By Eben Diskin | Published on July 31, 2024

 
When you're planning your dream Caribbean vacation, start by asking yourself a few questions. First, "What is the best Caribbean island to vacation on?" And then narrow that down further with "Am I a thrill-seeker or a chill- seeker?". Luckily, each Caribbean island is unique in its ability to satisfy every traveler. Pick your travel style by selecting a team and start the Where Should I Go in the Caribbean? quiz to find the best places to vacation.

Team Thrill Or Team Chill

If you're asking yourself "Where should I go in the Caribbean?" you need to start by identifying your travel style. Are you dreaming of days spent soaking up the sun on a sugar-sand beach, or are you looking for heart-pounding thrills like an epic dive into Cozumel's coral reefs?

Based on your answers, you'll learn whether you're a thrill-seeker or a chill-seeker, and what islands are calling your name.

Take the quiz
01

What is your idea of
a perfect caribbean vacation?

  • Lounging by the pool with a drink in hand
  • Flying 100 feet over jungle terrain on a zip line
  • Exploring an island's rich history
  • Indulging in the local cuisine
02

What is your ideal way to
spend an island afternoon?

  • Chilled out on a postcard-worthy beach
  • Snorkeling among coral reefs
  • Shopping for unique souvenirs
  • Eating and drinking at local restaurants
03

On vacation you're
Likely eating...

  • Burgers and fries — just like home
  • The local delicacy — I'm always up for something new
  • Whatever's quick because I have sights to see
  • As much seafood as I can
04

What's your favorite
part of being on vacation?

  • Decompressing from the stress of my everyday routine
  • Adrenaline-pumping activities I can't do at home
  • Experiencing a different culture
  • Discovering new foods and local flavors
05

If one setting describes your
personality, what would it be?

  • The beach because I'm cool, calm and collected
  • A waterpark because I'm the life of the party
  • A museum because I'm an old soul
  • A swim-up margarita bar because I like to take things easy
06

Who are you
traveling with?

  • My significant other
  • My travel buddies
  • My family, kids included
  • A bachelor or bachelorette party
07

What is your idea of the
perfect night in the caribbean?

  • Enjoying a glass of wine with a sunset view
  • An all-night pool party at the cruise ship's private island
  • Taking a local brewery tour
  • Bar-hopping around the city
08

What vacation activity
gets you the most excited?

  • Catching the sunset or sunrise over the ocean
  • Going scuba diving
  • Spotting unique wildlife
  • Sampling all of the delicious street food

If you chose mostly a's, go to:

Perfect day at Cococay

Bahamas

You're looking to chill on your Caribbean vacation, to get away from the stresses of everyday life, sit by the pool, and let your troubles wash away. Perfect Day at CocoCay takes care of everything for you. From beach chairs and umbrellas to over-water cabanas and an infinity pool, you're sure to reach maximum chill mode. You won't have to go far for drinks, either, as a 33,000 square-foot pool with a swim-up bar is just steps away. And if you need to let out a little energy, Thrill Waterpark has you covered.


If you chose mostly b's, go to:

Cozumel

Mexico

You're a thrill-seeker. Your ideal vacation is hitting the water and exploring everything this region has to offer in the most exciting way. Dive beneath the waves in Cozumel for world-class scuba diving through the second largest reef system in the world. Then, hop on a boat for a whale shark excursion. Catching a peek of these big and beautiful fish is an exhilarating experience.


If you chose mostly c's, go to:

St. Thomas

You're a chill-seeker looking for a vacation focused on exploring a destination's culture and history at your own leisure. Dive right into the history of St. Thomas with a visit to one of the island's most famous landmarks, the 99 steps. Built in the 1700s, these steps pass through nearly all the hills rising from the harbor of Charlotte Amalie. With colorful flowers on each side, you'll get some beautiful photos as well as a comprehensive walking tour through town. When you're ready for some shade, spend a laid-back afternoon immersed in the Pirates Treasure Museum. The museum contains actual artifacts from the wild seafaring days of the notorious Blackbeard. Then, grab a drink and a hammock on the beach for maximum chill time.


If you chose mostly d's, go to:

San Juan

Puerto Rico

You're a thrill-seeker, but your brand of thrill looks like swim-up margarita bars, pool parties, and nightclubs. San Juan, Puerto Rico is one of the best places to vacation to do just that. San Juan is filled with bars, nightclubs, cabaret shows and casinos. And for a feel of the local rhythm, take a salsa or merengue dancing class. Rum is cheap here, too, since Bacardi calls the island home so drink your fill of expertly made cocktails. Foodies will also find plenty of reasons to get excited about Puerto Rico — there's nothing more comforting than mofongo and bite-sized empanadillas.



T

here are two types of vacationers: those looking for adrenaline-pumping thrills, and those looking to take it easy and chill. Maybe you fall somewhere in between the two. These dramatically different mindsets go a long way toward shaping what your vacation looks like, and it's important to understand how they align with your goals when choosing a destination in the first place.

