Which Country is Best for Your First International Trip? (Caribbean Islands)

If you’re craving a tropical vacation full of sun, sand, and surf, then look no further than the Caribbean Islands. Blessed with soft white sands and translucently blue waters, the Caribbean is the perfect destination for sports enthusiasts and beachgoers alike. But how do you choose where to go amongst 700 islands? Which place is safe and easy for foreign travelers to visit? And what is there to do on each of the islands?

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Hey there, fellow adventurers! If you’re looking to escape the humidity, you’re in for a treat! I’ve put together an article revealing the 4 Least Humid Caribbean Islands that I’ve discovered on my journeys – you won’t believe how refreshing the air feels. And if you’re curious about luxury destinations, don’t miss my piece on the 5 Most Expensive Caribbean Islands – these are the places where we can all dream of indulging in ultimate island opulence. Trust me; you won’t want to miss these gems. Happy travels!

What Country is the Best for Your First International Trip?

For your first trip to the Caribbean, we recommend visiting the Dominican Republic, Puerto Rico, the US Virgin Islands, Jamaica, or Barbados. Not only will you find warm weather and picture-perfect beaches, but these destinations also have plenty to offer in terms of historical, cultural, or outdoor attractions. Therefore, they cater to many different types of travelers. 

We’ve handpicked five of our favorite must-see destinations for you to explore during your trip to the Caribbean. So back your bag (and don’t forget the sunscreen), because this will be a memorable vacation you won’t soon forget!

However, each island is unique in its own way. To help you narrow down your search, we’ll share the highlights and attractions of each one. 

The Dominican Republic

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The Dominican Republic is the most visited island in the Caribbean. Located on the island of Hispaniola (which it shares with its neighbor Haiti), the DR is guaranteed to please almost every type of traveler. 

Not only do you have tropical beaches lined with swaying palms, but there are also plenty of lush jungles, scenic mountains, and charming towns to discover.

Situated on the far eastern side of the island is Punta Cana, a resort town that caters specifically to tourists. It’s the second-most popular tourist attraction in all of Latin America, which means it has a well-developed tourist infrastructure. 

There is a nearby airport, dozens of family-friendly resorts, and of course, miles of pristine coastal beaches. You could easily spend your entire vacation in Punta Canta if you wanted.

More adventurous spirits can explore the protected nature parks of Samana Bay (known for humpback whale watching) or Los Haitises National Park (known for its tropical flora and fauna). There are also plenty of touristic activities (guided tours, nature hikes on jungle trails, zipline excursions) in both of these areas.

Puerto Rico

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As a US commonwealth territory of the United States, Puerto Rico is a great option for your first trip to the Caribbean

You’ll find many similarities as you would back home (for example, they use the US dollar), but with a colorful mix of Hispanic and Caribbean culture. And best of all, you don’t need a visa or even a passport to visit!

If you’re here to explore the city, we recommend starting your trip in Old San Juan. Located only 10 minutes from the airport, this charming neighborhood in Puerto Rico’s capital is filled with historic colonial buildings and some of the best cafes and restaurants on the island.

But if you’re here to soak up the sun, Puerto Rico has its fair share of beaches too. Make your way to the west coast and visit Rincon, a paradise for beachgoers and surfers. 

Or you can visit some of the smaller Puerto Rican islands in the archipelago for a more secluded getaway. Culebra and Vieques sit right off the eastern coast and are easily accessible by ferry or water taxi.

The US Virgin Islands

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Similar to Puerto Rico, the US Virgin Islands are also considered territories of the United States. While the archipelago consists of 50 individual islands, most visitors choose to spend time on Saint Croix, Saint John, or Saint Thomas. 

Each island has its own unique personality and vibe, with different attractions for city lovers, history buffs, or beachgoers.

Saint Thomas is the most popular island and the main cruise ship port for the US Virgin Islands. You can expect to find upscale retail shops, buzzy nightlife, and tons of fine dining establishments. 

And while there are stunning beaches and scenic landscapes, many travelers find Saint Thomas to be a little overly commercialized.

On the other hand, Saint Croix is the perfect place to enjoy laid-back island living. It gets the fewest tourists, so you won’t have to fight for a spot at the beach or a table at the local restaurant. Saint John is better suited for nature lovers, as two-thirds of the park is a protected national park.

As such, there are great opportunities for hiking, snorkeling coral reefs, or fishing in many locations around the island. 


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Over the last few decades, Jamaica has transformed into a tourist-friendly destination that attracts vacation lovers from around the world. Like most islands in the Caribbean, Jamaica has plenty of sun-soaked beaches where you can sunbathe or kick back with a cool, refreshing cocktail. 

However, there are also fascinating historical sites as well, which adds to the diversity of activities on the island.

Most travelers chose to base themselves in either Negril, Montego Bay, or Ocho Rios. Negril has some of the best Caribbean islands for beaches, while Montego Bay is a lively resort town with plenty of bars, restaurants, and entertainment options. 

Ocho Rios is a top pick for families, as there are great all-inclusive resorts and fun activities for kids of all ages.

During your trip, it’s worth stopping by Kingston, the bustling capital of Jamaica. Although you won’t find as many beaches here as you would in the other resort areas, it’s still a worthy destination if you want to experience true Jamaican culture. Here, you’ll find many museums, family-run restaurants, and beautiful parks to keep you entertained.


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With postcard-worthy beaches and a multitude of natural attractions to explore, Barbados is a popular island for first-time Caribbean travelers. 

The island is home to adorable guesthouses as well as 5-star resorts, which means you’ll have no problem planning a worthwhile vacation that matches your budget. 

The southern coast of Christ Church is a great place to base yourself for the week. Not only will you find small fishing villages and white sand beaches, but there are also numerous restaurants, bars, and shops in terms of entertainment.

The west coast is a little less crowded, although you’ll still find your fair share of high-end resorts along the coast. 

If you’re hoping to escape the busy beaches, then we recommend basing yourself on the north part of the island. The region is dotted with small fishing villages and secluded beaches and coves that you can explore. 

But for a more rugged and wild adventure, head east. Although you won’t find as many sunbathing beaches, this area is great for adventure sports and surfing

For many people, the Caribbean is paradise on earth. You can spend your days exploring historic cities, snorkeling with marine life, or simply lounging on the beach with a good book. 

While these islands are great choices for first-time travelers, the Caribbean still has many other worthwhile destinations that deserve to be on your bucket list. 

But by now, you hopefully have a better idea of where you want to spend your relaxing (or adventurous) well-deserved vacation!