How to Choose Your Caribbean Vacation: What Island Are You?

Fun fact: there are over 7,000 islands in the Caribbean. Well, to be more specific you have only about 2% of those to actually choose from. Perhaps we can steer your personality-type to a specific one. Are you a laid-back, (rum) cocktail-sipping lounger? Maybe you want to (attempt) making friends with a stingray. Or, you’re a romantic. Maybe all of the above. We won’t judge. And while we’re not going to detail all 7,000+ Caribbean islands, we will dilute the list down to the ones you’ll most likely be caught taking a selfie on. Here we go!

“The Beachie”

You’ve got a tan or want one really bad. Chances are, you’ve been working out and have been planning on flaunting what you’ve got once your toes hit the sandy shores. And let’s be honest, you probably don’t want to wear your vacation swim attire back home. Ever. Therefore, check out our post on the best Caribbean beaches or find your beach mecca on one of these islands:


Party time. You want to be able to say, “but why is the rum gone?” and already know you’re not going to feel that awesome come sunrise. But that’s okay, because on your trip, every day is “Sunday Funday.” Ready to dance the night away and wake up to a refreshing Painkiller? Then leave that tab open on one these party-oriented islands:

“White Linen and Romance”

You’re in love. You’re a man who never wears shorts, but you’re going on vacation with the woman of your dreams. Therefore you stock up on white-linen-everything before this trip and want to have a romantic (and comfortable) time. Ladies? You want to feel like you’re in a dream. Your wavy hair will be flowing in the Caribbean breeze and you want it to look good with the new chiffon attire you bought for this trip. Let us woo you with:

“Retirement is Calling”

You’ve got stories to tell. And a life well lived. Now, you’re wanting a quieter, more relaxing and reflective Caribbean vacation. You’d rather read a book, get a good night’s rest, eat some of the best food and relish every moment. Regardless of age, any young heart or old soul will find these islands to offer a slower paced vacation:

“Keep it Lean”

No, we’re not talking about your gym goals. You’ve got a budget and are in the get-it-all-in-in-the-shortest-or-cheapest-way-possible season of life. Scuba diving? Sure. (Is there a Groupon for that?) Snorkeling? Yes please. Cheap food? Always. Sleep? Meh. Majority of Millennials rejoice, here’s our recommends to keep your bank account happy:

Rest assured you will probably find something perfect for your stage of life in the Caribbean. Are you already a Caribbean island expert? We’d love to hear your personality type and what islands appealed (or appeal) to you!


Updated: December 7, 2015