and head back to Anguilla. The sea breaking over the reefs on Prickly Pear is magical.

Anguilla’s national sport, boat racing, was born of poverty. Because of our country’s aridity and lack of arable soil, we were never a successful plantation economy, so we relied more on the sea. As a result, we have this remarkable marine heritage and are competitive when it comes to sailing. If two boats come alongside, you can bet your bottom dollar a race will start. That’s fueled the competition and the sport ever since, and there’s no better time to witness it than on Anguilla Day, May 30, when we race right around the island. Sandy Ground is the best vantage spot, because all of the big races finish there. People line the beach and cliffs for a really cool bird’s-eye view over the harbor.

Where to Stay on Anguilla:

• Belmond Cap Juluca’s whitewashed, Moroccan-inspired domed villas brighten moods on sight.
• Taste your way from Tokyo to Morocco to Greece and beyond at CuisinArt Golf Resort & Spa’s five restaurants and bars.
• Four Seasons Resort and Residences Anguilla’s glamorous interiors come courtesy of design maven Kelly Wearstler.
• Spread out at Malliouhana’s 25 oceanfront acres.
• Book a museum-style escape to Quintessence Hotel Anguilla, an intimate mansion hotel with a lauded art collection.

Travelers visiting Anguilla must receive permission from the island prior to visiting, must have proof of a negative Covid-19 test taken no more than five days prior to their arrival, and must quarantine for at least ten days upon arrival.

Article Credit: Virtuoso