Thrill-seekers may plan their travels around activities like ziplining, sea kayaking, ATV'ing, skydiving or scuba diving, while chill-seekers are looking to leave behind the daily grind and take full advantage of island time.

Epic Vacations for Team Thrill

Sure, the Caribbean typically conjures visions of relaxing on the beach, but that's only part of the experience. If thrills are what you're looking for and you find yourself wondering, "Where should I go in the Caribbean?" and "What is the best Caribbean island to visit?" you're in luck. Many Caribbean islands are full of adventure just waiting to be discovered.

Explore Cozumel's Colorful Reefs

An island off the coast of Mexico's Yucatan Peninsula, Cozumel is the perfect Caribbean vacation destination for thrill-seekers. Sure, you'll find beautiful beaches here, but you'll also be able to dive into some pretty exciting activities as well. Cozumel's Santa Rosa Wall is the site of some of the Caribbean's best scuba diving, with an abundance of grouper fish and one of the largest reef systems in the world. Snorkeling is also an option, with both half- and full-day excursions available. If you like to fish, you'll also find plenty of reasons to enjoy Cozumel. The island's clear waters are famous for their sailfish, mackerel, mahimahi, kingfish and barracuda, and whether you're a veteran or a newbie, tours are available to guide you through your deep-sea experience.

Kayak Alongside Jamaica's Waterfalls

Jamaica may be known for its chill reggae vibes, but the island has much to offer in the adrenaline department as well. Kayaking and rafting will get your blood pumping, especially on the Martha Brae River near Falmouth. You can also check out a River Rapids Adventure in Ocho Rios — an area known for its beautiful waterfalls — or explore independently in a kayak or inner tube. If you'd rather get in the water than simply float on it, go snorkeling along the vibrant coral reef at Doctor's Cave Beach in Montego Bay, or get up close and personal with nurse sharks in Ocho Rios.

Ride the Waves at CocoCay's Thrill Waterpark

The thrills don't get much more intense than Perfect Day at CocoCay, Royal Caribbean's private destination in the Bahamas. Great for both thrill- and chill-seekers, Thrill Waterpark here certainly lives up to its name. With 13 waterslides, a wave pool and an adventure pool, there's no shortage of adrenaline-pumping water experiences. If you're still looking for more, check out the 1,600-foot zip line high above Harbor Beach, or soar even higher in a hot air balloon.

Relaxing Vacations for Team Chill

The Caribbean is almost synonymous with relaxation. If you're seeking the best places to vacation as Team Chill, you're content to simply lay back and let the island breeze (and crystal-clear waters) wash over you. And why not? You've earned it. The sun may be hot, but in the Caribbean, chill is a way of life.

Kick Back at the CocoCay Beach Club

A destination exclusive to Royal Caribbean guests, Perfect Day at CocoCay is designed to have something for everyone. In addition to the waterpark, zip line and other high-octane activities, you'll find plenty of ways to simply chill and enjoy the sunshine. The Coco Beach Club, for example, is full of beach chairs and umbrellas, and it even has an infinity pool, clubhouse and upscale restaurant. You can also rent overwater cabanas. For a more relaxing water experience than Thrill Waterpark, head to Oasis Lagoon, the largest freshwater pool in the Bahamas. This 33,000 square-foot pool is ideal for cooling off by a swim-up bar and splashing around with the whole family.

Stroll Through History in Tulum

Chilling doesn't always have to mean sitting on a beach. A chill vacation can also carry immense cultural and historical benefits, especially when it comes to destinations in Mexico with a rich indigenous history. Tulum, for example, has an abundance of Mayan ruins, with some sites dating back to 300 A.D. Protected by a limestone wall, the old city includes a field of rolling hills and black and gray stone ruins. The most impressive are the Castillo — a castle sitting on the edge of a limestone cliff over the sea — and the Temple of the Frescoes, which has a mural painted on the interior.

Explore St. Thomas' Pirate Past

St. Thomas is the perfect mix of history, food and scenery that'll make you wish you had at least a week to soak it all in. The city of Charlotte Amalie is famous as a one-time haven for pirates, particularly Blackbeard. You can visit Blackbeard's Castle, built in 1679, as well as the largest collection of life-sized pirate statues in the world. When you're ready to tuck into some local cuisine, you'll find the island's special take on West Indian food like callaloo and Johnnycakes, as well as chocolate-dipped coconut patties. You can also try St. John Brewers Virgin Islands beer here if you're craving a taste of island ale. When you're ready to work off those coconut patties, hike up to Government Hill for panoramic views of the sea and look out on the docked ships.

 

Written By
EBEN DISKIN

Eben Diskin is a travel writer, amateur pizza connoisseur, avid Indoorsman, and the Senior Staff Writer at Matador Network. While traveling, he pretends to enjoy activities like hiking, camping, fine dining, and museums, when all he really wants to do is drink Jack and Cokes at the hotel bar. He has a degree in History from Wheaton College and a definitely-not-useless Master's in Fiction Writing from the University of Edinburgh. 

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