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”.
EcoRentalsVI.Com is a new electric car rental agency in Saint Thomas US Virgin Islands. In summary: The 1st all environmental friendly car rental, zero emissions, doesn't require oil changes, filters, spark plugs, doesn't need tune ups, no filling up disposal sites. No filling up of dumpster bins with pollutants or waste. No visiting gas stations.
★ Cool factor: Zero Emissions! Visit site
Caribbean Foodservice, Inc., under the direction of Howard Bowring, the company has been in a constant growth mode for the past 25 years. His efforts were recognized by the Small Business Administration by naming him the Small Business Person of the Year in 2009. Our sales staff is experts in the area of wholesale non perishable foods and disposable paper products.
★ Cool factor: Their online specials Visit site
Aruba Active Vacations Windsurfing, landsailing, mountain biking, Stand up Paddle boarding and snorkeling is what Aruba Active Vacations has to offer. If your idea of a good time is a combination of relaxing and actively exploring one of the most exotic corners on earth, you have come to the right place! At Aruba Active Vacations you will find a beach hideout with shade, music, fresh water shower, drinks and the right crew and equipment to have an Active Vacation! www.Aruba-Active-Vacations.com
★ Cool factor: Most affordable rentals in the Caribbean Visit site
Hertz St. Thomas is a locally owned, independent car rental franchisee with the singular goal of providing the 5 star service their customers have come to expect in the beautiful US Virgin Islands. You can take their cars on the ferry to St. John. They have two locations. One in Lindberg and one at airport. They have the latest car models of all kind, and you may rent if you are under 25 years old.
★ Cool factor: You can rent if you're younger than 25 years old. Visit site
St. Kitts Intoxicating natural beauty, sunny skies, warm waters, and white sandy beaches combine to make St. Kitts one of the most seductive spots in the Caribbean. Its strategic location and valuable sugar trade led to an advanced and luxurious development that was among the best in the Colonial Caribbean.
★ Cool factor: More than a quarter of its land is a National Park Visit site
TRES PALMAS, one of the most established surf shops in the Caribbean. Clothing, boards, and everything surf. They're also associated with PRISK surf school. Rumor has it they're working on a website.
★ Cool factor: A surf shop by surfers, what's cooler than that? 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.
Caribbean 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 readingBy Caribbean Blogger | Relocating to the Caribbean is a dream for many, and bringing your car along can make settling into…
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 tour of Nevis's old plantation sites and colonial history, including a ferry crossing from St. Kitts.
★ Cool factor: sister-island history, ferry included Book here
Cover more ground (and coastline) with an extended jet ski run out of Antigua.
★ Cool factor: 90 minutes on the water Book here
See more of Puerto Rico than just the beach — a guided look at the island itself.
★ Cool factor: guided the whole way 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
A popular, highly-rated excursion in Jamaica, ready to book directly.
★ Cool factor: highly rated by travelers 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 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 — St Barth open
📍 St Thomas — TOP 8 Cruise Excursions in ST. THOMAS You WON'T BELIEVE EXIST!
📍 Anguilla — ANGUILLA | ULTIMATE TRAVEL GUIDE | NORTH AMERICA EDITION
📍 Grand Cayman — Fall Only In Cayman | Vacation Your Way
📍 Aruba — Top 10 Things to Do in Aruba | Aruba Travel Guide
📍 St Lucia — St Lucia Tourism Authority
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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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