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Caribbean Tours

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!

Ultimate San Juan Discovery Private Full Day Experience from Ponce

Puerto Rico Book Now

Bayaguana Runners

Monte Plata Province
Dominican Republic Book Now

Culebra Snorkeling Tour

Puerto Rico Book Now

Timeless Echoes & Legendary Spirits: Private 5 Hr Historic Old San Juan tour, backstage tour at Barrilito Rum Distillery and cocktails

Puerto Rico Book Now

Snorkeling @ Rainbow Reef

The Bahamas Book Now

Rastafari Indigenous Village Experiences

Jamaica Book Now

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#CoolestCarib @CoolestCarib

CoolestCarib is Passionately Caribbean!

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.

On this page, immerse yourself in Caribbean culture with 1. Caribbean Tours, 2. Radio Stations, 3. Articles, 4. Videos, 5.Featured Services, 6.Photography 7. Daily Tips.

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Caribbean Radio Hits!

CAYMAN ISLANDS

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Caribbean Articles

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Caribbean

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 …

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Caribbean General

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 …

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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 …

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International

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, …

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Caribbean

Moving Your Car to the Caribbean: What You Need to Know

By Caribbean Blogger | Relocating to the Caribbean is a dream for many, and bringing your car along can make settling into island life even smoother. Whether you are moving for work, retirement, or simply seeking a change of scenery, having your vehicle with you offers freedom and convenience in a new environment. However, shipping …

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Caribbean Videos

Caribbean Services

St. Thomas - USVI

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!

The Cool Factor:

Mad Max style jeeps

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St. Thomas - USVI

JetskiVI.com. Explore historic Charlotte Amalie Bay. Cruise around Water Island. See stunning Honey Moon Beach. Go on tours or freestyle rides.

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Island Tours on Jetskis!

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St. Croix - USVI

St. Croix Environmental Their mission is to promote the conservation of environmental resources, provide education and advocate for environmentally responsible actions that benefit St. Croix. Their members are their strength. Benefits of membership include free or reduced admission to regular events, leatherback sea turtle watches, discounts in their SEA shop, and - most important - the knowledge that you are supporting and helping with a vital effort to protect our island environment.

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Education Conservation Advocacy

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USVI (United States Virgin Islands)

US Virgin Islands Each of our three major islands has a unique character all its own. St. Croix's Danish influence is perfect for visitors who prefer a laid-back experience. Two-thirds of St. John is a national park. Its comfortable pace is perfect for enjoying the island's world-renowned beaches. St. Thomas boasts one of the most beautiful harbors in the world. As the most visited port in the Caribbean, downtown Charlotte Amalie offers elegant dining, exciting nightlife, duty-free shopping and even submarine rides.

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No passports required for US citizens

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Puerto Rico

Sail and Snorkel in Puerto Rico with Puerto Rico Boat Trips. Sailing in the Caribbean sea to an exotic island will be one of the most amazing adventures you will experience in Puerto Rico. You will enjoy snorkeling on our pristine reefs and relaxing on our catamaran Fun Cat. We offer free lunch, soda and water all day. Beer is provided for a minimal price. When everyone has had their fill of snorkeling we set sail for home port. The return trip is a Fun Cat party filled with music and our very popular rum punch. Book your trip today.

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Variety of Boats and Destinations

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Caribbean Photos

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Caribbean Tips

Sunscreen. No reason to risk looking like a lobster, but the organic type, or the coral reef friendly. Read the label.

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: