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My Caribbean “Education”

I’ve learned a lot about traveling in the Caribbean. Luckily, my job allows me to visit the Caribbean islands several times each year. Airline crew workers don’t always get a lot of time off, but it’s really fun to be able to explore and learn about the world’s most popular islands. On my last layover, which happened to be in Nassau, The Bahamas, I had the chance to completely relax for an afternoon on the beach, enjoy the warm sun and take in the fun atmosphere.

Sitting there on my recliner, I started thinking about all the other times I’ve visited the Caribbean and what I’ve learned from those experiences. Maybe the reason it was on my mind is that I was right smack in the middle of one of the top vacation spots on the planet, spending an afternoon in a place where millions of people wish they could be.

In fact, some of the most common questions people ask me when they find out what I do are, “Do you go to the Caribbean? What’s it like? When is the best time for vacations? What are the top cities to visit there,” etc.
So, while I was drifting off to sleep under the warm Caribbean sun and noticing the gentle breezes glance across my skin, I collected my knowledge and thought about what I might say to the next person who inquires about this global playground. It dawned on me that I had learned several lessons about traveling in the Caribbean.
Number one: There’s really no “best” time to go because even in the off-season, from May until November, there are fewer people and lots of bargains. Whether you’re in The Bahamas, Cuba, Jamaica or anywhere else in the island chain, travel season can get a little hectic.

So I think the next time someone asks about the smartest time to go, I’ll say, “Stick to the off-season and you’ll have more fun, get better plane fares and be able to snag more local bargains. The local hotels in the Caribbean compete a lot for business when there aren’t as many people there.
Number two: It helps to hire a local guide from a reputable company or from the hotel where you’re staying. Don’t hire “freelance” tour guides off the streets; you don’t know what you’re getting and might even be putting yourself in danger. Stick with professional, registered travel and tour guides. The cost is super low and worth every penny.
What can a savvy tour guide do? Plenty! They can steer you away from the high-priced tourist traps and show you some off-the-beaten-path hideaways where you can buy great souvenirs, socialize with locals and see historic sites that are often closed to outsiders.

Number three: One trip is not enough! Plan to take at least three trips to the Caribbean in order to sample all the different cultures. Of course, Nassau is one of the top attractions and should be on everyone’s list. But cities like Havana, Santa Domingo, San Juan, Kingston and Georgetown are other must-see spots. I think travelers often make the mistake of assuming that “the Caribbean” is one country with a single culture. In fact, 26 countries make up the island chain and dozens of different cultures are represented.
So if you plan on taking a trip to the area any time in the near future, plan on checking out maybe a half-dozen different cities and countries if you can fit it into your itinerary. Hire a local tour guide in the cities where you spend more than a day or two and consider visiting in the off-season, which typically runs from May until November.