There aren't too many things that are more exciting than booking a vacation. When it comes to bucket-list destinations, the Caribbean is on most people's lists, and for good reasons. With sun-kissed sands, all-inclusive resorts that offer fantastic deals, and short flights compared to many other tropical destinations around the world, there's nothing that's not to love. The only thing that could bring a trip down is making a rookie mistake - such as these.

Before Booking...

Mistakenly Assuming Every Resort Is An All-Inclusive

The Caribbean has gained an extensive reputation for offering great all-inclusive deals, and while the islands are full of these resorts, that doesn't mean every resort is automatically all-inclusive. Before booking, be sure to do thorough research in order to avoid booking an accommodation that might offer meals, but doesn't offer transportation or access to its services.


A resort might also offer access to its excursions and rentals but won't have access to an on-site restaurant or meals. It's important to avoid making this mistake because the last thing any traveler wants is to accrue extra, avoidable costs, or end up without breakfast, lunch, or dinner every day.

Not Doing Research To See Which Island Is Right For You

Sure, all Caribbean islands might have flawless beaches and palm trees but that, by no means, implies that they're all the same. In fact, every single island differs from the next, regardless of whether it's next to another or all the way across the archipelago.

Each island has its own culture, history, and geography, which can make for very different vacations across the board. Everything - from the food to the fun - is different between the islands.

Passing Up Weather Patterns For Great Deals

As much as no one wants to acknowledge it, hurricane season does heavily affect the islands. A tropical paradise can go from euphoric to dangerous in a matter of only days if the weather conditions align, and this is definitely something to take into account when planning a vacation.

If a deal sounds too good to be true, then it probably is - chances are, you'll be booking at the height of hurricane season. Alternatively, booking during the off-season might be worth it, as long as the weather isn't a concern.

Hurricane season: June 1st - November 30th

Related: Looking For A Crowdless Caribbean Vacay? Consider These Islands For Future Trips

On The Island...

Forgetting Cash, Or Forgetting To Research Costs

While travelers are researching which island is best suited for them, they should also be researching the costs of each island. Just as the islands differ, the cost of vacationing in them also differs. A vacation in the Cayman Islands will differ drastically from one in St. Maarten, and so on and so forth.

The cost of food will differ depending on whether it's included in the resort price, street food, or coming from restaurants outside of the hotel or resort. The cost of excursions will differ based on the prices of boat tours, the length, and which activities are available on the island a traveler is visiting. In order to avoid surprises, it's best to hash out all of these details prior to booking.

Neglecting The Fact That Not Every Island Will Have English-Speaking Locals

Surprise! If you were still thinking that the Caribbean is home to an all-English-speaking population then you'd be wrong. Just as each island has its own history, it also has its own language that has been passed down and spoken for generations.

Travelers can expect anything from French, Spanish, or even Dutch when visiting the Caribbean, depending on the island they choose to visit. Knowing a few basic words in the dominant language of the island you're visiting will go a very long way.

Never Venturing Past The Resort Grounds

Some of the best Caribbean destinations exist far outside of resorts and off the beaten path. It's perfectly fine to visit an island and stay at the resort the entire time but will it truly feel like a vacation unless you've seen or done something truly amazing?

Probably not. Resorts can arrange excursions and tours and these are both something to take advantage of. Even wandering into town can be a worthy experience, if only to explore open-air markets and try traditional Caribbean food that might not be on the hotel menu.

Major Take-Aways When Traveling The Caribbean

  • Always research. From all-inclusive resorts to the language that's spoken, a little bit of research can go a long way.
  • Anticipate extra costs. Planning ahead is always better and part of that is carrying a little extra cash than you normally would.
  • Don't disregard the weather. Don't be afraid to take advantage of low deals but be aware of the time frame.

Next: A Guide To Visiting Cayman Brac, The Lesser-Known Gem Of The Cayman Islands