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”.
Star Island Tours Star Island Tours. They're a family owned tour agency who knows the island inside out. They understand that you are on Sint Maarten for a short time and want to see as much as possible. So they have devised these three tours that will give you great value for money. All three tours include scenic routes and key landmarks of the island.
★ Cool factor: They customize tours to suit your time frame and cost! Visit site
PR Half Mile. is much more than a car event. It brings together owners of exotic cars and "supercars" to race a half-mile on an airstrip in a unique and elegant environment. The "Puerto Rico Half Mile Event" is recognized like the most prestigious exotic car racing event in Puerto Rico. It is most of the times open to the general public who will have the opportunity to enjoy and be part of this spectacular event.
★ Cool factor: Lamborginis against Porsches against Audis. Cool! Visit site
Heart of St. Kitts is driven by of a coalition of local businesses committed to sustainability. The Foundation acts to build awareness around sustainability priorities in St. Kitts and provide funding for local projects that make the island a better and more sustainable place to live and experience. Through support from local tourism businesses and visitors to the island, the Heart of St. Kitts Foundation aims to inspire better stewardship of the environment, culture and lasting legacy of St. Kitts.
★ Cool factor: Conserve land and marine habitat Visit site
Aruba. Their white-sand beaches, cooling trade winds and warm, friendly people are just a few reasons why so many people return to Aruba year after year. It's a very happy island!
★ Cool factor: It's the happy island! Visit site
Fischer's Cove Beach Hotel is a beautiful Caribbean beach side setting. An intimate beach side property on the southwestern side of Virgin Gorda, BVI, that overlooks Sir Francis Drakes Channel. Enjoy a tranquil quarter mile, bohio studded, white sand beach lapped by turquoise waters in the British Virgin Islands.
★ Cool factor: On the beach! Visit site
Electric Stand-Up Scooter Rentals Say hello to your portable ride for quick island exploration between Havensight docks and downtown Charlotte Amalie in Saint Thomas, US Virgin Islands. The most efficient way to cruise the sidewalks. Your sleek, speedy island companion. Hop on, zip around, and make the most of your island getaway.
★ Cool factor: The quickest way to zip to downtown 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 readingBy Caribbean Blogger | Going Beyond the Port. Many of us are guilty of stepping off our cruise ship on port days…
Continue readingBy Caribbean Blogger | How to Have a Multi-Country Adventure. Traveling around the Caribbean can be an amazing experience. But the differences…
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Continue readingBy Caribbean Travel Blogger | Moving to the Caribbean can feel like a dream come true. Between the turquoise waters, laid-back lifestyle,…
Continue readingBy Gloria Martinez | How to Stay Comfortable, Safe, and Energized The Caribbean promises warm beaches, vivid sunsets, and cultural charm that feels…
Continue readingBy Gloria Martinez | Planning a surprise trip for someone you love is one part logistics, two parts theater. It’s the rush…
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.
Grab your gear and explore St. Thomas's coastline on your own schedule.
★ Cool factor: flexible — no set schedule Book here
Time it right and watch the sky turn pink over Grand Cayman from the water.
★ Cool factor: golden-hour views Book here
See more of St. Martin than just the beach — a guided look at the island itself.
★ Cool factor: guided the whole way Book hereA week-long guided dive trip exploring Grenada's reefs and wrecks, including the Bianca C.
★ Cool factor: dive one of the Caribbean's largest shipwrecks, the Bianca C Book here
A tasting experience built around unexpected local flavor pairings, guided by a Martinique food expert.
★ Cool factor: unexpected flavor pairings picked by a local food expert Book here
See more of Grand Cayman 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.
📍 Virgin Gorda — Virgin Gorda BVI | Things To Do | Calming Aesthetic | Tropical Travel 4K
📍 Curacao — Discover Curacao 4K Island Guide Curacao Trailer
📍 Bahamas — Behold the Islands of the Bahamas!
📍 Guadeloupe — 2014 Guadeloupe Islands Press presentation
📍 Turks and Caicos — TURKS & CAICOS: Most COMPLETE Travel Guide • 55 Do's and Don'ts (+ Maps/Food) [2025]
📍 St Martin — St Maarten Tourism Bureau - 50th Years Carnival Promo video
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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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