How to Choose the Right Caribbean Island for Your Vacation

How to Choose the Right Caribbean Island for Your Vacation

Before you choose a Caribbean island for your next vacation, think about the kind of getaway you’d like to plan and use these must-read tips!

The Caribbean is an amazing place to visit, partially because there are so many different islands and so many different cultures in such a relatively small area! If you want to relax, there are white and pink sand beaches; there are hundreds of miles of reef to explore if you’re looking to scuba; there are old forts and plantations for the history lovers.

With so many affordable options in the Caribbean, it’s a perfect destination for any type of traveler!

How to Choose Which Caribbean Island to Visit


How to Choose the Right Caribbean Island for Your Vacation


Couples Getaways

If you’re interested in an island couples’ getaway, Puerto Rico might just be the perfect romantic destination for you. This island’s lush natural beauty and old Spanish charm make it a top honeymoon destination for many Caribbean-bound couples.

During the day, enjoy lounging on the beach with a glass of Bacardi rum from the distillery in Cataño, or take a walk down the shaded Paseo de la Princessa. At night, salsa dance in the cafés of Old San Juan or take a sunset cruise, complete with champagne.

The gorgeous Fortaleza Suites Old San Juan is in the heart of Old San Juan and is close to some of the trendiest restaurants and shops in the area!

How to Choose the Right Caribbean Island for Your Vacation


Family Travel

St. Maarten can be a great and affordable family vacation in the Caribbean, offering fun activities for kids of any age. Orient Beach’s Butterfly Farm is home to thousands of brightly colored butterflies, and nearby the family-friendly Le Galion beach. Downtown Simpson Bay not only offers gelato and duty-free shopping, but a famous carousel!

The Sonesta Maho Beach All Inclusive Resort, an Ascend Hotel Collection® member, is right on Maho Beach and within a short distance to all of the highlights above, where kids can watch the planes land and take off (and parents can grab a drink at the swim-up bar).

How to Choose the Right Caribbean Island for Your Vacation


Solo Travel

Anyone who’s read our previous articles on Caribbean travel knows how we feel about Bonaire; it’s a great, safe, and welcoming place to visit for solo travelers. The island culture is friendly and laid back, the island itself home to great natural reefs to explore.

The perfect place to learn how to scuba! It’s less touristy than many of the more well-known Caribbean islands, making it perfect for travelers who want to enjoy the slower pace of sun, surf, sand, and good company.


Water Sports

The Cayman Islands are home to some of the most amazing dive sites in the Caribbean, ranging from natural reefs to sunken ships from every age.

Grand Cayman is also home to “Stingray City,” a collection of sandbars off the North coast which offers adventurous swimmers the chance to swim with, pet, and even feed the rays! Local charter companies offer ski and boat rental, and some hotels like the Comfort Suites® Seven Mile Beach will even help you book fishing, kayaking, or dolphin-sighting tours.

How to Choose the Right Caribbean Island for Your Vacation



Sometimes, a getaway needs to be a chance to get away and relax; Curacao’s wonderful adventure opportunities offer travelers plenty of chances to rest and rediscover themselves. In fact, the island’s name comes from “Isla de Curacion,” or Island of Healing, and many of the island’s resorts boast phenomenal restorative spas.

The Blue Bay Beach Villas gets excellent reviews, offers an outdoor pool, a fitness center, and a private beach area.

How to Choose the Right Caribbean Island for Your Vacation


The Island Hopper

Looking to visit multiple Caribbean islands in one trip? The Bahamas are the perfect destination.

It’s very easy to book an island-hopping tour to visit all of the main islands of the Bahamas, and their proximity to both the Florida Keys, Cuba, and Haiti and the Dominican Republic make it possible to take a boat or pond hopper to the greater Caribbean area. Still, with over ten unique islands to explore, leaving the Bahamas themselves is hardly necessary!



Looking to party? Aruba is among the best party islands in the world! With great clubs like the Zombie Room, Club Hipsz, and the infamous Senor Frogs, there will always be somewhere to find a drink and a dance floor. If you’re not as confident in your skills, you can brush up at Aruba Salsa, and then take the Kukoo Kunuku party bus for dinner, an island tour, and a non-stop party!

So whether you are looking for a romantic getaway, a solo journey, or a vacation with the whole family, it’s easy to choose the perfect Caribbean island!



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  1. Hi! Looking for a great honeymoon spot! Looking for beautifu beaches, relax , hiking and nightlife like dancing. Please let me know excited:)

  2. Jennifer Murray Schmitt says:

    I am taking my daughter on a trip for her 20th birthday, I must admit its partly selfish on my part I need a vacation badly. Anyhow, my husband is worried about our safety and I understand. Things we want to do, horse back riding, we are both experienced. Swim with turtles and rays, snorkeling and of course one night to go to a club and dance and drink. What island do you recommend for all that?

  3. This is indeed a great post with lots of ideas for a vacation! I’ve been to the Carribean before and I know how amazing they can be. There is a bit for everyone there…