Which Caribbean Island Should I Choose?

by  Melissa Kravitz Hoeffner | Feb 23, 2022
Aruba / iStock / nisangha

Traveling to the Caribbean is always a good idea. The glossy blue waters, the breezy palm trees, the laid-back vibes, and friendly Island culture. Other than leaving to go back home, the hardest part of a Caribbean vacation can be planning which island to visit. With over 7,000 islands dispersed between 13 countries and seemingly endless resorts, rentals, and experiences available on each island, how do you choose which Caribbean Island is right for you? Spoiler: There’s no wrong choice, you really can’t go wrong in the Caribbean. Still, we’ve made this guide to the islands to help you with figuring out all of the below: 

– What’s the best time to visit the Caribbean Islands?

– Which Caribbean Island should you choose?

– Where to stay in the Caribbean Islands

– What to do in the Caribbean Islands 

What’s the best time to visit the Caribbean Islands?

The Caribbean Islands are beautiful year-round, but many tourists choose to avoid hurricane season, which runs from early June through November. Typically, the fall is the cheapest time to visit the Caribbean islands, as school is back in session, and most North American and European travelers have already gotten in their beach time over the recent summer months. Caribbean high season is December through early January, and then again during spring break, which is typically in April. 

Which Caribbean Island should you choose?

While the Caribbean can be a one-size-fits-all situation, that is, you can’t go wrong with pristine beaches, aquamarine waters, and island hospitality. Depending on budget, timing, and the goals of your trip, one island may fit your Caribbean itinerary better than others. Whether you’re a honeymooner or an avid solo traveler, we have the best Caribbean island for your specific trip curated for you! 

The Best Caribbean Island for Luxury Travelers: Turks & Caicos

The ultimate Caribbean destination for upscale relaxation, Turks & Caicos is a dreamy island with direct flights from major cities like Atlanta, Miami, Charlotte, Boston, New York City, Chicago, and Philadelphia, so you can optimize your vacation time for a long weekend or extended getaway. Known for stunning white sand beaches – almost pink in contrast with the sparkling blue waters – Turks & Caicos is known for having sunny skies at least 360 days a year, plus hosting many celebrity vacation homes and a range of premium accommodations, including five-star resorts and beachfront villas. Prices to stay and dine in Turks & Caicos tend to be higher than other Caribbean Islands, but you’re getting a less crowded, more luxe experience, plus you can use your U.S. currency. 

The Best Caribbean Island for Budget Travelers: Dominican Republic 

The hoards of resorts and hotels in The Dominican make for steep competition, and with Caribbean competitors come deals! This Spanish-speaking oasis has seven international airports, so depending on your origin, you can find a flight within budget. From there, fantastic deals abound, like all-inclusive packages at respected international vacation chains, plus plenty of vacation rentals and hostels at under $30 per night. The food is excellent in The Dominican, with plentiful culinary options that won’t break the bank. 

The Best Caribbean Island for Solo Travelers: Jamaica

Stella got her groove back here, and you can, too. Whether you’re looking for love or just a good time with a paperback at a Blue Stripe, Jamaica is the Caribbean island for the ultimate you time. The birthplace of reggae, Jamaica is as laidback as it is alluring, so you can unwind with the unofficial national motto of “no worries.” Make like Marilyn Monroe and Meghan Markle and check into the Jamaica Inn, a family-run beachfront resort in Ocho Rios or stay low key and reserve a room at the boutique S Hotel Jamaica.

The Best Caribbean Island for Family Travelers: The Bahamas

Booking a stay at Atlantis Paradise Island is a quick route to an unforgettable family trip for kids of all ages. With several accommodations, activities, and entertainment options, this paradise built on a beachside oasis offers plenty on the itinerary without planning much more than flights. A group shot in front of the Bahamas’ idyllic turquoise waters will also bring a certain optimism to your everyday life when it’s framed back at home. The Bahamas is also well-known for its swimming pigs, which are worth a day trip to go see. 

The Best Caribbean Island for Group Trips: Aruba 

Known for its range of all-inclusive properties, Aruba is a beautiful Caribbean Island for bachelor and bachelorette trips, friends and family reunions, or other group meet-ups that require sunshine, swimming, and easy-to-split tabs. Known as “One Happy Island,”  this white sandy oasis in the Dutch West Indies is guaranteed to improve your mood long after you pack your bags to (sadly) depart.  

The Best Caribbean Island for Honeymooners: Anguilla 

A British territory on the east edge of the Caribbean, Anguilla is more remote than some more populated Caribbean Islands, with a more private and luxurious vibe. Four Seasons Resort and Residences Anguilla is the ultimate property to be pampered as newlyweds, with high-end accommodations and activities – like a sunset sail– plus opportunities to enjoy the flavors of the culinary capital of the Caribbean. 

What to do in the Caribbean Islands 

While each individual Caribbean island offers its own unique local culture and charm, the activities offered in the region are quite similar. Book a day trip to go deep-sea fishing, snorkeling, or scuba diving. Go on a waterfall hike or ask your hotel’s concierge or rental host for little-known natural gems in the area. 

Want to take that trip for free — and score some valuable miles for your next excursion? Check out our top pick travel credit cards for the best welcome bonuses, perks, and plenty of cash back.

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