They’re historic, but they’re not about the years. They’re elegant, but they’re not just about luxury. These hotels aren’t fixed in time — they transcend time. They’re places that, at one point or another, crystallized their view of the perfect Caribbean hotel experience. And they work even better today than they did at the beginning. These are the Caribbean’s timeless hotels — the places that take you to an experience far beyond the ordinary.
The Horned Dorset Primavera — Puerto Rico
The initial idea for this article came about while an editor was sitting in the bar at this magnificent boutique property on the edge of Rincon in Puerto Rico. From the exquisite Moroccan furnishings to the aforementioned bar, filled with rare books and rarer service, this is the essence of a timeless Caribbean hotel.
Round Hill — Jamaica
It’s no surprise that Ralph Lauren, one of the world’s experts on timeless things, designed the rooms here (and owns two villas, too). This is a throwback to the Caribbean glamour of yore: think afternoon tea, actual keys and impeccable service (and a dreamy, old-fashioned bar). A magical place.
Graycliff — Bahamas
An evening at the lounge at Graycliff quickly finds its way to the top of your list of great memories. In a single room, Graycliff has captured a signature moment: a jazz singer at the piano; champagne cocktails and old cognacs; warm service; fresh-rolled cigars and an overwhelmingly happy energy. The latter is something that extends across this boutique hotel property.
Jamaica Inn — Jamaica
The ideal of the West Indian hotel: elegant, with almost 70 years of family-owned passion that’s palpable inside its walls. It has that perfect pace, the thing you feel as you leisurely walk around its grounds (and private beach).
Belmond La Samanna — St Martin
It begins with an almost endless, magnificent beach. But this hotel is the epitome of the French Caribbean hotel: a white-hued, Mediterranean-style retreat wrapped in Gallic flair and elegance. Oh, and marvelous food.
Sandy Lane — Barbados
When you think of the perfect hotel in Barbados, you think of Sandy Lane. A stately, regal property, this has always been the beacon of luxury on the island — and its charms transcend the changes of the calendar.
Montpelier Plantation and Beach — Nevis
There are more than 300 years of history here, still alive in the sugar mills and the untouched green hills. This boutique property has managed to pull off a challenge: to delicately inject modern sensibility and amenities into a centuries-old property.
One and Only Ocean Club — Bahamas
There is an almost impossible tranquility here; the kind you only find at those rarest of retreats in the region. It is a hotel that celebrates beauty in all its forms, whether the natural wonder of Cabbage Beach or the terraced gardens modeled on Versailles. The latter create one of the most magnificent views anywhere in the hemisphere.
Half Moon — Jamaica
This is a grand place, a reminder of why Jamaica has long been such a romantic place for so many travelers, from the graceful rooms to the perfectly tailored bars to the Sugar Mill restaurant. A true Caribbean classic.
Hostal Nicolas de Ovando — Dominican Republic
This charming hotel is located in the Colonial Zone of Santo Domingo, more than 500 years pulsing through the old walls. It’s a wonderful marriage of preservation and function, a hotel that reminds you of a long-lost era without stranding you there.