The short version
The six Caribbean hotels I book most right now, island by island: Secret Bay in Dominica, Jumby Bay off Antigua, Amanyara in Turks and Caicos, Barbuda Belle, Baoase in Curacao, and Palm Heights on Grand Cayman. Each one is here for a different kind of trip.
People ask me for “the Caribbean” like it’s one place. It isn’t. A rainforest cliff in Dominica and a design hotel on Seven Mile Beach have almost nothing in common except warm water, and the whole job of a good advisor is knowing which one is actually yours.
So this isn’t a ranking. It’s the six hotels I book most right now, one per island, each here for a specific kind of traveler. When I say favorite, I mean it in the literal sense: these are the ones I’d send my own family to, and the ones I keep going back to myself.
If you want the Forbes-rated set specifically, I broke those out in the best Forbes Five-Star hotels in the Caribbean. This list is different — it’s personal.
Dominica: Secret Bay
Dominica isn’t a beach island, and that’s the point. It’s rainforest, rivers, and volcanic coastline, and Secret Bay sits on a forested clifftop above two small beaches on the northwest coast near Portsmouth. The villas are essentially private treehouses in wood and glass, each with its own plunge pool and a dedicated villa host who handles everything from breakfast to boat trips.

It’s a Relais & Châteaux property, and it’s the one I send couples to when they want privacy over a scene. Ask for one of the newer Ti-Fey villas out toward the cliff edge — the sea drops away beneath you and you’ll barely see another guest all week.
Antigua: Jumby Bay Island
Two miles off Antigua, reachable only by the resort’s own boat, Jumby Bay is a private island with no cars — just bikes, beaches, and a lot of green. Oetker Collection took it over from Rosewood, and it now runs all-inclusive, which on a private island means you stop thinking about money by about day two.

There are cottages, villas, and a handful of private estates. For families I book an Ocean Cottage with a plunge pool a few steps from the sand; for couples, one of the beachside suites. If a private island is the whole assignment, it also earns a place on my list of the best private-island resorts in the world.
Turks and Caicos: Amanyara
Amanyara is the quietest hotel on this list. It’s out on the Northwest Point of Providenciales, backed by an 18,000-acre nature reserve, with timber-shingled pavilions set around dark reflecting ponds and one of the best house reefs in the region a short swim off the beach.

It skews adult, serene, and design-obsessed in the way every Aman is. Book an Ocean Pavilion if you want the water in front of you, a Pond Pavilion if you want the calm. Turks and Caicos technically sits in the Atlantic, but for a barefoot-Aman week it belongs firmly in this conversation.
Barbuda: Barbuda Belle
Barbuda is Antigua’s wilder sister island — pale-sand beaches, a famous frigate bird colony, and almost no development. Barbuda Belle is a tiny beachfront hotel: a handful of timber bungalows on an empty stretch of sand, run more like a private home than a resort.

There’s no scene, no crowd, barely any signal — that’s the draw. It closes through the late-summer and fall storm months, so this is a December-to-June play. I book it for people who’ve done the big-name Caribbean resorts and want something that feels like the edge of the map.
Curacao: Baoase Luxury Resort
Curacao is the island people forget, and I love it for a specific reason: it sits in the southern Caribbean, largely below the hurricane belt, so it’s my answer when someone wants the region in late summer or early fall and the rest of it looks dicey.

Baoase is a small, family-run resort on a private lagoon-style beach just outside Willemstad — 23 rooms, suites, and villas done in a Balinese style, twelve of them with private plunge pools. Book a beachfront villa with a plunge pool, and eat at the beach restaurant more than once.
Grand Cayman: Palm Heights
Palm Heights is the outlier here — a design hotel, not a hideaway. It’s a 52-suite, all-suite property on Seven Mile Beach with a 1970s-Riviera look, yellow umbrellas down on the sand, a serious food-and-drink program, and a crowd that came to be seen a little.

Grand Cayman is easy to reach from the U.S. and dead simple to travel — good roads, great diving, no friction. I book Palm Heights for design-minded travelers, first-timers who want the Caribbean without a long-haul, and anyone who likes their beach with a bit of a scene. Get an ocean-view suite high enough to catch the sunset.
So Which Caribbean Island Is Right for You?
Short version, because this is the question I actually get asked. Want nature and total privacy? Secret Bay or Barbuda Belle. Want a car-free private island with the kids? Jumby Bay. Want barefoot, adults-first calm? Amanyara. Traveling in hurricane season and want to lower the odds? Curacao and Baoase. Want easy, stylish, and close to home? Palm Heights. If the pool is the whole point, most of these also turn up in the best hotel pools in the world.
What You Actually Want to Know
Which of these is best for a first Caribbean trip? Palm Heights on Grand Cayman or Jumby Bay off Antigua. Both are easy to reach from the U.S., simple to get around, and hard to get wrong.
Where should I go during hurricane season? The Atlantic hurricane season runs roughly June through November. Curacao sits in the southern Caribbean, largely below the main storm belt, which is exactly why I lean on Baoase for late-summer and fall trips.
Which is best for a honeymoon? Secret Bay in Dominica for privacy and drama, or Amanyara in Turks and Caicos if you want serene, design-led, and adult. You won’t be tripping over families at either.
Are these all beach resorts? No — and that’s deliberate. Secret Bay is a rainforest-cliff property with small beaches below, not a wide-sand resort. The other five are on the water, in very different moods.
Tell me which of these sounds like your kind of trip and I’ll build the whole thing around it — the flights, the right villa, the transfers, the small parts that go sideways when no one’s watching. Email me and we’ll start.
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