The Caribbean is famous for luxury hotels and all-inclusive resorts. Millions of people visit the region each year though the vast majority come as part of a tour or as a cruise ship passenger. Traveling independently through the region can be difficult, with island hopping being very expensive, many of the islands offering only the very basic in public transportation, and the vast majority of hotels promoting all-inclusive packages. Here is where you will find walled-in, compound like beach resorts and small island towns better designed for short-term cruise ship visitors rather than travelers looking to stay and really experience the culture.

All that being said, exploring the Caribbean as an independent traveller can be a truly amazing experience, giving you a glimpse into the laid back lifestyles of this picturesque region of the world. Below are a few islands where independent travelers will have the easiest time exploring on their own.


In general, the people of the Caribbean are laid back, relaxed, and friendly. No where is this more true than on the island of Jamaica. Exploring the island will bring you right into the heart of rastafarian culture, give you a chance to see once-in-a-lifetime natural wonders, and give you a glimpse into a place that has captivated travelers for decades. Stop in at beachside bars for live reggae and fresh seafood. Grab a car and head inland, where you can hike through lush rainforests or swim in peaceful waterholes.

Traveling around Jamaica independently is very easy. You can opt to rent a car at the international airport though it might be easier to just arrange private transfers which can be quite affordable. In most towns you can grab a cheap cab to get around or arrange private tours with your hotel and/or local guides. In between the major cities and towns, there are even charter bus companies like Knutsford Express. Small local hotels come in all variations, from simple beachside bungalows to luxury hotels.


The Caribbean Island of Hispaniola is actually home to two different countries – Haiti and the Dominican Republic. When it comes to most independent travelers, the eastern two-thirds of the island, the Dominican Republic’s half, is where you want to head, though more off-the-beaten path travelers can also easily add a few days in Haiti.

Focusing on the Dominican Republic though, you’ll find that independent travel is quick and easy to plan out. Here is another island where renting a car is definitely something worth considering or you can just book travel with private bus companies which cover nearly the whole country. Independent hotels in the Dominican Republic are both plentiful and affordable, making even last minute travel planning an option. The best part of traveling to the country though has to be the vast diversity of activities you can find and book as an independent traveler – from ziplining through a jungle to horseback riding on the beach.

Puerto Rico

Part of the United States, Puerto Rico is a great option for travelers who want a bit of familiarity with a nice mix of Caribbean culture. Puerto Rico is filled with great resort hotels but equally has plenty of smaller, family fun places that cater specifically to independent tourists. Before you even start exploring the island, make sure you give yourself plenty of time to see the colonial capital of San Juan. With some of the oldest and best-preserved Spanish fortifications in the New World, plus gorgeous old colonial homes and churches, San Juan could easily be a trip in of itself.

If you want to explore beyond the capital, renting a car here is a very good option. There aren’t the same quality or number of private bus companies here and long-distances are more easily covered with the flexibility of your own rental car. With your car, you can also do quite a bit of independent exploring. Ask your hotel for some tips on what to check out nearby and you will often get recommendations for great secluded beaches, nice hiking trails, or great local restaurants.

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