Caribbean Luxury Travel

I'm a certified Cayman Islands specialist, with training that includes the islands' weddings and romance track, and I've done an industry training day with Cayman Airways and the island's resort partners. Here's what I tell clients.

Grand Cayman is an easy island. It's just over an hour's flight from Miami, the water is calm, and the food is the reason a lot of people go. The Cayman Islands have more than 200 restaurants, and Cayman Cookout brings big-name chefs to the Ritz-Carlton every January.

Where you stay changes the whole trip. Seven Mile Beach on the west coast has the restaurants and the calm water, and the trade winds have kept it clear of the sargassum that reached the south coast in 2025 and 2026. Wyndham Reef Resort is Grand Cayman's best-known all-inclusive. That's perfect if you want to snorkel off the beach and stay put. It's a long drive to dinner if you don't.

For divers this is serious country. Bob Soto opened the Caribbean's first dive operation on Grand Cayman in 1957, and there are 365 moored dive sites across the three islands. On Little Cayman, Bloody Bay Wall is the one divers plan whole trips around.

What I actually brief clients on is more practical. Leave any ammunition at home, even a spent casing on a keychain or in a piece of jewelry, because it's illegal there and it can get you arrested. And if you're adding Little Cayman, know that there's no hospital on the island.

Want the full picture before you decide? My Grand Cayman Planning Guide walks through every part of the island, the sargassum question coast by coast, and where I'd put you.

June through November is the season, and September is the peak of it. Rates drop for a reason. I book that window when the trip is flexible and the client understands the tradeoff, and I put insurance on it every time. If you have one week a year and it can't move, I'll steer you to January through April and tell you what it costs.

This is a real shape, not a brochure. Seven nights, two properties, one travel day in the middle that doesn't eat the trip.

1. Day 1

   Arrive UVF, drive south

   Fly into Hewanorra rather than Castries so the transfer runs toward Soufrière instead of across the island. The drive from Hewanorra to Soufrière is short but winding, and I'll have your transfer waiting. Dinner at the hotel the first night, always. Nobody makes a good decision after a travel day.

2. Days 2 to 3

   Soufrière and the Pitons

   Sulphur Springs early, before the buses. The mud bath is worth doing once and it will ruin a swimsuit. Afternoon on the water with a private captain out to Anse Cochon, which beats the group catamaran by a wide margin for what it costs.

3. Day 4

   Nothing

   I build one of these into every week. No transfer, no reservation, no guide waiting. It's the day people tell me about later.

4. Days 5 to 6

   Move north to Rodney Bay

   A short helicopter hop or a driver up the west coast, depending on budget and stomach. The north end gives you restaurants outside the resort, Pigeon Island, and a beach that's easier to swim off than the volcanic sand down south.

5. Day 7

   Home

   Late checkout arranged in advance, day room if the flight is evening. Transfers timed to the actual airport, not the closer one.

Caribbean rolls up into a bigger pillar of my planning work. Caribbean and Mexico luxury travel has the wider view, and the journal has the notes I write between trips.