These Travel Hacks Will Make Your Caribbean Vacation Smooth Sailing

With destinations all across the Caribbean open and ready for your visit, there's a lot to keep in mind to make your trip a success. That's why we compiled all those things in one place for you here, so if you've even remotely considered a Caribbean vacation, then scroll on down.

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Staying within the Confines of an All-Inclusive Resort

Yes, the Caribbean is home to many of the world's best all-inclusive resorts and yes, you'll be missing out on most of the Caribbean if you choose to stay in a resort without leaving the entire time you're there. From a short weekend hop to Puerto Rico to a month spent unwinding at an all-inclusive resort in the Dominican Republic, it's essential to get out, meet some locals, and see things.

Oftentimes we find unique accommodations for a great price, such as jungle glamping on the Riviera Maya. It can make more sense to plan on bringing your own food or planning to eat at local restaurants than to restrict yourself to only staying at all-inclusive resorts. This way you're almost sure to have a more authentic experience and, let's face it, after a few days of unlimited drinks and often sub-par food, you get kind of bored and don't always feel that well. If you're set on the all-inclusive route, though, we urge you to plan some time outside the resort.

Assuming that All Accommodation Options Are All-Inclusive Resorts

As we've already established, there are lots of all-inclusive resorts throughout the Caribbean. There are also lots of great resorts that aren't all-inclusive.

It might sound obvious, but when you're booking a place to stay, make sure to verify what's included — it could prove to be expensive, or at least inconvenient, not to. If something is unclear, it's best to reach out before booking if the booking is non-refundable and before the free cancellation date if it's fully refundable. Also make sure that the fast internet that you see advertised is actually included in your rate, as there are some resorts across the Caribbean that charge for it.

Expecting Everybody Living There to Speak English

Don't get us wrong, English is the native language of lots of Caribbean Islands, and it's certainly the most common second language — lots of locals will speak it. At the same time, lots of locals don't speak English, so planning for that is the way to go.

We all know that learning the local language is the best way to go, and it's always minimum effort to at least get a hang of basic words. That said, it's probably not practical to learn an entire language for a shorter trip in a month. So unless you're up for the challenge, we recommend downloading Google Translate along with the language(s) for offline use you'll need to communicate. A physical dictionary, though bulkier, can be a fun tool for bonding over a game of pointing at words with locals as well.

Forgetting to Plan for the Sun and the Water

Let's cut to the chase, the sun and water is probably what brought you to the Caribbean in the first place, so letting it ruin your trip would just be... sad.

Reef-friendly sunscreen is easy to find pretty much everywhere in the Caribbean, but bringing it from home works too. Apply it early, and keep applying it throughout the day. We've yet to find a sunscreen that really does its job after a few hours, so instead of finding out if it really works like it says or not, just make putting it on a ritual.

As for the water, you want to come prepared with the things you need to go in. Bathing suites and towels are obvious, and maybe you don't even need to the towel, depending on where you're staying. Things you might not have thought of include not just goggles and beach balls, but also making sure you've got the proper training to do what you want to do on your trip — especially if you don't have weeks to spend learning to dive, or taking snorkeling lessons.

Taking Cell Signal for Granted

This one isn't exclusive to the Caribbean, but when you're in the middle of the sea it's good to plan ahead. You'll find that most heavily populated areas have decent cell signal, but lots of the pristine beaches, picturesque jungles, and other neat things that you'll want to experience aren't near those areas. So if you're planning a work-ation or hope to have a family Zoom call from what is effectively the middle of the sea, it's usually best to think twice.

Depending on where you are staying, you might also find that the Wi-Fi is less than adequate. You can usually search through reviews of where you plan to stay beforehand to see what people say about the internet connection there, though if you're looking to go somewhere far off the touristic map you may want to have a back-up plan such as a portable satellite internet connection. Another option is getting a local SIM card that allows you to make a hotspot if cell phone service works where you'll be staying.

Our most sure-fire hack to keep from getting completely lost is to always have both a local map and an offline download in Google Maps. That said, it can also be nice to let yourself get lost a bit once you gain some familiarity with a place.

Drinking Tap Water without Asking First

This one could easily ruin your trip for a few days. Our rule of thumb is to always ask if the tap water is potable before drinking. Lots of places in the Caribbean have awesome tap water, but lots of places have tap water that could make you very sick (looking at you Cancun). It'd be a shame to create all the unnecessary waste that comes with only drinking bottled water, but many accommodations offer filtered water that you can refill bottles with, and there's always those massive eight liter water bottles that at least cut down on plastic waste if nothing else.

Buying Everything from Tourist Shops

We're not telling you not to give tourist shops your business. But hurrying to the first tourist shop you see to buy all the beach necessities could prove to be a pretty expensive mistake.

It's one thing to pay for convenience when you forget something small, but the inflated prices most of these shops charge generally outweigh the hassle of planning ahead by bringing what you already have at home, or finding out where the locals go shopping. Beyond the necessities, a little bit of effort made to shop with the locals goes a long way for the avid souvenir hunter.

Forgetting About a Little Thing Called Hurricane Season

We don't need to tell you that you probably don't want to spend your trip in the Caribbean dealing with a hurricane.

For shorter trips, peak hurricane season can actually mean a great way to save because off-season rates are typically much less — specifically for travel from mid-August to late September. The catch is that you want to be very flexible with that kind of trip, so that you can either change your dates last minute or alter your plans to avoid stormy weather.

Moreover, some Caribbean islands are located outside of the hurricane belt — Barbados or Grenada being two examples. If you're traveling during hurricane season, you always want to keep an eye on the weather, but ruling out travel altogether could mean missing a lot of great chances for awesome budget travel.

Additional Information

Check out our destination guides for more insight on your trip to the Caribbean (or anywhere else for that matter).