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”.
Saint Martin. Welcome to the French side, the Friendly Island by excellence! Days filled with sunshine, velvet soft nights and breathtaking scenery are only some of the ingredients that create the unique feel and taste that reflect Saint-Martin.
★ Cool factor: We communicate in English and French Visit site
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
Water Action VI Five Epic Water Sports. One Adrenaline Spectrum. Drift into chill vibes with Kayak & SUP, or crank it all the way up with Jet Ski Rentals, E-Foiling, and Flyboarding. Whether you?re here to relax or ready to ride the rush, your perfect water adventure starts now.
★ Cool factor: Walking distance from airport Visit site
Caribbean Permaculture Research Institute educate and empower their students to: grow food, repair land and build community. To find and create a livelihood based on meeting one's own needs, and helping others meet their needs. To create low maintenance, holistic and functional systems to feed, house and provide income.
★ Cool factor: Their regenerative farming practices Visit site
Nissan St. Thomas When drivers, their cars, and their communities are in sync, our world becomes a better place. Discover driving that's smarter, safer, easier, and absolutely thrilling. Visit their dealership in St. Thomas. Did you know Nissan is one of the world's largest electric vehicle manufacturers. They also sell used cars in conjunction with Drive Green VI.
★ Cool factor: They sell new, used and all-electric vehicles Visit site
Mok Properties PR specializes in short term and long term apartment rentals in the Condado (San Juan) tourist area of Puerto Rico. They also have properties for sale. Most properties are on Ashford avenue in Condado, on or very close to the beach. They are all walking distance to restaurants, nightlife and just 10 minutes by car from Old San Juan.
★ Cool factor: Great variety! All affordable! 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 | Most people headed to the Caribbean arrive at the airport with too much. A second pair of shoes…
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…
Continue readingBy Caribbean Blogger | Caribbean destinations for digital nomads continue to draw professionals who want stable workdays paired with outdoor recovery time.…
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.
Skip the logistics and get where you're going in St. Lucia without a rental car.
★ Cool factor: door-to-door convenience Book here
Skip the logistics and get where you're going in Aruba without a rental car.
★ Cool factor: door-to-door convenience Book hereA guided tour and tasting at Jamaica's oldest continually operating rum estate.
★ Cool factor: taste rum from an estate distilling since 1749 Book hereA guided kayak tour out to Peanut Island near Riviera Beach, with optional snorkeling.
★ Cool factor: a man-made island with its own snorkeling reef Book here
Get in the water and see Grand Cayman's reef life up close.
★ Cool factor: reef time included Book hereA Segway tour through Miami Beach's Art Deco Historic District.
★ Cool factor: glide past 1930s pastel architecture without the walk 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.
📍 St Barths — Your Guide To: St. Barths
📍 Antigua and Barbuda — Paradise Awaits You in Antigua and Barbuda
📍 St Barths — 10 Best Things To Do in St Barts
📍 Grand Cayman — Discover Grand Cayman
📍 St Croix — Welcome to St. Croix US Virgin Islands | Where to Stay, Eat, and Play!
📍 Martinique — Martinique, A Call To Fall In Love With
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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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