Living in the Caribbean sounds like a dream come true, right?

Waking up every morning to bright sunshine, swimming in the crystal clear sea, eating fresh seafood and sipping cold beer with your toes in the sand. Life doesn’t get much better than that.

However, it’s important to note that it makes a difference where you live in the Caribbean. This is a large region and each island nation has its own unique culture and traditions. Depending on your location, your Caribbean living experience can vary quite a bit.

So, which is the best place to live in the Caribbean? The answer depends on your priorities. Let’s take a look at five of the most popular spots in the Caribbean and examine the pros and cons of living there.

The Bahamas


Technically the Bahamas are not part of the Caribbean - they are between the North Atlantic andthe eastern coast of Florida. However, they certainly have the laid back, rum punch vibe and the gorgeous sunshine of the other Caribbean islands on this list.

The vast majority of residents live in Nassau on New Providence Island, while many others have made their home in Freeport on Grand Bahama.


  • The people in the Bahamas are really warm and friendly. They will smile at you when you walk past and do their best to make you feel welcome.
  • There is a great expat community in the Bahamas, so it’ll be easy to make friends.
  • The beaches in the Bahamas are incredible - some of the best in the Caribbean.


  • The Bahamas can be one of the more expensive regions of the Caribbean. Make sure you have budgeted enough for groceries and other expenses. (You can save money by shopping at local markets.)
  • Eldercare services in the Bahamas can be very limited and there are no nursing homes, so keep this in mind if you are considering spending your golden years in the Bahamas.

Turks & Caicos


This sun-soaked British overseas territory includes 40 different islands and cays - yet only eight of them are inhabited. These remote string of cays are home to some of the most spectacular beaches and coral reefs in the world.

It’s known as one of the best spots in the region for diving and you’ll have your pick of quiet, unspoiled spots in the sand.


  • If you love diving, watersports and hanging out at the beach, this will be an incredible place to live. (Grace Bay Beach won TripAdvisor’s "Best Beach" award several years in a row and was featured in Conde Nast Traveller.)
  • This nation of islands is only a 2.5 hour flight from New York and 1 hour from Miami, so it’s convenient and easy to get to.
  • It's a stable, English-speaking country that uses the US dollar.


  • It's a pretty small island, which can leave you feeling a bit isolated.
  • Since almost everything but the coconuts needs to be shipped in, the food in the supermarkets can be expensive!
  • There really isn’t much to do here. (This is fine if the only item on your daily to-do list is to lie in a hammock and read a good book.)

Dominican Republic


The Dominican Republic is one of the most geographically diverse countries. It contains everything from beaches to deserts to stunning mountains and more. Beyond the capital, it’s mostly idyllic and rural, filled with lush jungles and waterfalls.

If you plan to stay here for a while - try your best to learn some Spanish. It will allow you to communicate and connect with the locals on a deeper level, which will enhance your experience.


  • The cost of living here is generally much cheaper than it would be in the USA. (This is especially true if you avoid the tourist traps.)
  • The Dominican Republic has recently made major upgrades to the airports, allowing for easy travel in and out of the country. They have improved the roads, which has brought down the cost of importing goods.


  • Things move slowly here, so if you’re used to a fast pace of life you might find that frustrating.
  • You'll have to lower your standards for things like transportation, efficiency, etc. Life can still be a bit chaotic and you’ll have to roll with it!

Cayman Islands


The Cayman Islands have been depicted on the silver screen as glamorous Caribbean hideaways where jet-setters hide their millions. In real life, it’s a much more fascinating and complex place to live. It’s a very cosmopolitan place and more than half the population is from somewhere else - yet it still has a very rich local culture.

It's very similar to the USA - when it comes to grocery stores, restaurants and big box outlets. Whether this is a pro or a con depends on whether you want to live somewhere completely different or have the comforts of home.


  • The economy and infrastructure is strong and stable, especially compared to other Caribbean locations.
  • There's so much to do here, with lots going on in Cayman Brac, Bodden Town and the Sister Islands, plus plenty of hiking, caving and shipwreck diving.


  • Traffic in the Cayman Islands can be frustrating and the public transport system isn’t very reliable. You’ll need to learn which times of the day to avoid driving.
  • The heat is pretty intense! It’s a tropical climate and is sweltering and humid all year round. 

Puerto Rico


A blend of Spanish and American influences, Puerto Rico is a vibrant and unique place to live. It’s rich with history, the food is delicious (try the suckling pig) and the beaches are spectacular.

Many of the conveniences of the USA can be found here, such as Costo and Walmart. (Again, depending on your lifestyle this may or may not be desirable.)


  • If you love art and history there are many museums here to enjoy, covering everything from European painting to revolution.
  • There are lots of events, parties and festivals here - so you’ll have a busy social life.
  • The money is the same as the USA, which makes things a lot easier.


  • In the high season, Puerto Rico can get busy with tourists.
  • It's hard to live here if you are a vegetarian, as pork is used in almost every dish!
  • Getting things done can often be inefficient. Don't be in a rush and be prepared to spend a lot of time waiting at the supermarket, bank, doctor's office, etc.

Considering a home in the Caribbean?

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