Folks, Tax Day is upon us. REJOICE! It’s almost time to put your itemized deduction lists down, drop the W-2 forms, and step away from the IRS website. We can basically taste the finish line.

Whether you’re an accountant who hasn’t slept since the New Year or you’re just a plain old taxpayer, it’s pretty safe to say you could use a vacation after all that hard work. And, with the average Tax Day refund coming in at $3,120, you just might be ready to indulge in a proper getaway.

Not sure where your post-Tax Day celebration should go down? On the beach, obviously. More specifically, in the Caribbean! With its relaxed, slow-paced island culture, its clear blue waters, and its white, powdery beaches, we dare you to come up with a better place to unwind. The Caribbean is calling your name, my friend.

But, with so many awesome islands to choose from in the region, how do you figure out which one is best for you?

Never fear. We’re making it easy. Behold, five of the best Caribbean islands to spend your Tax Day celebration. You’re welcome.

1.) Jamaica



Aaaahh, Jamaica. You really can’t go wrong with this idyllic island nation. With pristine beaches, gorgeous coral reefs, mountain ranges, banana groves, and more, Jamaica has one of the most gorgeous landscapes of any island in the region. If it’s beauty you’re looking for, you’ll definitely find it here.

Beyond the beach, Jamaica has quite the rich cultural history, featuring incredible music and Afro-Caribbean creole cuisine. If you’re a Bob Marley fan, you already know the island is home to his signature Caribbean sound. But the awesomeness doesn’t stop with him—Jamaica is also known for its lively calypso and dancehall music scene. If you want to party the night away, this is the place to be.

Even better? There are a ton of cheap, quick flight options from the U.S., especially from the East Coast. Head to Jamaica, and you could be in island paradise faster than you can hang up on the IRS.

2.) The Dominican Republic



The DR is one of the Caribbean’s often overlooked gems. The island itself is geographically diverse in a way you won’t find anywhere else in the region—featuring bustling cities, sprawling rural countryside, idyllic coastal views, dramatic mountains, and gorgeous beaches.

When you’re not lounging under a palm tree or splashing in a lagoon, you can check out the colonial cities—the architecture in Santo Domingo or Puerto Plata can’t be beat—play dominoes with the locals, or dance the meringue on any street corner. Dominicans are famous for their parties, so rest assured that you can dance away your tax woes until the wee hours of the morning.

3.) British Virgin Islands



Looking to completely unplug for a few days? The British Virgin Islands—BVI for short—are where you should be. These are some of the least developed islands in the region, meaning fewer hotels, fewer tourists, and more untouched beach space. Perfection. What’s even better, the accommodations that do exist in BVI are super incredible. These islands are all about quality, not quantity.

That said, the air of exclusivity that BVI likes to cultivate means it can be a pricey vacation option. If you scored a sweet tax refund this year, go for it. But if you’re looking to save a few bucks, base your trip in a neighboring, more economical island—like Puerto Rico or the nearby U.S. Virgin Islands—and make BVI into a daytrip. You can island hop via local ferry systems, getting all of the fancy beach seclusion without any of the hefty hotel fees.

Now that’s what we call a tax haven.

4.) Puerto Rico

Sean Pavone/Shutterstock

Sean Pavone/Shutterstock

Speaking of Puerto Rico, it’s a pretty awesome spot to check out all on its own—whether or not you plan to make a daytrip over to BVI.

For starters, this island is the only one on the list that’s also a U.S. territory. That means, no passports required. You won’t have to worry about a lengthy customs process at the airport or about exchange rates and currency conversions—you’re technically still in the good ol’ U.S. of A.

Beyond the convenience of staying on American soil, Puerto Rico has something to offer travelers of all types. Looking to lay back and relax? Easy! Quiet beaches abound, and if you’re looking for some real seclusion, you can hop a ferry over to the off-the-beaten path islands of Vieques and Culebra.

Want to catch some waves? Puerto Rico’s got you covered there too, featuring incredible surfing beaches for the wave rider in all of us. If you’re looking for adventure, explore the island’s El Yunque jungle or check out the caves at the Parque de las Cavernas del Río Camuy. And if it’s a party you’re craving, the nightlife in capital city San Juan more than delivers. Adios!

5.) The Bahamas

BlueOrange Studio/Shutterstock

BlueOrange Studio/Shutterstock

Last but certainly not least, we’ve got the island chain of the Bahamas. This Caribbean nation has more than 700 unique islands and cays, meaning you really can’t go wrong when it comes to Bahamian beaches!

Hit Nassau on popular New Providence Island for a taste of luxury resorts, mega casinos, and pristine golf courses. If it’s ecotourism you seek, head northwest to Grand Bahama, where you’ll find breathtaking underwater limestone caves and botanical gardens. From either of these major islands, you can also take advantage of snorkeling, scuba diving, and fishing excursions—you can even swim with dolphins!

If you want to get off the beaten path, hop over to the Outer Islands. You’ll find fewer tourists, more untouched beach space, and a golden opportunity to drop off the grid entirely. Want to do something a little wacky? Go on a tour of the cays, each of which is uniquely weird—one cay is inhabited by a family of friendly, wild pigs, who will swim out to meet your boat in the water.

If doggy-paddling pigs don’t ease your Tax Day tension, I seriously don’t know what will.

So, how are you celebrating the end of tax season? Will you be hitting one of these islands in celebration? Let us know in the comments!


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About The Author

Hannah Winsten

Hannah Winsten is a freelance writer and marketing consultant living in New York City. A total travel junkie, Hannah came to CheapOair as a French translator and SEM associate after returning from a stint living abroad in Paris. She’s also working on her first book--you know you want to read it. Find her on Twitter at @HannahRWinsten.