Travel Insider: How to Travel to Cuba Today

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Canadian cruise line operator Cuba Cruise recently announced that American travelers will be booking tours of Cuba. Now that you can (legally) travel around the island by land, sea, and air, you need to know how to do it right. To avoid any mishaps with regulations, it’s best to connect with a travel agency such as Insight Cuba. The New York-based agency has made Cuban travel for U.S. citizens possible since 2000. Kara Cragin, a Cuba group tour specialist at Insight Cuba since 2003, spoke with us about what needs to be on your Cuban to-do list, how to make sure you get your fix of Cuban cigars, and what you need to know about traveling to a once-forbidden island.

What is the biggest mistake people make while booking a trip to Cuba?
People automatically assume Cuba is going to be inexpensive. Most things in the service industry are imported and prices for U.S. travelers are generally more expensive. There are bargains in Cuba but you need to know where to look. Also, do your research and choose a U.S. company that is experienced in Cuba. Traveling to the island is unlike traveling to most destinations and an experienced Cuba tour operator pays off dividends.

What is the number one thing people need to plan for when traveling?
Since U.S. credit and debit cards don’t currently work in Cuba, it’s important to plan to bring sufficient cash with you. People-to-people tours cover many expenses but if you like artwork, cigars, and nights out, you’d be surprised how quickly you can spend money.  

When you are booking a trip to Cuba, what are the most important things to consider?
Bring flexibility and patience. Cuba is a developed society but it does things in its own way. It’s part of the charm and beauty of the country and its people. Also, when you are speaking with an agent or tour operator, you should feel as though they know what they are talking about. Working with someone experienced in Cuba is important so you know what to expect and how to maximize your experiences.

What’s it really like to be in a country that was once illegal to travel to?
The first time I stepped out of the airport into Havana, I felt like I was walking into a movie. The old cars were zipping around and Cubans were hanging out in big circles as if they were all family. There were moments where I felt like I had stepped back into time and was in Paris or New Orleans, but then I’d see a Cuban walk by smoking a cigar and I’d remember where I was. If I had to describe Cuba in one word, I’d use the word nostalgic.

What's your top piece of advice for travelers?
Don’t be shy. Cubans are warm and welcoming. Engage with people you meet.