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”.
JimBOATtrips.com offers boat trips, sailing snorkeling and fishing excursions on a great variey of yachts in and around Puerto Rico, Culebra, Vieques and Spanish Virgins.
★ Cool factor: Variety of boats & variety of islands! Visit site
The Jamaica Environment Trust (JET) has a small and vibrant team. They were formed in 1991 by a group of citizens concerned about the state of Jamaica's natural environment. They are a non-profit, non-governmental membership organization based in the Kingston and St. Andrew area, but their projects are implemented all over the island.
★ Cool factor: Jamaica's longest running environmental education program. 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
Make the most of your vacation to the Virgin Islands! No matter what kind of adventure you're looking for, there's something for everyone to enjoy! Choose from private boat charters, snorkeling trips, night kayak tours and more. Their Night See-Through Kayak Biolumiscent Tour is a feature not to be missed. Choose from our carefully selected list of island tour operators for your one-of-a-kind Virgin Islands adventure!
★ Cool factor: Biggest variety of water sports on St. Thomas Visit site
Fiberworx is Aruba's number one surfshop. If you ever need any kind of mountain bike, board, sail, kite, or need to pimp up your gear, Fiberworx is the place to get it. They will help you choose the best product and give you professional advice about all our products.
★ Cool factor: They can pimp up your ride 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.
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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.
A guided hike up Gros Piton, one of St. Lucia's iconic UNESCO-listed twin volcanic peaks.
★ Cool factor: summit a UNESCO World Heritage peak Book here
Reserve a beach chair ahead of time and skip the scramble for a spot.
★ Cool factor: guaranteed beach seating Book here
A guided rainforest hike followed by a stop at Luquillo's famous roadside food kiosks.
★ Cool factor: the only tropical rainforest in the U.S. National Forest System Book here
Grab your gear and explore St. Martin's coastline on your own schedule.
★ Cool factor: flexible — no set schedule Book hereA traditional bamboo raft trip down the calm Martha Brae River, guided by a local raft captain.
★ Cool factor: a slow bamboo-raft float steered by a local captain Book hereA guided climb up Jamaica's famous terraced waterfall, followed by beach time at Margaritaville.
★ Cool factor: climb one of the Caribbean's most famous waterfalls 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 Martin — Saint Martin & Sint Maarten Travel Guide (2026) | Best Beaches, Adventures & Island Tips
📍 Grand Cayman — Fall Only In Cayman | Vacation Your Way
📍 Martinique — Best Things To Do in Martinique 2026 4K
📍 Cozumel — Aprendiendo a bucear! Cozumel #1
📍 Antigua and Barbuda — Paradise Awaits You in Antigua and Barbuda
📍 Turks and Caicos — Turks and Caicos 2019
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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