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”.
Tap And Still has three branches, in Havensight and Redhook in St. Thomas and Cruzbay, St. John. Join them for melt in your mouth smash 1/4 pounders, home made veggie burgers, 1lb hotdogs, wings, tap beer and so much more! They have regular theme night parties, bands and DJs.
★ Cool factor: Best burgers and beers in the US Virgin Islands Visit site
Sunfari VI Jeep Tours. Our philosophy behind our company is to offer tours that are not only personal & private , but affordable as well. At Sunfari we're about making the smallest footprint while still enjoying all of what our beautiful island has to offer you. Sightseeing, hiking, beaches, snorkeling, paddle boards, kayaks & even powerboating. We have it all & will customize your day to exactly how you wish!
★ Cool factor: Mad Max style jeeps 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
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
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
Patagon Scuba Dive Center is a PADI 5-Star Dive Operation. They are celebrating their 20 years in service Their Patagon Dive Centers are located at: Saint Thomas: The Ritz-Carlton, and Saint John: Caneel Bay, A Rosewood Resort Experience the waters of the Virgin Islands "Patagon Style"! Their multilingual staff can instruct SCUBA in English, Spanish, Italian, German, and French. Come enjoy a professional and personalized underwater experience!
★ Cool factor: They operate from a 5 star location! 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 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 guided tour and tasting at Jamaica's oldest continually operating rum estate.
★ Cool factor: taste rum from an estate distilling since 1749 Book hereA guided ghost-hunting tour through Key West's reputedly haunted streets and buildings.
★ Cool factor: Key West is considered one of the most haunted small cities in America Book hereAn aerial tour over St. Lucia's Pitons, rainforest and coastline by helicopter.
★ Cool factor: the Pitons from the air Book here
See more of Dominican Republic than just the beach — a guided look at the island itself.
★ Cool factor: guided the whole way Book here
Head out from Grand Cayman for a real shot at reeling in something big.
★ Cool factor: gear and crew included 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 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.
📍 Guadeloupe — 2014 Guadeloupe Islands Press presentation
📍 Virgin Gorda — Virgin Gorda ,The Baths / British Virgin Islands 4K
📍 Antigua and Barbuda — Top 10 Best Things to Do in Antigua and Barbuda [Antigua and Barbuda Travel Guide 2024]
📍 Grand Cayman — CAYMAN ISLANDS Travel Guide 2026 - 10 Best Things To Do
📍 St Croix — Best Things To Do in St Croix Virgin Islands
📍 Grand Cayman — Fall Only In Cayman | Vacation Your Way
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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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