The Cool List: The Caribbean’s Coolest Places to Stay in 2025, From Adventure Resorts to Historic Inns 

It was one of the first major guides we at Caribbean Journal ever put together: The Cool List, whose first edition was back in 2013 and which remains an unrivaled curation of unique, character-filled, personality-driven, artful hotels around the Caribbean.

Every year, it’s a bit different, with one unifying theme: The Cool List is all about hotels that are different. These aren’t traditional hotels, they’re almost always on the smaller side, and they’re all oozing with personality and a human touch. Because while there are great large resorts across the Caribbean, it’s in the smaller properties that you really get a sense of place, where the artistry of the hotelier can truly manifest itself (with some exceptions, of course). That’s where you find the cool.

As always, this list is the result of our unmatched, on-the-ground research and stays across the Caribbean, with choices by our editors based on the hotels we all fell in love with over the course of the year and beyond. To be clear, this isn’t the best hotels in the Caribbean. It’s the Cool List, a collection of unique, diverse hospitality concepts that are all defined by, well, being indefinable. It’s a list of places many of which you probably haven’t heard of. If you love the authentic Caribbean, they’re places you need to see.

Our 2025 Cool List takes you across the wider Caribbean Basin, from an adventurous luxury hotel in Panama to a colorful boutique hotel in St Thomas to a far-off retreat in a secret corner of the Turks and Caicos Islands. 

Los Establos Boutique Resort, Panama Travelers want something more these days. Yes, they want luxury and comfort, great food and warm service. But they want more. They want experiences. And at this fantastic boutique resort set on a stunning hillside in Panama, adventure is in their DNA. Every day of your stay, you can take a free tour or excursion every day of your stay, whether it’s an immersive journey into the art of coffee production, a thrilling zip line or white-water rafting. Los Establos, the sister resort to Antigua’s Hammock Cove, is, simply put, the Caribbean Basin’s new bucket-list hotel.