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”.
Cayman Islands Tennis Club is situated in the South Sound area of Grand Cayman. The Club consists of 6 hard courts and three clay court surfaces. They offer junior and adult programmes. Their after school classes are for children aged 3-15 years. They also offer a temporary membership for those visiting Grand Cayman for a month or less.
★ Cool factor: Monthly memberships Visit site
Flyboard St. Thomas is an independent flyboard operator based at Lindbergh Bay, located close to the airport. Their office is on the beach in front of Emerald Beach Hotel. They are tucked away behind all the kayaks and jetskis. If they're not at the office that does not mean they are closed - they are probably running errands. The best way to get hold of them is to make a booking online and call to confirm. If flyboard is not your thing, but you may fancy a bit of jetskiing contact their friends at jetskivi.com
★ Cool factor: You become Iron Man in minutes Visit site
Budget has been providing the U.S. Virgin Islands with outstanding service for more than 20 years. They have the largest selection of well-maintained vehicles at low, low prices. They also offer mini-lease plans, and quality pre-owned vehicles. With locations all over St. Thomas and St. John, Budget can meet all of your rental needs.
★ Cool factor: $1 500 worth of coupons to every customer. Visit site
Jamaica. If you're looking for a true adventure there's little more memorable, and beautiful, than hiking the Blue Mountains Peaks. From long sandy stretches to crystal clear water and secret coves...
★ Cool factor: Now that's what I call all right. 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
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 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 full-day catamaran cruise along St. Lucia's west coast, with stops for swimming and snorkeling.
★ Cool factor: a full day on the water Book hereA guided e-bike trail tour through Grenada's countryside and coastline.
★ Cool factor: a guided route through spice country most rental cars never reach 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
Head out from Turks & Caicos for a real shot at reeling in something big.
★ Cool factor: gear and crew included Book here
A guided hike to Annaly Bay's dramatic natural tide pools on St. Croix's rugged north shore.
★ Cool factor: natural tide pools carved into the coastline Book here
A guided kayak tour through Salt River Bay National Historical Park and Ecological Preserve.
★ Cool factor: paddle through a National Park and bioluminescent bay in one 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 Thomas — TOP 8 Cruise Excursions in ST. THOMAS You WON'T BELIEVE EXIST!
📍 Grand Cayman — Grand Cayman Stingray City Drone 4K ©
📍 Aruba — Top 10 Things to Do in Aruba | Aruba Travel Guide
📍 Barbados — Barbados Island Guide - travelguru.tv
📍 Grand Cayman — Fall Only In Cayman | Vacation Your Way
📍 Anguilla — Best Places in Anguilla | Anguilla Caribbean #anguilla #caribbean #travel
Mention us in your posts and stand a chance to be featured here, @CoolestCarib.
Get notified every time we post a new guide, gem or travel tip. No spam — just the Caribbean.
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:
Donations keep the Caribbean Directory project running — or just buy us a coffee.
