These 20 Caribbean Resorts Give You a Luxury Summer Vacation With a Boutique Personality
O:LV Fifty Five, Puerto Rico
Not every great Caribbean summer needs sand between your toes, and O:LV Fifty Five is the proof. This adults-only, design-forward boutique hotel sits between the calm Condado Lagoon and the buzzing streets of San Juan’s Condado district, in the heart of Puerto Rico’s most stylish neighborhood. Its 26 sleek suites lean hard into striking contemporary design, with marble bathrooms, Frette linens and a city-cool sensibility courtesy of the team behind the award-winning O:live brand. The rooftop is the real scene-stealer: an infinity pool gazing out over the lagoon and skyline, plus a bar with a DJ booth built into a converted Rolls-Royce.
The restaurant turns out inventive Caribbean-Asian plates, and the whole place trades beachy mellow for genuine swagger. Summer in San Juan means warm nights, great music and Old World streets to wander, all just steps from your door. It’s romantic, a little rebellious, and refreshingly different from the usual resort template. Come here when you want your island escape with a pulse.
Guy Britton is the managing editor of Caribbean Journal. With more than four decades of experience traveling the Caribbean, he is one of the world's foremost experts covering the region.
