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How to Choose Which Caribbean Island to Visit on Your Next Vacation

How to Choose Between Caribbean Islands

Planning a trip to the Caribbean? If you find yourself daydreaming of clear waters, swaying palm trees, abundant sunshine, and plenty of rum — you’re on the right track.

You know the Caribbean is beautiful and you’re confident that it’s the perfect part of the world for your next vacation. But when it comes down to choosing where in the Caribbean you want to go, how do you decide where exactly you want to visit?

For those who are unfamiliar with this entire region, picking an island and planning an entire vacation there can seem daunting. What will it be like? Where will you get the most bang for your buck? Are there certain islands to avoid or specific areas you want to be sure not to miss? Where’s the best spot to honeymoon after months of wedding planning — or which island should you head to if you’re looking to do a solo adventure trip?

In this article, we’ll help you out. Sure, the Caribbean covers an expansive area, from the southeast area of the Gulf of Mexico all the way over to the northeast corner of South America. In fact, over 7,000 individual islands make up what is known as the Caribbean.

But that doesn’t mean that planning a trip there has to be overwhelming. In fact, you can even take a quiz to figure out which Caribbean island is the best fit for your personality! If you need help figuring out how to navigate the Caribbean waters — literally — we can help.

Choosing the Right Caribbean Island

Like all trips, when it comes to Caribbean islands, most of the decision will come down to what kind of trip you’re looking for and how much time you want to spend planning. For example, are you looking for a party island or a secluded getaway? Do you want to pore over the details or pay one flat fee and then not have to think about it again?

Going the all-inclusive route is a great option if your main objective is to book it and be done with it. But if you want the best possible deal, or more flexibility, then planning the trip step by step may be your best bet.

Let’s take a look at some of the most popular hot spots in the Caribbean to decide which might be the best fit for you.

The Bahamas

The Bahamas

For a tropical getaway that’s just a short flight off the east coast of Florida — and for a chain of islands that has it all — the Bahamas is a great option. The second you step off the plane, you’ll be greeted by an unmistakable air of island time.

Within the Bahamas, you have tons of options depending on what island vibe you’re going for — and it’s pretty easy to hop between your favorite options. Nassau is a classic tourist destination — and home to the world famous Atlantis on Paradise Island — while places like Hope Town in the Abacos or Harbour Island on the island of Eleuthera offer a bit more of an undiscovered feel.

Turks & Caicos

Turks & Caicos

Turks & Caicos is a bit more pricey than other islands, but you won’t find water clearer anywhere else in the world. If you’re looking to spend your Caribbean vacation in the lap of luxury, Turks & Caicos is a great option for you.

Home to some of the most pristine beaches known to man, Turks & Caicos is also famous for fresh conch and abundant rum. If you’re looking to kick back, wind down, and enjoy the simple pleasures of life — but punctuate all that with adventures like sea kayaking and fishing — then Turks & Caicos is your dream destination.

Puerto Rico

Puerto Rico

Want to plan a trip with the least amount of hassle involved? Puerto Rico might be a great option for you. Since it’s a U.S. territory, you don’t even need a passport to get to Puerto Rico. This also makes it a great option if you find yourself planning a last minute trip and don’t have much time for figuring out trip logistics.

Another draw of Puerto Rico is that this island seems to have it all — rich history, lively culture, rainforests, jungles, beaches, surfing, diving… and a whole lot of charm! Don’t miss a walk through the streets of Old San Juan if you want a healthy dose of colorful houses and vibrant locals.

Puerto Rico is also affordable, easy to get to, and has a lot to offer all on one island.

St. Lucia

St. Lucia

St. Lucia is another one of those spots that offers breathtaking natural scenery — but with a hefty price tag. It’s a popular honeymoon spot, which over time has hiked the prices in St. Lucia way up. If you head here, opt for a luxury resort but plan to pay lots of extra fees, like cab rides down the mountain from Ladera or add ons for excursions like parasailing, wind surfing, or volcanic baths.

Still, St. Lucia has earned every bit of its popularity. Deep waters just offshore give the ocean an inky blue tint, while the lush green Pitons jut up off the southwestern coast, giving St. Lucia a dramatically beautiful backdrop for all of your island relaxing needs.

The Virgin Islands

British Virgin Islands

Looking for a trip that packs an adventurous punch? The British Virgin Islands are a favorite for sailing, snorkeling, and even deep sea fishing charters. Plus, the BVIs boast the kind of scenic beauty that make them picturesque enough to be your computer screen saver.

The BVIs make for an exclusive an upscale getaway. You can find sailing, seclusion, world class restaurants, and isolated coves that beckon you to slow down, take a breath, and enjoy the best life has to offer. You can find resorts and hideaways, rocky outcroppings and expansive beaches, yachts and fishing boats all in this one little country.

Take a Cruise

Sure, booking a cruise may be the most touristy way to see the Caribbean. But if you want to get a good overview of the general region without having to figure out the logistics of island hopping, a cruise may be the perfect fit for you.

A cruise will let you see multiple Caribbean islands, all in one trip. It takes a lot of the hassle out of planning, budgeting, and figuring out logistics — once you’re booked, most of that is taken care of for you. All you’ll have to do is pick which excursions you want to fit into your agenda.

Most cruise ships in the Caribbean — depending which islands you hit on the ship, of course — offer activities like island tours, snorkeling, sailing, shopping, and more.

If these sorts of activities appeal to you and you don’t mind being herded around with a large group of tourists, taking a cruise might be a great way to see a good swatch of the Caribbean and get a couple more stamps in your passport, all in one trip.

Other Tips for Traveling to the Caribbean

There’s more to trip planning than just choosing an island. In this section, we’ll explain a few other things you need to know before you go.

Flights, Weather, and Other Factors: Some things you’ll want to consider as you plan include your budget, of course, but also the cost of living on the island, weather patterns and seasons, activities, and ease of access.

When it comes to flights, you’ll want to take a look at what’s available and how difficult the island will be to get to. How many flights head there each day? Usually, the more flights per day, the cheaper these flights are — and the more flexible the schedule will be for you.

However, the flip side is that more flights per day usually means more tourists, too. Not everyone is willing to book a multi-leg process to get to the island of their choice, so if the journey there is fraught with planes, boats, and cars, you’ve likely found yourself a hidden gem.

Also, though the Caribbean label applies to thousands of islands, they’re not all located in the same kinds of climates. One island may get torrential downpours every April while another is sunny and dry. Of course, you’ll also want to look at the hurricane season and annual averages when you consider what time of year you want to take your vacation.

Passport: If you don’t have a passport already, make sure to get that now! You’ll have to pay extra to expedite it if you wait too long. Also check to see when your passport expires — in some countries, there are rules about not traveling within 6 months of the expiration date.

Global Entry: Want to skip security lines and secure a hassle-free re-entry into the U.S. upon your return from the islands? Look into Global Entry. It will save you a ton of time — both when you get to the airport and when you’re trying to make it back home to your own bed!

Whether your main objective is to add as many stamps as you can to your passport — or just to find yourself on a beach with a fruity cocktail in hand as soon as possible — the Caribbean has something for you.


Author’s Bio

Skye Sherman is a freelance travel writer based in South Florida. Her work has appeared in numerous publications, including Palm Beach Illustrated, Skyscanner, InJupiter, and more. When she’s not exploring a new locale or penning a travel story, you can find her engrossed in a good book (sometimes all three at the same time). For more travel inspiration and South Florida living, follow Skye on Instagram @skyesherman.