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
Virgin Port Services is the premier port agency in the US Virgin Islands. Their professional and knowledgeable staff provides exceptional service to Cruise Ships and Yachts.
★ Cool factor: The owner is an avid tennis player. Visit site
Sky Banditz is a full service Kiteboard Center with longtime Owner and Chief Instructor Francisco Escudero. Their School is located at the prime spot for Kitesurfing and Paddleboarding in San Juan and Rio Grande. They offer one to one or group instruction for novices to expert level advanced instruction. Skybanditz kitesurfing lessons and programs will allow you to learn the way you want to, by respecting your progression rhythm and allowing you to find a lesson best adapted to you. You can choose different time formats, from one hour up to several days.
★ Cool factor: Many locations in Puerto Rico 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
St. Croix Tours and Activities Visitors can explore historic sites like Christiansted National Historic Site, dive into the island's marine life with snorkeling and scuba diving excursions at Buck Island Reef National Monument, or immerse themselves in local culture through lively festivals and culinary tours. Adventurers can enjoy kayaking through serene mangroves, hiking through lush rainforests, or simply relaxing on picturesque beaches with crystal-clear waters. Whether you're seeking history, adventure, or relaxation, St. Croix has something to offer every traveler.
★ Cool factor: All tours can be booked online! Visit site
VIP Adventure arrange tours or rentals of paddleboard, kayak, snorkeling, bicycle, inline skate, skateboard or jetski. Our concept is based on three important aspects: outstanding experience: unique activities, human and nature relation and the best personalized service to create your best tour experience in Puerto Rico. We provide a selection of adventures catalog, so you can book the adventure that you are looking! From the beautiful San Juan to the amazing eastern coast Fajardo and the exclusive islands of Palomino or Icacos. Our excellent service will fulfill your personal, corporate and residential lifestyle needs. We are well known to personalize your adventure and corporate event and make it the best experience out there!
★ Cool factor: Many activities many locations! 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 fly fishing charter targeting bonefish and tarpon in St. John's flats.
★ Cool factor: sight-fish bonefish on the flats Book here
A popular, highly-rated excursion in Jamaica, ready to book directly.
★ Cool factor: highly rated by travelers 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 here
A guided hike through El Yunque National Forest paired with an evening bioluminescent bay excursion.
★ Cool factor: rainforest by day, glowing water by night Book hereA boat safari on the Black River to spot crocodiles and birdlife, paired with a visit to YS Falls.
★ Cool factor: spot wild crocodiles from a safari boat Book hereA guided kayak tour out to Peanut Island near Riviera Beach, with optional snorkeling.
★ Cool factor: a man-made island with its own snorkeling reef 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.
📍 Bonaire — Bonaire: The Sustainable Destination
📍 Bahamas — I Went to Bahamas for the Food!!
📍 Puerto Rico — Visit Puerto Rico! Dream Vacations
📍 Curacao — Feel it for yourself in Curaçao
📍 Florida — The Power of a Florida Vacation
📍 Turks and Caicos — Grand Turk Travel Guide-Turks and Caicos Islands-4K
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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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