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”.
Jupiter Kiteboarding wants to help you with your kiteboarding needs. They offer gear, repairs, lessons and general advice. They can also assist with paddle, wake, surf and windsurf lessons and rentals. Call or email them with your questions.
★ Cool factor: Kite Paddle AND Wake! Visit site
Sail and Snorkel in Puerto Rico with Puerto Rico Boat Trips. Sailing in the Caribbean sea to an exotic island will be one of the most amazing adventures you will experience in Puerto Rico. You will enjoy snorkeling on our pristine reefs and relaxing on our catamaran Fun Cat. We offer free lunch, soda and water all day. Beer is provided for a minimal price. When everyone has had their fill of snorkeling we set sail for home port. The return trip is a Fun Cat party filled with music and our very popular rum punch. Book your trip today.
★ Cool factor: Variety of Boats and Destinations Visit site
Coolest Carib promotes Caribbean Islands and their tourist services. Advertisers who benefit the most from our services include car rentals, catamaran tours, kitesurfing schools, water-sports rentals, scuba diving centers, beach resorts, hotels, restaurants, scooter rentals, boating excursions etc. The website is mostly viewed by Caribbean travelers and tourists. For more information about our rates and exposure scope view our advertising page.
★ Cool factor: We place your advertisement on 50+ Caribbean websites Visit site
Up n' Under Watersports. Your Kiteboarding and Freediving specialists in the British Virgin Islands! Up 'n' Under Watersports invites you to explore the beautiful Caribbean Sea both above and below the water here in the British Virgin Islands! Whether it be learning to Kitesurf in clear warm waters, improving your Snorkeling / Free-diving skills on a historical wreck or going with family and friends on a luxury live aboard catamaran adventure to some of nature's best kept secrets we're here to help!
★ Cool factor: Safety comes first Visit site
Drive Green VI. Convert your car or truck to run on propane! Save 45% per gallon in your work or recreational vehicle with a dual fuel propane upgrade that won't void your warranty. Drive Green VI is on the front lines of developing technology, constantly researching and testing new forms of equipment that would work for us here in the Caribbean.
★ Cool factor: Green Technology! Environmental Friendly! Visit site
Fort Lauderdale Kitesurfing Co offers kitesurfing lessons in Pompano, Lauderdale By the Sea, Deerfield and Boca Raton. Kitesurfing is a mixture of paragliding, wakeboarding, surfing and windsurfing, so it appeals to a really large target group. Owner and instructor Graham Goodwin started running kitesurf-instruction courses as early as 1999. He guarantees you a safe start in this amazing sport for the entire family.
★ Cool factor: Free Lessons on every purchase 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.
By Caribbean Blogger | What To Expect When Relocating In The Caribbean A forty-minute flight between two Caribbean islands can put a…
Continue readingCaribbean Blogger | While the Caribbean is often discussed as a single destination, selecting an island requires navigating a highly diverse array…
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.
A Segway tour through Miami Beach's Art Deco Historic District.
★ Cool factor: glide past 1930s pastel architecture without the walk Book here
Get in the water and see Anguilla's reef life up close.
★ Cool factor: reef time included Book here
Skip the logistics and get where you're going in Aruba without a rental car.
★ Cool factor: door-to-door convenience Book here
See more of Cozumel than just the beach — a guided look at the island itself.
★ Cool factor: guided the whole way Book here
Head out from Turks & Caicos for a real shot at reeling in something big.
★ Cool factor: gear and crew included Book here
An hour on a jet ski exploring the coastline around Antigua.
★ Cool factor: 60 minutes on the water 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.
📍 Grenada — The Ultimate Grenada Travel Guide 2025 | Easy Travel Dude
📍 St John — ST JOHN Completely Blew Us Away — U.S. Virgin Islands Paradise 2026
📍 Bonaire — Bonaire, a Wild Paradise in the Southern Caribbean!
📍 Guadeloupe — 2014 Guadeloupe Islands Press presentation
📍 St Kitts — Heart of St. Kitts Foundation: Open Your Heart, Leave a Legacy
📍 Grand Cayman — CAYMAN ISLANDS Travel Guide 2026 - 10 Best Things To Do
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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