15 Mistakes to Avoid on Your Caribbean Vacation

A tropical vacation should be rejuvenating, but there are pitfalls that could undo all that relaxation. Learning the essentials about local culture will help you calibrate your expectations and maximize your time enjoying your Caribbean vacation. Avoid these common mistakes for a trip that’s both free of FOMO—by choosing the right destination, for example—and full of incredible experiences suited to your travel style.

Thinking All Islands Are the Same

There are many beautiful Caribbean islands, but don’t fall into the trap of thinking that they’re all the same. For glamorous beach clubs, St. Barts offers plenty of things to do, while wilder islands like Dominica cater to hikers and waterfall chasers. Even the ABC Islands (Aruba, Bonaire, and Curaçao), which are often lumped together, have distinct cultures of their own. And if you think it’s all been done before, you’ll be pleased to know there are off-the-beaten-path gems like Canouan that will surprise you with its luxury offerings. Discounting the unique aspects of each destination or assuming that if you’ve seen one Caribbean island, you’ve seen them all, would mean missing out on a rich and diverse array of culture, food, traditions, and landscapes.

Only Considering All-Inclusive Hotels

Paying one price for your whole Caribbean vacation at an all-inclusive resort can help you stay within your budget, but it’s not always the best deal—and it’s definitely not your only option. From stylish boutique hotels in St. Croix to villas and cottages on the private island of Mustique, accommodations in the Caribbean are as varied and diverse as the islands themselves. If you do decide to go the all-inclusive route, make sure you read the fine print. It would be an expensive mistake to assume that all properties in the region cover room, board, activities, and more. Take a close look at the booking information and know what’s included in the rates.

Not Venturing Beyond the Hotel Grounds

It’s easy to spend your entire trip relaxing at the resort, especially if you’ve booked an all-inclusive vacation. It can be a convenient and cost-effective way to plan your tropical vacation, but if the hotel is your only exposure to the Caribbean (and you don’t include some non-resort offerings), you’ll miss out on much of the flavor of the islands and their enriching cultural experiences. Chatting with locals is also the best way to learn about underrated spots.

Only Visiting in the High Season

High season is high season for a reason. But just because this part of the year has the “best” weather doesn’t mean you’ll have the “best” time. Peak travel time means that resorts are crowded (and competition for the lounge chairs by the pool is fierce). Restaurants are harder to get into, and rates for just about everything are at their max. Especially when you remember that the weather in the Caribbean is generally pretty warm and pleasant year-round, avoiding peak travel times and holidays may be worth it to save money and avoid crowds.

Not Thinking About Hurricane Season

While visiting the Caribbean during the off-peak period has advantages, you’ll likely have to contend with hurricane season, which runs from June to November. Hurricanes are common in the region, but they’re not a guarantee, as many are minor or fizzle out before making landfall. It’s only the occasional tempest that makes headlines and presents the region as a storm-torn bedlam.

So, while you might want to avoid the Caribbean during peak hurricane season from August to October, you might also score a dreamy getaway with all the perks of the off-season and none of the drawbacks. Plus, some Caribbean islands like Grenada and Trinidad and Tobago are located outside of what is commonly called the “hurricane belt,” though they can still experience tropical storms. Whatever you decide, remember that weather is ultimately unpredictable.

Not Trying the Local Cuisine

Most all-inclusive resorts will serve up delicious crowd-pleasers, but you’ll be missing out if you don’t expose your taste buds to the local cuisine. Every island has its specialties, like Jamaican jerk chicken or the Dominican Republic’s sancocho stew. Anguilla, meanwhile, is famous for its award-winning lobster and crayfish dishes, which are enjoyed best when ordered from a local beach shack.

Missing Out on Water Activities

Warm, crystal-clear waters are one of the main draws of a Caribbean vacation, but there’s so much you can do beyond just wading in from the beach. Get close to the magical underwater biodiversity of your destination by heading out on a snorkel excursion. Or, if you want to go even deeper, some resorts offer scuba diving courses so you can get PADI-certified on vacation. If the mask life isn’t for you, you can still get close to the water with sunset cruises and kayaking excursions.

