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”.
Pita Express Delivery is a delightful little deli that delivers. Located on the same premises as Amalia Cafe. In Palm Passage Downtown Charlotte Amalie. They deliver quickly and also cater. Go to PitaExpressVI.com to view their specials and full menu. Also subscribe to their daily specials on their website.
★ Cool factor: Out of town deliveries too. Visit site
Premier Destination Services is the DMC (Destination Managment Company) in St. Thomas and St. John, US Virgin Islands and specializes in service management for corporate groups and incentive groups whether it's group-travel, accommodation or corporate-entertainment. Experience the Best these Caribbean islands have to offer!
★ Cool factor: Serves both St. Thomas and St. John Visit site
E-Foiling Fun Family Adventure Embark on an electrifying aquatic journey with e-foiling, where cutting-edge technology meets the thrill of adventure.
★ Cool factor: The closest to flying without a permit humanly possible! Visit site
Latitude 17 Scuba St. Croix. They specialize in personalized, private PADI dive instruction from Discover Scuba through Divemaster, and guided diving here on beautiful sunny St. Croix, US Virgin Islands. They have great diving year round with water temps from 77 degrees in the winter to 84 degrees in the summer.
★ Cool factor: Year round diving! Visit site
Hommage Hotel & Residence Situated in Terres Basses, this modern and refined hotel of 148 rooms, boasts an exceptional museum garden along with art pieces. The spacious and luminous rooms have a terrace with a view of the lagoon, the gardens or the pool. Beautiful beaches like Baie Rouge, Baie Longue and Baie aux prunes are a few minutes away.
★ Cool factor: Gated, high-end, village resort atmosphere 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 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 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.
See more of Grand Cayman than just the beach — a guided look at the island itself.
★ Cool factor: guided the whole way 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 hereA self-guided electric bike rental for exploring Grenada at your own pace.
★ Cool factor: cover more ground than walking, with none of the climbing effort Book hereA guided sunset kayak paddle along St. John's coastline.
★ Cool factor: sunset from the water, paddling yourself Book hereA bobsled ride through the rainforest canopy above Ocho Rios at Mystic Mountain.
★ Cool factor: bobsled through rainforest canopy, Jamaican-style Book here
The longest jet ski option — two hours to cover the coastline at your own pace.
★ Cool factor: 2 hours 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.
📍 Barbados — Brilliant Barbados Exotic
📍 Bahamas — I Went to Bahamas for the Food!!
📍 Curacao — Discover Curacao 4K Island Guide Curacao Trailer
📍 St Barths — Top 10 Best Things to Do in St. Barts [Saint Barthélemy Travel Guide 2026]
📍 Puerto Rico — Visit Puerto Rico! Dream Vacations
📍 Tortola — British Virgin Islands Travel Guide 2026
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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