We Asked 10 Travel Experts Their Favorite Island Destination—and They All Said the Same Thing

There’s no such thing as a bad time for an island getaway. Across the globe, there are tiny, floating plots of land just waiting for you to come to dig your toes in the sand, swim in the azure waters, and kick back to relax and do nothing at all. However, according to the travel experts we spoke to, there are a few islands that shine a little brighter than the rest. And it turns out, they all agree that the Caribbean is the best place to find them. Since there are hundreds of islands dotting the Caribbean Sea, we’ve whittled down their selections to the top spots to make your island vacation planning a little easier. 

St. Barts

The ultra luxurious island of St. Barts seemed to be on the tip of every travel expert’s tongue thanks to its French-Caribbean charm and consistently excellent service.

“St. Barts blends sophistication with simplicity. One day, you might be enjoying dinner at a chic beach club, and the next, you are grabbing a fresh sandwich from Petite Colombier, the little island bakery everyone adores,” Allison Collier, owner of Collier Travel Collective, shared. “For evenings, Le Tamarin is pure magic, set in a tropical garden. It feels like stepping into another world.” For places to stay, Collier said that Eden Rock is “a true gem,” while Cheval Blanc is “elegant and romantic on Flamands Beach, also the best spot for a little body surfing.”

Kaleigh Kirkpatrick, the founder of The Shameless Tourist, agreed that St. Barts is an ideal getaway thanks to its “17 postcard-perfect beaches on a tiny island that you can loop in under an hour, “plus refined French-Caribbean dining, beach clubs, chic hotels, and great shopping.” She added, “It’s easy to mix lazy beach days with celebratory dinners—and the service culture is consistently excellent.”

According to Andrew Satkowiak of The Luxury Travel Agency, the perks go beyond the beaches as “the whole island feels like the south of France. With it being a French property, it’s no surprise that the majority of the workers there are French.” Need a spot to eat? “One of my favorite places for a long leisurely lunch is at Shellona. Spending time at their beach beforehand is highly recommended if you enjoy people watching.” 

Tobago

Another island that gets a lot of love is Tobago, praised by our experts for its unspoiled nature and affordable vibe.

“Tobago is the Caribbean’s best-kept secret, where turquoise waters, untamed rainforest, and a refreshingly laid-back island vibe come together at an incredibly reasonable price,” Kendra Guild, a vice president at Solos, said. “Whether you’re snorkeling the coral tropical reefs of Buccoo, savoring a beachside bake and shark, or dancing to steelpan rhythms under the stars, this island delivers an experience as authentic as it is affordable.” 

For Rosalyn Acosta of Live Heal Travel, it’s Tobago’s nature tourism opportunities that make it unforgettable. “For me, the most profound experience Tobago offers is witnessing the nesting of the giant Leatherback sea turtles,” she told T+L. “From March to September, these magnificent creatures, some weighing over 1,500 pounds, return to the beaches where they were born. Watching a mother turtle haul herself ashore under a canopy of stars to lay her eggs is a truly primal and humbling sight.” 

Anguilla

Looking for a more boutique-forward energy? These experts say Anguilla is the island for you. 

“It’s my favorite tropical island I’ve visited because it has stunning white beaches, turquoise water, and small crowds,” Amber Haggerty of Amber Everywhere, explained. “Anguilla is a little hard to get to, so it’s easy to find your own quiet stretch of shoreline if you go looking for it.”  

Jason Wright, owner of Paradise Weddings, agreed, adding that “Anguilla is super laid-back, so no cruise ships, no big crowds, just silky beaches and cozy boutique resorts. The water’s ridiculously blue, and it’s perfect if you want peace, quiet, and amazing seafood.” Wright noted that it can be a bit pricey, “but worth every cent for how serene it is.”

More Caribbean Favorites

While these three certainly got the most love, travel experts couldn’t help but to call out other favorites for you to consider. 

Jamaica: “Jamaica offers something for everyone, whether it’s a family trip, girls or guys trip, honeymoon, wellness/spiritual mission, or even a solo trip,” Ebonee Brown, founder of Flying In Color, said. “It’s also perfect for all budgets, offering vast natural beauty, a vibrant culture, and a plethora of activities for all ages.”

Turks & Caicos: “You’ve got incredible people who are warm and friendly. The Turks islanders treat you like you’re one of them,” Nikheel Advani, COO of Grace Bay Resorts, shared. “To add to that, it’s one of the most beautiful destinations in the world. You have these powder-white sands with almost nobody on them and 50 shades of turquoise water. And there are 40 different islands; many people don’t realize it’s not just one destination. You can get a boat and visit South Caicos, which is the fishing island, or Providenciales, which is the island where most of our resorts are. I encourage visitors to take a boat and go see all these islands and to go diving.” 

Puerto Rico: “Puerto Rico has so much culture, so when our clients ask us for a Caribbean island that doesn’t feel like they could be on any beach, anywhere in the world, it’s our top suggestion,” Heather Christopher, owner of HC Travel Firm, said. “The music (Bad Bunny!!), the beaches, being able to go mountain biking on the same day you hang out at the beach, the random German restaurant sitting on top of the mountains, hiking trails to caves and gorges off the side of the road. It’s a place where you want a car and a sense of adventure.” 

Saint Lucia: “For romantics and the slightly adventurous, we recommend Saint Lucia,” Wright noted. “It has The Pitons (those two dramatic mountains you see in all the postcards), an absolute stunner. If you stay near Soufrière or at one of the southern beaches like Sugar Beach, you’re basically waking up in a dream. There’s hiking if you’re into that, or you can just hop on a catamaran and take in the views with a drink in hand. Very honeymoon vibes.”