I used to gravitate toward Caribbean destinations like The Bahamas for luxury getaways, but a recent trip to St. Thomas and Puerto Rico shifted my perspective. Though some may view the two US territories as casual and accessible, I found that both islands rival the Caribbean’s most coveted luxury destinations — and they come without the hassle of international travel.
Photo: St. Regis Bahia Beach Resort
2 Luxury Caribbean Escapes, No Passport Required
Carrying only a driver’s license as identification, I took a quick four-hour flight from New York to experience two distinct luxury escapes: a couple of nights in laid-back St. Thomas at the island’s Ritz-Carlton, followed by a couple of nights at The St. Regis Bahia Beach Resort in vibrant Puerto Rico. The result was an elegant, exclusive trip that challenged the notion of mass tourism while proving that paradise is closer than you think (and attainable without a passport).
The Ritz-Carlton, St. Thomas
Photo: The Ritz-Carlton, St. Thomas
A scenic 30-minute drive through lush, hilly roads from Cyril E. King Airport leads to The Ritz-Carlton, St. Thomas, the island’s only five-star resort. Upon arrival, the resort feels intimate enough to navigate easily yet expansive enough to offer endless entertainment. With beach access, infinity pools, ocean-view cabanas, a spa, and exclusive access to The Ritz-Carlton’s luxury sailing catamaran, there’s no shortage of ways to unwind and enjoy.
I stayed in a Club Level King Room overlooking the resort and Great Bay’s blue waters. Though I’m not usually a morning person, I found myself waking up at around 6 AM each day just to watch the sunrise from my balcony. My stay included exclusive lounge access and a dedicated concierge service, which was both incredibly helpful and always available.
Photo: The Ritz-Carlton, St. Thomas
Each day began with breakfast at Bleuwater, one of the Ritz-Carlton’s on-site restaurants. The French toast is a standout, but it’s the friendly and attentive staff that really makes the experience special. Every restaurant at the resort offers ocean views, but I’d recommend sitting on the patio to take in the scenery while you dine.
In the evenings, Alloro is a must for dinner. The restaurant specializes in Sicilian cuisine, particularly pasta and pizza. Don’t skip the appetizers, which are often the unsung heroes of the menu, especially the bruschetta and burrata. For my main course at Alloro, I opted for the frutti di mare (linguine pasta with semi-dried tomato, mussels, clams, and shrimp in a flavorful sauce) and extra-moist olive oil cake for a sweet finale.
One of the most unforgettable meals I had at The Ritz-Carlton, St. Thomas, was a private dining experience on the beach, nestled beneath seagrape trees. The journey there set the mood before my group was greeted by a lively performer on stilts, dancing to Caribbean music. In the intimate, candle-lit setting, we savored a four-course tasting menu that included smoked foie gras with local tuna and a showstopping poached Caribbean lobster.
Photo: The Ritz-Carlton, St. Thomas
Dinner by the shore is just one example of the experiences St. Thomas delivers, both on and off The Ritz-Carlton grounds. I kicked off the second day of my visit by carving out time for relaxation, first spending a few hours in one of the resort’s ocean-view cabanas. Though I never did, my inner child wanted to try the water slide nearby — a nice family-friendly touch at a luxurious resort. I also indulged in a rejuvenating massage at the resort’s spa — and learned that The Ritz-Carlton is the only property in St. Thomas that offers ocean-view massages.
When I was ready to balance out the relaxation with some adventure, I took a guided tour of the island. We made a stop at the Yacht Haven Grande marina, where waterfront restaurants, artisan boutiques, and beautiful murals set the tone. Mountain Top, famous for its banana daiquiri and duty-free shopping, was up next. From that vantage point, the view of Magens Bay — a beach hailed as one of the world’s most beautiful — was magical.
Photo: The Ritz-Carlton, St. Thomas
Taking in the view of Magens Bay was incredible, but there’s no better way to fully appreciate the island’s beauty than a sunset sail aboard Lady Lynsey II, The Ritz-Carlton’s exclusive luxury sailing catamaran. This was a highlight of my trip, complete with an open bar and gourmet hors d’oeuvres that paired perfectly with the dusky scenery.
Together, these experiences gave me a picture of St. Thomas, by sea and by land. But just as I was beginning to settle into the rhythm of island life, after two days it was time to move on to another destination — just a quick 45-minute flight away. I boarded a small aircraft, with no more than 10 seats, and in mere moments was soaring from St. Thomas to Puerto Rico.
