How to Make the Most of Your Next Trip to Cuba

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Next month over the Thanksgiving holiday, I’ll be leading a group to Havana with School of Visual Arts colleague Jaime Permuth for a week long exploration of the capital city and the surrounding area. Our last trip was fantastic. I’ve been going there for years, but I was amazed we were able to photograph things I hadn’t ever seen.

Now that everyone is talking about going to Cuba, the question you might ask is:

Would such a trip be right for you?

I would ask it a different way. If you’ve never been part of a destination photo workshop before, the better question might be:

What kind of a visitor do you want to be?

Your experience could be wildly different from someone else, depending on the answer.

I’ve experienced Cuba in very different ways. I was a family member looking to reconnect. I was in a months-long people-to-people exchange. I was a student in Havana. I worked in a news bureau. I led a New York Times Journeys in which I gave hour-long talks ranging from revolutionary photography to Cuban healthcare. Now I’m leading groups for SVA. So I’ve seen and experienced Cuba in different ways and through the eyes of visitors alongside me.

As a visitor to a country, do you enjoy a little bit of surprise and risk or do you want everything planned out?

Do you seek to “get in there”, or do you keep a safe distance?

Are you seeking creative opportunities or more rigorous intellectual stimulation?

The New York Times Journeys trip I helped lead earlier this year was by most measures rigorously intellectual. Everyone was ushered around to a schedule of speakers in a big, modern air-conditioned tourism bus with a Cuban guide who spoke on many topics. It was a comfortable, safe, experience. Meals were pre-arranged with tables waiting for us when we arrived, facilitating discussions. The group was an older crowd, smart and very well traveled. We had amazing access to officials. The group asked good questions, and were fascinated to know more.

But for some it lacked flexibility and the time to explore on your own, to see and meet people on the street or in their homes. You often heard: “Let’s go! The bus is leaving!”

The SVA trip a few months later was very different. With photography being the priority, it was more experience-driven, rather than intellectually-driven. The SVA goal was to get you seeing, talking with, and photographing the Cuban people in real-life environments. You are in the streets and in people’s homes, making friends and learning the realities of the Cuban experience with your camera.

I have a cousin there who is a producer for commercials and music events, so she draws on her network of contacts to make things happen. Visiting a ballpark and getting access to a dugout (during a game no less) was not originally on our schedule, but for a few participants that’s all they wanted to do. So we made it happen.

One participant on our last trip needed help finding a long lost family member. My cousin and I helped to connect them in the evening and it was awesome. I absolutely related to seeing the family ties that bind.

But perhaps the most instructional moment for me, which also motivates this post, was watching one participant in our exchange jump onto the back of an open-bed truck with a big group of guys to have a photo made.

It was a hilarious moment. Everyone in the truck went wild to have their picture taken with him (it might have helped he was wearing a Yankees cap). You just don’t expect a tourist to climb on the back of a truck and to rev everyone up for a group photo.

As a photojournalist, I’m using to keeping something of a professional distance between the subject and me. (As a group leader, I was afraid the truck would take off, leaving one less student). It’s my fly-on-the-wall orientation.

But my friend blew up that distance and my concerns, showing me something I had forgotten about any cross-cultural exchange.

We’re all mostly looking for moments that bring people together – to forget our differences and the monotony of day-to-day life. If it’s a crazy, unexpected spectacle, all the better. Months later, I still think about that experience and smile at the joy it brought everyone.

Will there be another such spectacle on our November trip?

Who knows, but when it comes to making the most of any trip to Cuba, it’s your readiness to enjoy the unexpected that can make all the difference.