One directory for the whole Caribbean — 27 islands, handpicked local gems, travel stories, island radio and the kind of tips you only get from people who live here.
Every island opens into its own guide — tours you can book, the top things to do, fun facts, local businesses and live weather.
No islands match that search yet — try another name or clear the box.
Each island page is a living guide you can actually use to plan — and book — your trip, gathered from a network built by people on the ground.
Book experiences directly, island by island.
The must-sees, ranked by locals.
Language, food, geography, history.
Tune in and listen while you browse.
See the destination before you go.
Up-to-the-minute island forecasts.
Real shots and live social updates.
Local initiatives worth supporting.
Island stations, curated for wherever you are right now.
Car rentals, villas, restaurants and tour operators across the islands — each one earns its place with a “Cool Factor”.
Villa Sol Y Luna consists of a beautifully designed 5,200 square feet, luxury 4 bedrooms property with spacious loft and 5 bathrooms, with the the most spectacular views from almost every window in the property as well as a large infinity pool and top of the line, 5 people capacity, hydro-massage hot tub.
★ Cool factor: House and double story cottage with infinity pool between. Visit site
Amalia Café is a delightful open-air restaurant owned and operated by Randolph and Helga Maynard. Located in the cobblestone Palm Passage, this Spanish meson serves a varied selection of Spanish favorites and augmented by daily tapa and entrée specials.
★ Cool factor: A taste of Spain in the Caribbean! Visit site
Plastic Free Cayman They are a team of volunteers passionate about reducing single-use plastic in the beautiful Cayman Islands. They aim to raise awareness to the growing issues surrounding plastic pollution and help others on their plastic-free journey. They began as a grassroots movement in 2017 with monthly clean ups and were awarded a 'Not for Profit Charitable Trust' certificate.
★ Cool factor: Reducing plastic pollution Visit site
The Cozumel Coral Reef Restoration Program has the objective to restore coral reefs, promote research and marine educational programs. If you participate, not only will you learn to scuba, you will get the Coral Reef Restoration diploma and will become a volunteer in the coral restoration efforts in Cozumel.
★ Cool factor: You get to participate! Visit site
BVI. Discovering the beauty of BVI is all about uncovering the unique character of each island in this unspoiled volcanic archipelago. From the culture and history of BVI's four largest islands to the pristine natural splendor of more then 50 smaller isles, every place you drop anchor offers its own special magic.
★ Cool factor: Balmy trade winds year-round Visit site
The Jamaica Environment Trust (JET) has a small and vibrant team. They were formed in 1991 by a group of citizens concerned about the state of Jamaica's natural environment. They are a non-profit, non-governmental membership organization based in the Kingston and St. Andrew area, but their projects are implemented all over the island.
★ Cool factor: Jamaica's longest running environmental education program. Visit siteJoin a network of 70+ Caribbean sites and put your service in front of travellers planning their trip right now.
Thrive in the Caribbean →Practical, lived-in advice from travellers and locals — the stuff that makes a trip go smoothly.
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Continue readingReal excursions, real islands, zero guesswork — the sails, snorkels and lobster lunches worth building a vacation day around, picked for crews with kids in tow.
A guided hike up Gros Piton, one of St. Lucia's iconic UNESCO-listed twin volcanic peaks.
★ Cool factor: summit a UNESCO World Heritage peak Book here
Time it right and watch the sky turn pink over Grand Cayman from the water.
★ Cool factor: golden-hour views Book here
A popular, highly-rated excursion in Jamaica, ready to book directly.
★ Cool factor: highly rated by travelers Book here
Get in the water and see Turks & Caicos's reef life up close.
★ Cool factor: reef time included Book hereA boat safari on the Black River to spot crocodiles and birdlife, paired with a visit to YS Falls.
★ Cool factor: spot wild crocodiles from a safari boat Book here
See more of Cozumel than just the beach — a guided look at the island itself.
★ Cool factor: guided the whole way Book hereCompare flight prices and book direct with the airline.
Tips by Liz Strauss, an experienced traveler and piano entertainer. www.lizpiano.com · Disclosure
See the destination before you go.
📍 Barbados — Baecation to Barbados Vlog | Our Anniversary, Exploring, Fun Nights, Rihanna's Drive + More
📍 Guadeloupe — 2014 Guadeloupe Islands Press presentation
📍 Bahamas — Behold the Islands of the Bahamas!
📍 Anguilla — Best Places in Anguilla | Anguilla Caribbean #anguilla #caribbean #travel
📍 Tortola — Tortola British Virgin Islands
📍 St Barths — Top 10 Best Things to Do in St. Barts [Saint Barthélemy Travel Guide 2026]
Mention us in your posts and stand a chance to be featured here, @CoolestCarib.
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The CoolestCarib Directory is your portal to the enchanting world of the Caribbean Islands and their array of tourist services, spanning a network of over 60 Caribbean tourist websites. At CoolestCarib.com, you can book tours & activities and browse articles on Caribbean vacation planning. We also champion Caribbean businesses, offering a comprehensive package for revealing their services to Caribbean tourists.
Every island page includes:
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