11 Rookie Mistakes to Avoid on Your Caribbean Vacation

See recent posts by Megan Wood

Beach at the Anse Chastanet Resort Beach at the Anse Chastanet Resort; Laura Hinely/Oyster

Most Americans fantasize about escaping on a sunny Caribbean winter break every year. Just thinking the word "Caribbean" conjures of images of white beaches, crystal clear water, tropical fruit rum drinks, and sun-soaked days. If you're actually headed south for a Caribbean vacation, you're in for a treat. But, it's a diverse part of the globe and there's lots to keep in mind. We’ve visited every Caribbean island multiple times (it's okay to be jealous), so we're here to help you avoid making any major rookie Caribbean mistakes. Before you book your tickets to paradise, read on.

Editor's note: Save these Caribbean travel tips for the future, and always follow the travel restrictions and quarantine rules of the country you plan on visiting. 

1. Assuming Every Caribbean Island Is the Same

If you’ve been to one Caribbean island, you might wrongly assume you’ve been to them all. But that’s a rookie mistake. The Caribbean archipelago contains three main island groups: the Lesser Antilles, the Greater Antilles, and the Lucayan Archipelago, which includes the Bahamas and Turks and Caicos. These islands are technically in the Atlantic, but have important ties to the Caribbean. There are 13 sovereign island nations and 12 dependent island territories with political and financial ties to Europe and the United States. Still with us? Another 10 Latin American countries have Caribbean coastlines, and the islands along the coasts of Central and South America usually get included in this group as well. Long story short, each Caribbean island has a distinct history, topography, government, culture, and economy. For instance, Aruba is located just off the South American coast. It has a desert-like topography and is a constituent country of the Netherlands. Compare that to the rain forests and Spanish Colonial buildings in the American territory of Puerto Rico. Let’s not forget that the Caribbean consists of more than 7,000 individual islands, though the vast majority of these are tiny and uninhabited. All in all, the Caribbean goes way beyond cruise ship ports. 

2. Expecting Every Hotel in the Caribbean to be a Budget All-Inclusive Property

We get it, you want to save money on vacation. And there are definitely some incredible Caribbean all-inclusive deals to be found. But please remember that the Caribbean relies heavily on importing food and goods from other countries, which costs time and money. Labor is also cheap in the Caribbean, and many resort and tourism employees depend on tips from guests to supplement their incomes. The Caribbean is also home to some of the most beautiful luxury resorts on the planet, and all that prime oceanfront property and well-designed architecture has a hefty price tag, even in Caribbean countries with small economies. That said, there’s a whole range of hotel and resort prices, and you generally get what you pay for in the Caribbean.

3. Depending on Cell and Wi-Fi Service in the Caribbean

You’re probably in the Caribbean to relax and enjoy your vacation, so concerns about your Wi-Fi signal should be minimal. But if you’re addicted to Instagram and email (we’re definitely guilty), we have some bad news. On less developed islands, most beaches, up in the mountains, deep in the rain forests, and on almost all boat excursions, you likely won’t find a signal unless you’re paying for an international plan on your phone. Of course, capital cities and most hotels will have Wi-Fi (sometimes free, sometimes not) so it’s not like you’ll never get online. If you need navigation, download maps before you get on the plane. Note that you can plug in your charger and any other dual-voltage devices in your hotel room. In fact, some islands use U.S. standard current (110v), and many individual hotels have installed 110v plugs in guest rooms.

4. Assuming Everyone in the Caribbean Speaks English (or Spanish)

6. Forgetting About the Caribbean’s Hurricane Season 

Did you find a crazy good deal on a flight or hotel room in the Caribbean from Mid-August through late October? Well, that’s probably because it’s peak hurricane season—when intense thunderstorms near the Equator drift over the Caribbean’s warm waters, giving hurricanes the ability to develop. That’s not to say you should avoid the region entirely during that time period. Hurricanes hit where the water is warmest, which scientists can map and track. But, travel insurance is a good idea. To really hedge your hurricane bets, consider booking in the far southern Windward Islands (Trinidad and Tobago, Grenada) and the ABC Islands (Aruba, Curacao, Bonaire) which are below the hurricane belt. Central American Caribbean countries also tend to stay hurricane free.

7. Spending Your Entire Caribbean Vacation on the Resort

We fully understand the siren songs of a private beach, unlimited breakfast buffet, and all-inclusive cocktails, but spending your entire Caribbean vacation at your resort is a major rookie mistake. Caribbean destinations offer everything from snorkeling and boat excursions, to mountain trekking, to thriving cities with glamorous nightlife. Oh, and then there’s zip-lining, horseback riding (right in the ocean in Jamaica!), mountain biking, underground caving, volcano treks, and bird-watching. Don’t let fear (or laziness) keep you chained to your pool chair.

