The Caribbean is the perfect vacation destination for those looking for warm weather, endless beaches, and exciting activities on and off the water. From nightlife and water sports to great food and historical attractions, the Caribbean has something for everyone.
However, as someone who’s been traveling to the Caribbean for the past two decades, I’ve observed some common mistakes first-time visitors make.
If you’re planning a trip to the Caribbean and want to maximize your experience, here are some mistakes to avoid making while visiting.
Not leaving the resort
The Caribbean is full of gorgeous resorts, but one of the biggest mistakes I see first-time visitors make is never leaving the property. Every time I travel to an island, I make a point to leave the resort and check out nearby attractions.
One of my favorite recent travel experiences was a day trip in Jamaica, where I was able to float down the Martha Brae River and climb Dunn’s River Falls.
If you’re unsure of what activities are available, check out some reputable tours online or ask your hotel’s concierge for recommendations. If you do plan to leave the resort, be sure to do your research and take standard safety precautions.
Sticking to only all-inclusive resorts
The Caribbean is known for its all-inclusive resorts, which are convenient for families with small children or large groups of friends.
But for solo travelers, couples, and families with older kids, I recommend checking out smaller boutique hotels. Some of my best travel memories have come from staying at smaller properties.
When I visited Puerto Rico for the first time, I stayed in a charming one-bedroom apartment in Old San Juan, which was just a short taxi ride to the beach.
We spent our days exploring Old San Juan, and each night, we chose a new restaurant to visit, which we wouldn’t have done if we stayed at a large, all-inclusive resort.
Assuming all islands look the same
There’s a common misconception that all islands in the Caribbean look the same. However, the geography varies from island to island.
Volcanic islands like St. Lucia and Dominica boast black-sand beaches, Turks and Caicos and The Bahamas have relatively flat terrains and deep cave systems, and Antigua and St. Croix have rolling hills ideal for long hikes.
In Aruba, visitors can relax on white-sand beaches or explore the towering cactus plants, sand dunes, and rocky pools in Arikok National Park.
Each island offers something a little different, and you can maximize your stay by knowing how you want to spend your vacation.
Not island hopping
Although island hopping sounds costly, several locations have convenient and affordable ferries. For example, visitors can take a ferry from St. Kitts to neighboring Nevis to dip in the hot springs or visit the botanical gardens.
I always recommend setting aside a day to check out a nearby island, especially if it’s accessible by ferry.
Expecting a fast-paced lifestyle
First-time visitors to the Caribbean may be surprised to find that, for the most part, life seems to move slower on the islands.
Be sure to leave time between activities or meals and embrace flexibility. If you have activities planned, I recommend doing one activity per day or setting aside at least half a day for each excursion.
In Barbados, for example, I hired a driver to check out Bathsheba, a stunning rocky beach on Barbados’ east coast. On our way back, my tour guide recommended stopping by a popular beachside restaurant, which wasn’t on the itinerary.
I ended up staying for a few hours, ordering food and drinks, and walking along the beach. I would have missed this delicious detour if I had been on a tight schedule, and I always advise embracing the slower island pace for the best experience.
Not eating local food
Part of the joy of traveling is experiencing new cuisine, and the Caribbean offers a variety of food that reflects each island’s history and culture.
In Puerto Rico, I made it a point to eat mofongo, an African-influenced dish made from fried plantain. In Grenada, I tried oil down, a delicious meat and vegetable stew.
On a girls’ trip to Curaçao, we stopped by a local restaurant that had come highly recommended for its goat burgers. I was apprehensive at first, but it was one of the most delicious and memorable meals on the trip.
Not researching the best time to visit
Though the Caribbean offers year-round warmth, some months are better than others for a trip.
For example, although most of the Caribbean experiences hurricane season from June to November, a few islands like Aruba, Bonaire, and Curaçao are outside the hurricane belt.
The summer low season also means lower hotel rates, but it comes with higher temperatures and afternoon rain showers.
Peak season in the Caribbean is in the winter months when hotel rates are premium and rooms can sell out quickly. However, if you book well in advance, you can look forward to spending your New Year’s Eve on the beach.
This story was originally published on May 30, 2024, and most recently updated on June 3, 2025.
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