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As someone who lives out of a suitcase half the year and spends the other half obsessing over our next trip, I get this question all the time: “Where can I spend my money on a Caribbean vacation without feeling trapped in the resort?”
There’s nothing worse than dropping five figures on a luxury getaway, only to realize the area isn’t safe enough to explore.
That completely defeats the purpose of the trip. If I pay a premium, I want the absolute freedom to rent a car, wander around in the dark and really experience the island.
Looking at our recent Traveler Safety Index data, there is a huge gap in the region. Popular Mexican-Caribbean spots such as Cancun and Playa del Carmen score high, but still have a level 2 travel advisory.
The same goes for famous hubs like Punta Cana, Montego Bay and Nassau.
If you really want to splurge and sleep well, you need the peace of mind that comes with a Level 1 advisory from the U.S. Department of State, which means all you need to do is “take normal precautions” AND a high score on our Traveler Safety Index.
I’ve personally spent a lot of time wandering around this region and am obsessed with our safety index data and government advisories, here are the 5 ultra-safe, high-quality Caribbean destinations that I absolutely love and think are totally worth the splurge:
1. Aruba
Safety index score: 98 | Travel advice: level 1
Aruba is the undeniable star of our safety index, scoring a whopping 98, and dominating for a very good reason.
You are safely outside the hurricane belt guaranteed incredibly stable weatherand the tourist infrastructure is virtually bulletproof.
But for me, the splurge here is all about freedom.
You can book a luxury oceanfront suite at Eagle Beach or reserve a private overwater cabana on Renaissance Island, but you’re not stuck there.
My absolute favorite thing to do on the island is rent a Jeep, throw my camera on the passenger seat and spend the day completely off-roading through Arikok National Park capturing the rugged coastline.
When it’s dark, you can walk to luxury restaurants in Palm Beach without worry.
2. Grand Cayman, Cayman Islands
Safety index score: 84 | Travel advice: level 1
Grand Cayman combines its Level 1 status with world-class medical infrastructure and deep-pocketed financial stability.
It is easily one of the safest environments in the entire regionmaking it a huge appeal to luxury travelers.
The experience here is incredibly polished and strongly focused on impeccable service. The ultimate splurge is checking into the expansive Ritz-Carlton or the Kimpton Seafire on Seven Mile Beach, and charter a private catamaran to Stingray City.
Let’s face it: half the reason I travel is the food. Luckily, the culinary scene here is incredible.
You must reserve a table at Blue by Eric Ripert; their menu is an absolute masterpiece of perfectly executed, approachable coastal cuisine.
3. St. Barts (Saint-Barthélemy)
Safety index score: 90 | Travel advice: level 1
St. Barts is the absolute pinnacle of Caribbean exclusivity.
This small French territory has a zero-tolerance policy and serves as a renowned haven for celebrities, executives and world leaders.
I will never forget the first time I arrived here.
The island naturally filters away the enormous crowds because there are absolutely no direct commercial flights. To get here, you’ll need to take a ferry or make a thrilling landing in a private small-plane charter that drops right over a mountaintop.
Once you’re touched, the splurge is effortless. I highly recommend spending your days relaxing in a private cliff-top villa in Pointe Milou, designer shopping on the pristine streets of Gustavia, and enjoying champagne-filled afternoons at Nikki Beach.
4. Anguilla
Safety index score: 91 | Travel advice: level 1
Just a short boat ride away from the busy, overcrowded cruise port of St. Maarten, Anguilla remains remarkably tranquil and completely untouched by the norms of mass tourism.
When I just want to completely disconnect and disappear from the world for a week, this is the premium destination. It was built for travelers who value absolute seclusion and pristine beaches and a loud, chaotic nightlife.
The island is known for its high-end, villa-centric luxury.
Booking an ultra-premium accommodation such as Cap Juluca or the Four Seasons guarantees a private, incredibly tranquil setting with dedicated butler service.
It is the ultimate place to recharge.
5. Barbados
Safety index score: 81 | Travel advice: level 1
While some islands are designed for total isolation, Barbados offers a vibrant, culture-rich luxury experience.
It is specially designed for travelers who want to leave their resort safely and actually mingle with the locals.
The island’s Platinum Coast on the western side is known for its calm, completely clear waters and enormous luxury estates.
The ultimate splurge here is a stay at the legendary Sandy Laneknown for its world-class golf courses, impeccable service and high-profile clientele.
Because the island is so remarkably safe, I like to spend the afternoon confidently exploring the historic capital of Bridgetown, then head out to dine at elite oceanfront restaurants like The Cliff.
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