Presuming Everyone Speaks English

While many Caribbean destinations will feel familiar, English isn’t commonly spoken everywhere. You still can get by with English in most places, especially in busy tourist areas where speaking English is a prerequisite for hospitality workers. Spanish is the dominant language in countries like Cuba and the Dominican Republic, but it’s French in Haiti, Martinique, and St. Barts. Dutch is the official language of Aruba, Bonaire, and Curaçao.

Expecting a Fast Pace

In the Caribbean, there’s no getting around it: you’re on island time. Most people would scoff at the concept of a New York minute, and “late” is subjective. Don’t expect things to open when their online hours say they will—think of it more as a guideline. You can choose to get frustrated by it, or you can take a deep breath and realize that the laid-back approach and total absence of hurry are all part of the appeal of kicking back and going with the flow. The only time you won’t want to risk it is when you’ve got a boat to catch because once you miss it, you’ll have to wait for the next one.

Counting on Cell Signal

While many Caribbean islands are populated and modernized, a strong cell signal isn’t a given, and Wi-Fi can be hit or miss depending on which destination you’re visiting and where you’re staying. Some places are better equipped than others, but if you arrive expecting lightning-fast speeds and massive bandwidth, you may be disappointed.

Instead, take advantage of the opportunity to unplug and enjoy a taste of analog life, which in the Caribbean looks like beachfront piña coladas, hearty doses of vitamin D, and hammocks tied to swaying palms—in other words, paradise.

Drinking the Water

Don’t make the unfortunate mistake of drinking the local water before ensuring it’s safe for consumption. It’s a quick way to ruin your vacation, or at least a few days of it. While most of the Caribbean has water that’s safe to drink from the tap, especially at resorts, not all areas do, so be sure to check before you go gulping straight from the faucet. Before traveling, check the CDC Destinations database, which lists health alerts for countries around the world and can key you in on the tap water situation.

Not Looking Up Prices Beforehand

If you head to the Caribbean expecting an inexpensive vacation, you might find yourself shocked at the price points at hotels, restaurants, and stores across the region. The isolated nature of the islands means that most supplies, tools, and ingredients are imported, and you’ll see that tax reflected in the final value of goods and services you’re purchasing. Budget accordingly.

This fact makes all-inclusive resorts even more enticing. Paying one price up front, as high as it may seem to you at home, could save you from an on-island financial freak-out. And while you may think you’d never eat, drink, or play enough to make the price of an all-inclusive worth it, factoring in the inflated prices of just about everything in the Caribbean makes it easier to swallow those steep all-inclusive rates.

Not Carrying Cash

Cash is still king in the Caribbean, so you’ll want to have bills on hand for artisan markets, roadside food stops, and souvenir shopping—not to mention tipping, which is common and appreciated in the service industry. Many islands accept the U.S. dollar, but do a little investigating to determine if your destination warrants securing some local currency, too.

Buying Tacky Souvenirs

In the Caribbean, you’ll be faced with ample opportunities to buy things you don’t need. Instead of filling your suitcase with low-quality tchotchkes, find a market where you can support local artists and makers, like Irie Life in Anguilla or Caribelle Batik in St. Kitts, for authentic and high-quality sarongs and shirts. You (and your loved ones at home) will get a lot more value from things like homemade Jamaican jerk seasoning, Bahamian straw bags, and Barbados rum than you would from a generic T-shirt or key chain.

Assuming a Cruise Is the Only Way to Visit Multiple Islands

Cruising the Caribbean can be a great way to visit the region, but it’s not the only option. It’s possible to see multiple islands on your own schedule rather than being transported from port to port. Hopping between Caribbean islands usually involves a ferry or short flight, and is doable if you’re willing to do a little more heavy lifting on the planning side. Remember that the Caribbean is an umbrella term for a region composed of hundreds of islands across different countries, many of which you can’t get to by cruise ship.