The Unforgettables: What You Need to Pack for a Trip to the Caribbean

I don’t think I know anyone who hasn’t spent part of their work day daydreaming about a Caribbean holiday. Or someone who hasn’t plodded through the grey cold of the morning imagining aqua blue waters, white sand, a huge hot sun and an icy, creamy cocktail. It’s the greatest dream destination that is just as fulfilling in life.

You can literally pack everything you need for a Caribbean trip in a small backpack. The way I see it, you need something to wear on the beach, something to wear when exploring the hidden gems that each island has to offer, a beach towel, and a camera to document everything.

©Jade Anna Hughes

Amazing beaches exist all around the Montego Bay area in Jamaica. If you don’t mind stepping off the beaten track, or away from the resorts, you can befriend some of the locals who will be more than willing to show you their favorite spots. Just make sure to say that you aren’t on a cruise, as people tend to charge the cruise tourists extra for everything.

Bring your hungry belly to Kingston, Jamaica, because this is where you are going to taste some amazing Caribbean fare. While jerk chicken and rice and peas are classics, look out for the local Rastafarian places for incredible vegetarian food and some of the freshest juices you will ever taste.

A bathing suit is a given on the Turks and Caicos island of Providenciales, but comfy shoes are a must, too — there are beautiful views from the hills and stunning natural colors in Chalk Sound National Park. The island provides a perfect blend of nature, peace, food, and entertainment: hike in the morning, sunbathe in the afternoon, and dance in the evening.

©Jade Anna Hughes

You really can’t visit the Caribbean without checking out the amazing array of sea life swimming around in the turquoise waters. Scuba diving and snorkeling are fantastic in both Seven Mile Beach in the Cayman Islands and Saint Lucia’s Gros Islet. Exploring the barrier reef along Seven Mile Beach is one of the most fun, inspiring, and unique pastimes you can imagine. You do not need to pack any gear — you can find everything you need for a dive or a swim on the islands.

©Jade Anna Hughes

The great part of a Caribbean vacation is that while there is an off-season that comes with a little rain, the temperature remains around 80 degrees. In between rain showers it’s still perfect shorts and beach weather. You probably want to avoid hurricane season if you can, but if you don’t mind a little tropical rain, off-season is a great time to avoid the cruise crowds and join the locals in enjoying the real laid-back, friendly, and fun Caribbean lifestyle.

Bathing suit, towel, shoes, shorts, t-shirt, sweater, and camera, that’s all you need! And maybe a book for all that uninterrupted beach time you will be putting in. I suggest investing in a Holga-type camera and some film, too, as the beautiful island colors really translate well on film, leaving you with some whimsical printed memories of your trip.

This post is part of a series for Hipmunk Destination Unknown