8. Planning to Drive in the Caribbean

Barbados street
Barbados; Laura Hinely/Oyster

We’re not saying you can’t rent a car in the Caribbean, we’re just telling you to think twice. First things first, many islands are former British colonies and people drive on the left-hand side of the road. Looking at you: Jamaica, Antigua and Barbuda, Barbados, Dominica, Grenada, Saint Kitts and Nevis, Saint Lucia, Saint Vincent and the Grenadines, Trinidad and Tobago, and the Bahamas. Second, roads aren’t always well maintained or signed and you might be sharing them with enormous local busses and tour busses, plus motos, cyclists, and pedestrians. Take our advice, pay for a shuttle service, and leave the stressful driving to professionals who get paid to handle it.

9. Being Afraid of Locals in the Caribbean

Bad things can happen to good people anywhere in the world. That’s just a fact. And outside of a few neighborhoods and capital cities in the Caribbean, the region is by and large very safe. Of course, you should use common sense and practice smart safety practices, but don’t let fear keep you from chatting with the people who live on the islands you’re visiting.

10. Assuming You Need a Visa to Visit the Caribbean 

Americans, you’ll need a valid passport to enter any of the Caribbean islands (except for Puerto Rico and the U.S. Virgin Islands)—and to get back in the United States. Most non-U.S. islands also require a return or ongoing airline ticket. But you don’t need a visa.

11. Buying Single-Use Plastic Bottles and Wearing Regular Sunscreen in the Caribbean

Climate change is already impacting the Caribbean. Supporting organizations and politicians who take a stand against climate change is the best way to help, but there are other proactive measures all Caribbean visitors should take. First, say no to single-use plastic water bottles. Bring a reusable water bottle and refill it as needed. If you must sip piña coladas with a straw, consider packing a metal version. And if you plan on swimming, snorkeling, cliff-diving, or scuba diving, reef-safe sunscreen is a must. Coral reefs are dying at a rapid rate and one of the major contributors are the chemicals oxybenzone and octinoxate found in many sunscreens. Luckily, there are better alternatives. Blue Lizard is a reputable brand that will keep your skin (and the coral) safe. Our Caribbean Hotel Picks:

Our Budget Caribbean Hotel Pick: Majestic Colonial Punta Cana Resort in Dominican Republic

Aerial Photography at the Majestic Colonial Punta Cana

The Majestic Colonial consistently tops our lists for the best budget-friendly and most bang-for-your-buck, thanks to its beautiful beach setting and all-inclusive rates that stretch through six restaurants, 11 bars, premium liquor, beach loungers, sports facilities, entertainment, snorkeling, and kayaking. Suites have jetted tubs, free minibars, furnished terraces, and rainfall showers. Oh, and there’s a kids’ club and multiple pools. Phew! That’s a lot of value.

Our Luxury Caribbean Hotel Pick: The Ocean Club, A Four Seasons Resort, Bahamas

The Ocean-View Pool at the The Ocean Club, A Four Seasons Resort, Bahamas

There’s nothing quite like The Ocean Club, A Four Seasons Resort. It’s on Paradise Island, so guests have access to the amenities at The Atlantis (but none of the crowds). The 105 rooms and suites feel intimate, but are incredibly luxurious, with features like iHomes, free beach accessories, private balconies or patios, and massive bathrooms with steam showers and soaking tubs. Expansive grounds feature three outdoor pools (including a beachfront infinity pool), statuary modeled after Versailles, and the white-sand beach. Throw in free yoga classes on an oceanfront deck, an 18-hole golf course, an indoor/outdoor fitness center, a Balinese-style spa with private villas, and free bike rentals. After a day exploring, guests return to free Champagne and strawberries. Sunset drinks are on offer at Jean-Georges Vongerichten’s Dune restaurant (the celebrity chef’s first Caribbean venue).

Our Couples Caribbean Hotel Pick: Jade Mountain Resort in St. Lucia

Celestial Terrace at Jade Mountain Resort

The Jade Mountain Resort in St. Lucia was built for romance. The 29 enormous suites, called sanctuaries, are breathtaking. Each has an open fourth wall with a view of the water from the canopied bed, raised whirlpool tub, and (in all but the entry-level category) private infinity pool. For those who can pry themselves out of their rooms, it’s a short shuttle ride or hike to two beaches, free water sports, and a dive center. Organic cuisine is served from a chic open-air restaurant. Guests can expect blissful peace and quiet throughout the property. No TVs and no kids allowed.

Our Family Caribbean Hotel Pick: Beaches Negril Resort & Spa

Aerial Photography at the Beaches Negril Resort & Spa

Beaches Negril Resort & Spa is a beautiful property with a wide variety of activities and facilities for the entire family. It sits on a wide stretch of the lovely Seven Mile Beach, and has tons of water sports available. There’s also a water park, kids’ camp, teen hangouts, and specialty activities. Parents can utilize the spa or candlelit dining for two. A wide variety of room options are available, though all are spacious and contemporary, and have terraces, iPod docks, and coffeemakers. Dining options are also plentiful and kid-friendly, with standouts including sushi, Italian, and frozen yogurt options. Kids and parents won’t want to leave.

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