12 Worst Travel Mistakes You Can Make in the Caribbean

Avoiding these errors will help you enjoy time in the iconic region instead of letting things go south.

Paradise Island
Updated May 28, 2024
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If you plan to step up your travel game this year, a visit to the Caribbean will enchant you with what it has to offer. 

This famous region is the stuff of tropical dreams, with turquoise sea views, lush greenery, and endless fruity drinks seemingly in every corner.

Before you jaunt off to paradise, however, make sure you have all your ducks in a row. Here are some bad mistakes you'll want to avoid making on your Caribbean vacation.

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Only considering a cruise

Jag_cz/Adobe luxury cruise boat with tropical Seychelles island

We aren't hating on cruises, but if that’s the only way you’ve ever explored the Caribbean, you might not realize that you have other options.

Skipping a cruise is especially good advice if you want to avoid congested tourist bars and souvenir shops designed with mass appeal in mind or if you're just looking to keep more money in your wallet.

The better way to get to this iconic destination arguably is via plane, as there are ample flights to a wide variety of destinations. And if you get to take a seaplane, that counts as a true adventure.

Forgetting to bring cash

Taras_Muroslavovuch/Adobe male shows empty pockets

Many Americans simply don’t bother to have cash on hand. But when heading to the Caribbean, be sure to bring some money with you and secure it smartly.

Without access to cash, you might miss out on quirky side-of-the-road vendors, which aren’t exactly set up for plastic. You also need to be prepared to tip if you want the best service.

Many islands accept U.S. dollars, too, which is convenient. However, before you leave for your trip, find out if you will need to exchange currency.

Sticking to only all-inclusive resorts

nadezhda1906/Adobe two cocktails on luxury beach resort

As with cruising, spending your vacation at an all-inclusive resort takes the planning and coordinating out of your Caribbean vacation. Just keep those fruity and frozen drinks coming, right?

However, you might spend more money than you need to at these resorts. Be sure to read the fine print so you know what’s actually included.

Also, Airbnb and even regular hotels offer some great options that are much cheaper, so check those out too.

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Not taking a long enough trip

luengo_ua/Adobe young man resting under the palm tree

Make sure you book a long-enough trip, even if you’re planning on spending your entire Caribbean vacation poolside with an umbrella drink or lounging on the beach with a book.

It’s good to schedule enough time to account for things like flight delays, jet lag, travel from the airport to your final destination, and traffic delays.

All of these issues can eat up more vacation time than you would expect.

Expecting everyone to speak English

pathdoc/Adobe two funny looking men having troubled communication

Yes, the Caribbean is a popular tourist destination. But don’t assume that everyone in the region speaks English because of that.

This group of islands has a rich history, with a full spectrum of people, culture, and languages, including Indigenous tongues, Spanish, French, and Dutch.

That doesn’t mean you have to learn a language before going, but be mindful that some folks might not know what you’re saying.

Presuming one island is just like the next

Reimar/Adobe signpost of Caribbean islands on the beach at St Maarten

The Caribbean may be one region, but don’t assume the islands are interchangeable. That aforementioned rich history extends to food, pop culture, traditions, and more.

The landscapes of each island are also wildly different, from the old city of San Juan in Puerto Rico to the mysterious Boiling Lake in Dominica.

Even the wildlife varies from one place to the next, from swimming pigs in the Bahamas to green monkeys in Barbados.

Not preparing for Island Time

nito/Adobe man and a stone with a clock drawn in it

Yes, it’s a thing — folks in the Caribbean generally aren’t in a rush. So, if you expect your guides and porters to hurry up, you’re inevitably going to be disappointed.

Rather than resist this slower pace, the best thing you can do is lean into it. After all, you are on vacation. So, expecting your waiter to make a drink faster means you’re not enjoying yourself properly.

Sit back, and let things happen when they happen.

Not exploring the rest of island

Phuong/Adobe paddling kayak on blue sea

What’s better than getting to your destination in the Caribbean to find the resort is gorgeous, the views are pristine, and the food is worthy of a Michelin star?

Not much, to be honest. But don’t make the mistake of staying at the resort the whole time.

You have a whole island to explore, with fun activities, friendly and informative locals, and hidden gems awaiting your discovery. Don’t miss out on a chance to see something new.

Assuming the water is potable

Sundry Photography/Adobe danger non-potable water sign

Like many places in the world, not every island in the Caribbean has tap water that’s safe to drink. For example, you should steer clear of tap water in the Dominican Republic, even for brushing your teeth.

Generally, the best way to approach this is to ask your hosts or guides which water is safe for your health given that you are just a visitor. Otherwise, you might end up seriously sick on your vacation.

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Not planning around hurricane season

drew/Adobe hurricane Delta tearing up the coastline of Grand Cayman

Hurricanes are a fact of life in the Caribbean, and they usually develop between June and November, with August and September being the peak season.

While major storms only hit a few times a year, they can make travel to some islands unpredictable during this period.

Still, you can often score good rates and avoid the crowds during hurricane season, so your mileage may vary. 

Assuming there's cell service

Anucha S./Adobe No Service showing on the smartphone with tropical island background

You’d be hard-pressed to find an American who’s not super-reliant on their phone, but don’t expect to have 5G and high-speed Wi-Fi everywhere you go in the Caribbean.

Sure, you can probably count on your hotel, but that’s about it, especially in remote regions.

If you absolutely need service, consider signing up for an international data plan before you go. But ideally, leave work at the office and relax. Isn’t that why you’re in the Caribbean in the first place?

Not taking taxis

kmiragaya/Adobe typical Cuban coconut shaped taxi in Havana

Some things are best left to the professionals, and that includes driving in the Caribbean. For starters, asking for directions might leave you confused, wondering at which palm tree to turn left.

Oh, and people drive on the opposite side of the road in many parts of the Caribbean. Then there are different traffic rules, and maybe even mountain roads that are barely paved.

You’re probably not going to find an Uber, either, so just sit back and take the taxi. Remember to take your top travel credit card with you if you want to stretch your dollars.

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StockPhotoPro/Adobe man having a staycation and resting on a deckchair at home

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A vacation anywhere in the Caribbean can be a relaxing, adventurous, and overall fun experience for any traveler. Just be sure you avoid making mistakes that can put a serious cramp in your style or have you missing out on something wonderful.

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Cat Lafuente

Cat Lafuente is a Florida-based writer and editor with extensive experience in digital and print content spaces. Her own personal finance journey — particularly consolidating debt and paying it off, in turn boosting her credit score and becoming a homeowner — inspired her to join the FinanceBuzz team; she hopes she can help others do the same.