The Best Caribbean Islands for US Travelers

Try to list the Caribbean countries and you realise the region isn’t just big – it’s almost overwhelming. Cuba and Haiti are incredible destinations in their own right, while Jamaica, Bermuda and Barbados conjure up images of a palm-strewn paradise – and the reality isn’t too different.

A number of US citizens have retired to the Caribbean, turning vacation experiences into a permanent way of life, and there are some obvious benefits to making a home here. For others, the practicalities of taking a short vacation somewhere so close, yet so different, to the US is part of the attraction. Now the rules have been relaxed and some travel to the Caribbean is once again permitted, let’s see what all the fuss is about and explore the destinations you should think of visiting first.

Please review the official CDC travel advice prior to any travel.

Grenada is formed of the main island (also called Grenada), Carriacou and Petite Martinique, and is part of a larger group known as the Grenadines. It’s the variety of things to do and places to stay here that really pull in the visitors, with hotels to suit every budget readily available. There are dozens of beaches, waterfalls and festivals on the main island, with the unmistakable smell of nutmeg – the primary export of Grenada – never too far away. It’s a great option if you want to avoid crowds and soak up a little nature in the Caribbean.

From romantic resorts to luxury hotels, it’s easy to see why Barbados is one of the most popular honeymoon destinations in the world. The charm offensive begins as soon as you step off the plane, as the warm air and cool breeze combine to give you an unforgettable welcome to the island. It’s not all pampered excess here, however, with local experiences and self-contained stays also available for those who like to remain semi-active while away. Make sure you experience some culture outside of your hotel, as there is plenty to see on the island.

This British overseas territory is formed of the main island and several smaller isles and keys. The name Anguilla is derived from the Italian for eel, a nod to the shape of the islands. Its long, thin construction can make it hard to navigate, but once you get used to it – and found a convenient villa or hotel in which to stay – there’s plenty to explore. Best of all, African, French, British, Caribbean and Spanish influences combine to create some of the best cuisine you’ll ever try. The islands are also notable for their fantastic coral reefs just waiting to be discovered by eager divers.

Known as Waladli or Wadadli by the local population, Antigua is also part of the Lesser Antilles, like our previous pick Anguilla. Capital city Saint John’s is in the northwest of the island, and is one of the largest settlements in the area. Antigua and neighboring Barbuda form a close partnership and operate together as a collective administration. The main airport serves the US mainland, with regular flights available from several airlines. There is also a domestic route to Barbuda, and for many this is seen as an affordable luxury destination, with plenty of high-end hotels in which to set up camp.

Larger than most Caribbean islands, both in terms of population and land mass, the Bahamas is reliant on tourism to drive its economy – with everything from budget-friendly hotels to luxe lodgings available. It was a favorite stop on many Caribbean cruise routes before Covid-19 put a halt to US ships docking at the major ports; expect a rapid return to this form of travel here in the next few months.

To get a sense of the cuisine on offer here, you only need to look at the most popular local events; who could resist the annual Pineapple Fest, or the equally delicious Crab Fest? Ecotourism is also set to be a big part of what the island offers soon. If you do visit, attend some of the sporting events that take place here to see some of the best athletes in the world perform in their own backyard.

An overseas territory of France, the six inhabited islands that make up Guadeloupe feel like an entirely different part of the Caribbean. European travelers have it easy here, as they can spend their euros and even hop on their usual continental mobile networks as soon as they arrive, but things aren’t too bad for US travelers, either. The local food and drink are particularly appealing for anyone looking to try something unique, and visitors can relax in their hotel knowing that this is one of the safest islands in the Caribbean, with a low crime rate.

Jamaica is such an obvious choice that we toyed with the idea of not even including it here, as it will already be on many people’s travel wish lists. How about booking a hotel in the bustling capital Kingston, which is a frenzy of activity from morning to night, or a more chilled retreat in Montego Bay on the opposite side of the island? There are so many things to do in between that it’s impossible to pick just one. The rich cultural heritage from film and music alone gives a great idea of what to expect here. Just treat the trip as an adventure and you’ll have the vacation of a lifetime.