Do you Speak Caribbean?
Mark Twain once said that twenty years from now, you’ll be more disappointed by the things you didn’t do than by the ones you did do.
So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails.
This time of year — honestly, anytime — I’m ready to drop everything and dive into silky water and powdered-sugar sand.
Rum bars, seafood shacks, beach shanties, calypso music, salty pirates, sweaty dance floors, megayachts, and boutique resorts galore...
The Caribbean islands are top of mind and should absolutely be at the top of your list.
Here are some favorite islands — and the protocols for getting there.
Unlike the steady weather, travel protocols change constantly, so while the information below reflects current guidance, when you’re ready to go, utilize this Virtuoso Travel Advisor for the latest restrictions and liberations. You’ll be glad you did.
U.S. Virgin Islands
Travelers visiting the U.S. Virgin Islands must present proof of a negative Covid-19 test taken no more than five days prior to arrival. Because the islands are a U.S. territory, American travelers do not need a negative test to return to the mainland.
My home away from home, the USVI is permanently seared into my heart.
Fair winds, blue skies, secluded beaches, off-shore reefs, national parks, underwater monuments, hiking trails, petroglyphs, strong-willed locals, and even stronger drinks...
I learned to sail these waters with a true pirate and comrade and lived, laughed, and loved well on these emerald volcanic rocks.
St. John remains one of the most beautiful places in the world and an absolute diver’s paradise.
Where to stay in the U.S. Virgin Islands:
Take to the water aboard The Ritz-Carlton, St. Thomas’ 60-foot catamaran, Lady Lynsey II, to Honeymoon Beach.
Villas of Distinction in Peter Bay, St. John, for unforgettable sunsets and chef-prepared meals.
My personal favorite: a St. Thomas yacht charter with Moorings.
With year-round balmy seas and fair winds, plus access to more than 50 surrounding cays and islets, there may be no better Caribbean vacation. The turquoise water and island culture are meant to be explored by boat.
Seven- to ten-day itineraries available.
Puerto Rico
Travelers visiting Puerto Rico do not need proof of a negative Covid test but must complete a Travel Safe Questionnaire before arrival.
Puerto Rico was our stomping ground for real nightlife.
Load up the Veuve Clicquot and repeat after me: beaches, massage, steam, shake... repeat.
But beyond the nightlife, the island offers natural reserves like El Yunque and Caja de Muertos, Old San Juan’s colonial architecture, glowing bioluminescent bays, and music everywhere you turn.
If I had to choose one favorite thing about Puerto Rico, it would be the soul food.
The cuisine bursts with herbs, spices, fresh seafood, crunchy textures, and deeply flavorful dishes rooted in local tradition.
While the memory of some massages may be fading, the vivid memories of Puerto Rico and its people certainly are not.
Puerto Rico is incredibly accessible right now and ready to welcome travelers with open arms.
Where to stay in Puerto Rico:
Don’t miss the historic pink-marble Art Deco lobby at Condado Vanderbilt Hotel.
Dorado Beach, a Ritz-Carlton Reserve, offers exceptional outdoor adventures and water sports across 1,400 acres.
Fairmont El San Juan Hotel is perfectly positioned near downtown and Isla Verde Beach.
The Ritz-Carlton, San Juan sits on a beautiful two-mile stretch of sand east of Old San Juan.
Tee off at The St. Regis Bahia Beach Resort’s Robert Trent Jones Jr.-designed golf course.
Dominican Republic
Travelers visiting the Dominican Republic do not currently need proof of a negative Covid test to enter.
I am so glad the DR is back — and thriving.
The Dominican Republic deserves every bit of the acclaim it receives.
Its Spanish-African heritage shines through in the music, food, language, and unmistakable rhythm of life.
Music and dancing are woven deeply into the culture.
And wouldn’t you know it? I’ll be there in a few weeks to dance, dance, and dance some more. Squeal.
Where to stay in the Dominican Republic:
Eden Roc Cap Cana’s La Furnia cenote is a hidden natural gem.
Amanera stuns with its clifftop infinity pool overlooking Playa Grande.
Test your polo skills at Casa de Campo Resort & Villas’ equestrian center.
Indulge in all-inclusive luxury at Hyatt Zilara Cap Cana.
Turks and Caicos
Travelers visiting Turks and Caicos must provide proof of a negative Covid-19 test taken within five days of arrival.
Of course, Turks and Caicos is famous for its sugar-soft beaches.
Everyone gravitates toward Grace Bay Beach for its restaurants, shopping, bars, and pristine shoreline. I spent seven glorious days there in January and already plan to return.
But quieter Long Bay Beach attracts kite surfers with its steady breeze, while Sapodilla Beach offers calm waters and powdery sand ideal for relaxing.
If you love water sports as much as I do, this is paradise.
Parasailing, fishing, diving, yacht charters, island hopping...
And there’s truly nothing like sinking your feet into the sand at the Conch Shack and Rum Bar after a day diving the reef.
Take me back.
Where to stay in Turks and Caicos:
COMO Parrot Cay for private-island bliss.
Amanyara for serene Indonesian-inspired luxury in the Caribbean.
Grace Bay Club’s Estate villas for expansive privacy.
The Palms Turks and Caicos for its stunning 25,000-square-foot spa.
The Shore Club for a quieter escape on Long Bay Beach.
Saint Lucia
Travelers visiting Saint Lucia must provide proof of a negative Covid-19 test taken within five days of arrival.
Saint Lucia is an emerald island where nature never stops showing off.
As you wind through switchbacks and mountain roads, you’ll suddenly round a corner and find a brilliant rainbow arching across a flamboyant tree.
For divers, Soufrière Bay at the base of Petit Piton is extraordinary.
On calm days, the reflection of the Pitons on the water feels almost surreal, while coral formations rise below like underwater forests and reggae drifts softly through the warm Caribbean air.
Flights continue to increase, and I even have a contact for helicopter transfers straight from the airport.
Where to stay in Saint Lucia:
BodyHoliday for a wellness-focused all-inclusive retreat.
Cap Maison Resort & Spa for secluded beach access.
Jade Mountain for its iconic open-air suites.
Ladera Resort for unmatched Piton views.
Sugar Beach, a Viceroy Resort, for indulgent treehouse spa treatments.
Anguilla
Travelers visiting Anguilla must receive pre-approval from the island, provide proof of a negative Covid-19 test taken within five days of arrival, and quarantine for at least ten days upon entry.
I almost didn’t include this delicious island because the restrictions remain strict.
But if you have the time and flexibility, Anguilla is absolutely worth fighting for.
For boating lovers, Prickly Pear Cays and Dog Island are pure magic — undeveloped, untouched, and breathtaking.
Locals load coolers onto boats, anchor offshore, swim in, spend the day, then sail home at sunset.
The waves breaking across the reefs at Prickly Pear are mesmerizing, and the water feels almost unreal.
Where to stay in Anguilla:
Belmond Cap Juluca for its dreamy Moroccan-inspired villas.
CuisinArt Golf Resort & Spa for incredible global dining.
Four Seasons Resort and Residences Anguilla for glamorous Kelly Wearstler-designed interiors.
Malliouhana for its expansive oceanfront setting.
How Far Adventures is an independent affiliate of GTN, a Virtuoso Member.
I love traveling through the Caribbean and indulging in all its beauty — and I love travel planning just as much.
If you’re curious about another culture and ready to dive in, I would love to help you get there.
