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Browse all Caribbean tours by selecting your preferred island above.
Each tour is independently operated. Once you book, you'll receive the operator's contact info and tour details right away. Here are some tours you can book right now. Enjoy your adventure!
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CoolestCarib opens the door to the Caribbean’s rhythm and color. Wander through our handpicked islands and the experiences they offer. Let our travel stories guide your getaway, and share your island experiences with the world @CoolestCarib.
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Island Hopping the Caribbean and Beyond
By Caribbean Blogger | How to Have a Multi-Country Adventure. Traveling around the Caribbean can be an amazing experience. But the differences between locations matter. When traveling between Caribbean islands, you may have to cross international borders, even when the distance appears short on the map. It can be tricky. For example, you have Barbados, …
Top 5 Caribbean Destinations for Digital Nomads
By Caribbean Blogger | Caribbean destinations for digital nomads continue to draw professionals who want stable workdays paired with outdoor recovery time. Because the climate remains warm year-round, daily routines do not change with the seasons. At the same time, aligning with the North American time zone keeps collaboration simple and predictable. Together, these conditions …
Continue reading "Top 5 Caribbean Destinations for Digital Nomads"
How to Ship Your Belongings to the Caribbean
By Caribbean Travel Blogger | Moving to the Caribbean can feel like a dream come true. Between the turquoise waters, laid-back lifestyle, and warm tropical breeze, it’s easy to imagine yourself relaxing on the beach after unpacking your last box. However, before that happens, there’s a big task to handle – figuring out how to …
Continue reading "How to Ship Your Belongings to the Caribbean"
Caribbean Travel Tips for Seniors:
By Gloria Martinez | How to Stay Comfortable, Safe, and Energized The Caribbean promises warm beaches, vivid sunsets, and cultural charm that feels like medicine for the soul. But for senior travelers, a trip to paradise also requires practical planning – because relaxing doesn’t mean letting your guard down. From managing mobility to avoiding dehydration, a …
How to Plan a Surprise Trip for Your Partner That Actually Feels Magical!
By Gloria Martinez | Planning a surprise trip for someone you love is one part logistics, two parts theater. It’s the rush of secrecy paired with the hope that the effort will land as joy, not chaos. But pulling it off isn’t just about booking flights and hiding confirmations – it’s about timing, subtle cues, …
Continue reading "How to Plan a Surprise Trip for Your Partner That Actually Feels Magical!"
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Caribbean Videos
Caribbean Services
St. Martin
B52 Kitesurfing School is located on the French side, at the Flamboyant Village on the Baie Nettle Lagoon. They specialize in kitesurfing and foiling lessons and rentals. No wind, no worries, go foiling behind a boat. It's like water sking, just better cause you hover above the water on a surfboard. Very cool!
The Cool Factor:
Personal one-on-one lessons - very cool!
Virgin Gorda - BVI
Fischer's Cove Beach Hotel is a beautiful Caribbean beach side setting. An intimate beach side property on the southwestern side of Virgin Gorda, BVI, that overlooks Sir Francis Drakes Channel. Enjoy a tranquil quarter mile, bohio studded, white sand beach lapped by turquoise waters in the British Virgin Islands.
The Cool Factor:
On the beach!
Puerto Rico
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.
The Cool Factor:
Many locations in Puerto Rico
St. Thomas & St. John - USVI
Carib Solar Tech is based in St. Thomas, U.S. Virgin Islands. We design, sell and deploy solar heating systems ranging from residential heating to commercial heating, direct and indirect pool/spa heating and heat recovery systems. Our team members have 25+ years as active solar thermal rebate dealers and installers participating in the local V.I. Energy Office Rebate Program.
The Cool Factor:
Preserve the environments of the Caribbean islands
Martinique
Baz Notik is located at Hotel Carayou in La Pointe du Bout, Les Trois-Ilets. This water sports center offers water sports rentals and lessons of a big variety like kitesurf, windsurf and wakeboard. The location is amazing. You can either launch from site and go upwind (if you're at that level), or they take you out (up-wind) by boat and you kite back at your leisure. If you're in Martinique by cruise ship take the 20 minute ferry to Pointe du Bout, which is also a hidden gem, a petit village with many bistros and boutiques.
The Cool Factor:
It's windy most of the time on location.
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Caribbean Tips
Best holiday deals in the Caribbean are between June and September. It's off season, so expect really really good deals in terms of accommodation, car rentals and boating trips. Don't be shy to ask companies whether they're running specials. Also follow CoolestCarib on social media for specials. We're on Facebook, Twitter, Instagram and Tumblr.
Tips by Liz Strauss, an experienced traveler and piano entertainer. www.lizpiano.com [Disclosure]
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About CoolestCarib Network
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 your tours & activites and browse the articles on Caribbean vacation plans. We also champion Caribbean businesses, offering a comprehensive package in revealing their services to Caribbean tourists.
Our website showcases the following on every island page:
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