Americans are spoiled by the Caribbean’s proximity.
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Having some of the world’s most unspoiled, vibrant tropical islands within reach is a travel blessing—especially for those who live in the Southeast or nearby. Within a few hours, you can find yourself stepping off a plane in paradise.
There’s just one catch: the Caribbean is home to over 7,000 islands, home to 13 different sovereign nations, along with a slew of dependent territories that are ruled by overseas nations.
In short, it’s a clear win for travelers, but planning a trip might be a little more complex than many think. Along with finding the right island for your vacation needs, you also need to consider things like culture, language, and even nationality.
Some Caribbean islands are easier to visit than others, after all.
And if you want to keep absolutely simple, I suggest visiting one of the Caribbean islands that don’t require a passport. You’ve got two territories to explore across six gorgeous islands. Here’s where to go, where to stay, and what you can’t miss as you visit the US Virgin Islands and Puerto Rico.
Caribbean islands that don’t require a passport: Puerto Rico
Puerto Rico
A large tropical island that offers you a bit of everything, from Latino culture to lush jungles to endless urban adventures in the capital of San Juan. A little Spanish will help you make connections and uncover hidden gems, but no need to bring your passport along.
How can you get there?
The majority of travelers arrive in San Juan, then stay a few nights in the capital before heading to an all-inclusive resort. Another popular international hub is Rafael Hernandez Airport in Aguadilla, which takes you a bit further away from the city hustle and closer to more remote resorts and experiences.
Where should you stay?
- San Juan Marriott Resort & Stellaris Casino is a popular stop in San Juan because the hotel is affordable, comfortable, and is home to one of the city’s most popular casinos.
- Wyndham Grand Rio Mar Rainforest Beach and Golf Resort is popular because it’s located in a lush jungle setting in the Rio Grande area. It’s the perfect spot to take on exotic jungle tours—or stick to the golf course, if that’s your thing.
- La Jamaca is a smaller and more casual hotel that takes you off the beaten path and into a calm, island setting. Consider it a local-style hideaway where you can avoid the standard resort fare, if that’s your preference.
Culebra & Vieques (PR)
There are two islands off the coast of Puerto Rico that more intrepid travelers should know about: Culebra and Vieques. These are sometimes known as the Spanish Virgin Islands. They offer similar vibes of barely-populated, heaven-on-earth-style island living. Culebra is also home to one of the world’s most beautiful beaches: Tamarindo.
How can you get there?
You can take a ferry from the coastal town of Ceiba, which is the cheapest option to reach Vieques or Culebra. Others fly from San Juan, which is expensive but quick; both islands have their own airports.
If you prefer, you can also take a guided tour to/from the islands from San Juan, which includes plane tickets. I’d advise against doing a quick day trip; short day trips to islands usually put a huge strain on the environment and local community without giving much back. The best way to visit is to stay for a day or two.
Where should you stay?
- If you’re planning to stay a few days, I recommend staying at Ulala Culebra. You won’t be near the beach, but you’ll have near-panoramic views of the island and plenty of space to roam in your private suite.
- If you want a more exciting stay, book a room at Mamacitas Guest House. It’s right on the water and smack in the middle of the action, letting you walk to restaurants and nightlife. Just know that it’s got a hostel-style feel.
- If you want a stylish and unexpectedly cool stay in Vieques, book a room at Puertas. I’ve heard amazing things about this beachfront property, especially in terms of ambiance.
- Again, if you’re after style and something (pleasantly) surprising, stay at El Blok. It’s got character in just about every sense, from its dramatic, modern architecture to its jungle views.
Caribbean islands that don’t require a passport: US Virgin Islands
St. Thomas (USVI)
The United States Virgin Islands are home to three main islands—and each offers a distinct experience. The largest is St. Thomas, which is also the most developed. You can find large shopping malls, resorts from major chains, and just about any type of water adventure, especially in the main town of Charlotte Amalie.
How can you get there?
Fly into Cyril E. King Airport on St. Thomas. From there, you can head into Charlotte Amalie. Most visitors rent a car to get around the island, especially considering beach hopping is a popular activity.
Where should you stay?
- Stay at Hilltop Villas at Bluebeard’s Castle if you want to stay close to the action in Charlotte Amalie. From there, you can explore the island while staying close to popular restaurants and entertainment venues.
- If you’re looking for an all-inclusive experience, head to Margaritaville Vacation Club. Even if you’re not a Margaritaville type, you’ll enjoy this lovely beachfront resort—I promise.
St. Croix (USVI)
St. Croix is the most unique of the US Virgin Islands. It’s flatter than other islands and is also home to some of the best coral reefs in the region. Divers often head to the island, but snorkelers will have just as much to do.
How can you get there?
You can take a flight to Henry E. Rolhsen International Airport, which includes service from US cities like Fort Lauderdale and Miami. Others connect through San Juan in Puerto Rico. You can also take a ferry from Charlotte Amalie in St. Thomas. Just know that ferries can take up to two hours to reach St. Croix from St. Thomas.
Where should you stay?
- The Buccaneer is one of the most famous resorts in the Caribbean thanks to its long history. It’s kind of a cult favorite for families and couples that revisit St. Croix thanks to its unique country club atmosphere, massive property, and all-inclusive offers.
- Want total beach access? Book at Carambola Beach Resort. All you need to do is wake up, head to the beach or pool, veg out for a few hours, feed yourself, and then repeat the next day.
St. John (USVI)
As the smallest and least developed of the Caribbean islands that don’t require a passport, St. John is best for travelers who are independent and not afraid to get off the tourist track. In exchange for a little extra work (or spending more to stay at an ultra-lux resort), you’ll be treated to a more private, tropical escape.
How can you get there?
There’s no airport on St. John, meaning the only way you’ll arrive is via boat. You can fly into Cyril E. King Airport in Charlotte Amalie, then catch a ferry to St. John from Red Hook. The ferry only takes around 20 minutes.
Where should you stay?
- I mentioned ultra-lux in the introduction, which was a reference to The Westin St. John Resort Villas. Though very expensive, it’s one of the most highly rated resorts in the USVI, making it worth your money and the time it takes to reach.
- If you’re looking for a more boutique take on luxury, book a stay at Lovango Resort. It’s deliciously stylish, letting you drop off the map like a celebrity.