The St. Regis Bahia Beach Resort
Photo: The St. Regis Bahia Beach Resort
Upon arriving in Río Grande, Puerto Rico, I was off to see another beautiful property: The St. Regis Bahia Beach Resort. There, towering palms and tropical foliage greet you at what was once a coconut plantation and is now a breathtaking sanctuary nestled between the El Yunque Rainforest and the Espíritu Santo River.
The ocean peeks through a large door at the entryway, and welcome drinks await as you step inside. All around, the lush property blends coastal rainforest with direct beachfront access, creating a space where nature’s elegance meets curated luxury. The tranquility is unmatched, and I quickly learned to look forward to the gentle calls of native coquí frogs settling in each night.
My sun-drenched suite was especially restful, opening to ocean views from both the living room and the bedroom. Amenities included a wet bar, a spacious bathroom with a grand tub and rainfall shower, a private outdoor patio, and beach access just steps away. As serene as the setting is, though, the resort also embraces a spirit of celebration, as evidenced by the nightly Champagne sabrage ritual.
Photo: The St. Regis Bahia Beach Resort
Hosted at Casa Grande, the resort’s main building, the ritual involves opening a bottle of Champagne with a sword to celebrate the transition from day to night. I got to dive deeper into the technique during a Champagne sabrage class on my second day at the resort. After successfully popping our bottles, the group enjoyed its Champagne poolside, a lively spot that’s perfect for mingling and meeting new people.
The beach at the resort, where I was often drawn, would have been another ideal place to savor it. But the two-mile-long crescent beach is just one part of the resort’s natural landscape, and I wanted to explore it all, so I joined a nature tour led by Sebastián Mergal from Soul of Bahia. He shared his vast knowledge of the property’s plant and animal life. We also visited the on-site animal shelter where guests have the option to adopt rescued cats and dogs from the island.
Photo: The St. Regis Bahia Beach Resort
Another activity I enjoyed was taking a complimentary bike ride around the resort, followed by a tennis clinic. I had the chance to train with a coach who’s worked with Shakira. (He shared that she plays barefoot, which almost inspired me to try it myself.) Unwinding at the resort’s Iridium Spa was the perfect next stop. While you don’t have to book a massage to enjoy the extensive amenities — such as the sauna, cold plunge pools, and gorgeous garden area — I couldn’t help but be intrigued by the Encanto Rum Massage, an experience I’ll be sure to try next time.
Although I was enchanted by the resort, I did find myself wishing I’d explored more of Puerto Rico beyond the property. If you’re looking to venture out, Old San Juan is about a 40-minute drive away. While that would make for a nice day trip, rest assured that you don’t need to leave the resort for a culinary experience.
Casa Grande is a great place to start, with a breakfast buffet that has a wide selection of both American and Puerto Rican dishes, along with fresh juices and à la carte options. One standout experience I had at Casa Grande was the Bloody Mary tasting, where I compared the traditional American version with the Puerto Rican Encanto Mary. The latter — made with ají picante (a style of hot sauce) and garnished with crushed plantain chips — was a perfect balance of heat and flavor.
Photo: The St. Regis Bahia Beach Resort
For lunch, Seagrapes serves fresh and flavorful food by the pool, complete with reservable cabanas. In the evening, grab cocktails at The St. Regis Bar before dinner at Paros, a refined Mediterranean restaurant that focuses on locally sourced ingredients. If you’re dining in a group, don’t be afraid to share appetizers and main — when I was there, the lobster rice, in particular, came bursting with flavor and in a big enough portion to feed four people.
For a more intimate dining experience, the resort’s outdoor feast is perfect for special occasions like engagements or family gatherings. My group had the pleasure of enjoying a five-course meal by the beach, paired with Laurent Perrier Champagne. The progression was incredible, from fresh Ossetra caviar, lobster, and king crab to a creative twist on Puerto Rican classics with Kurobuta pork belly confit, local pink beans, and calabaza (pumpkin) risotto.
As my journey wrapped up, I relished how seamlessly my time in St. Thomas and Puerto Rico blended sophistication with ease of travel. The Ritz-Carlton and The St. Regis had a lot to do with that — something I’ll definitely keep in mind the next time I’m looking to plan hassle-free but luxurious getaway. 