How to be ready when the travel doors open to Cuba

Tom Popper, President of Insight Cuba, has been a guest on TravelTalkRADIO and BusinessTravelRADIO throughout the years and has already taken thousands of people to Cuba through the People to People p

How to be ready when the travel doors open to Cuba

Tom Popper, President of Insight Cuba, has been a guest on TravelTalkRADIO and BusinessTravelRADIO throughout the years and has already taken thousands of people to Cuba through the People to People programs. Tom has also completed extensive work to “be ready” when the doors open easily and wide to Americans. He has information and hints on how to best tour this amazing little island.

Here, TravelTalkRADIO shares the interview with Tom conducted by Sandy Dhuyvetter, who also runs BusinessTravelRADIO:

Sandy Dhuyvetter: Welcome back to TravelTalkRADIO, my name is Sandy Dhuyvetter. I get so excited when I get to talk about something that means so much to me, and when we think about Cuba, how long have we been waiting for this opportunity to travel to Cuba? And plus, when you find a company that can provide everything for you, and when you know that there’s still some, well, questions about going because this is all a new experience, especially for us Americans. Well you couldn’t be situated in a better place than to be with us this morning. I’m talking to Tom Popper, he is the president of Insight Cuba. I’ve had the opportunity to have him on the show almost regularly now, and I’m loving it because there’s so much to learn, there’s so much excitement. We’ve got a lot of mass media coming into the play talking about what’s going on, and we want to get to you exactly what you can expect, what’s going on now, and of course, what we will look for as we go down this path of coming to Cuba, and of course getting closer to this, this really such a close neighbor and it’s so exciting. So let’s bring Tom Popper in, we’re going to get more information on the news of Cuba, and I’m telling you, if this is on your bucket list, pull up a chair, grab some popcorn or a cup of coffee, or maybe it’s beer, and let’s explore. Tom, thank you for joining us.

Tom Popper: Sandy, it’s always great to be with you.

Sandy: Oh it’s great to have you on the show too, I learn so much, and I get so excited, especially as we talk, and then when we’re through and I set up all the edits and the archives, I just, I still get very excited about Cuba, and I know how hard you have worked for the last many, many years making this happen. So, you must be just tickled beyond belief.

Tom Popper: These are absolutely extraordinary times. And for American travelers to finally be able to go see a country that is so close to us historically, geographically, and culturally, and it’s also a wonderful time for Cubans because there’s so much change going on on the island. But for the traveler, you know each traveler that goes down, they’re part of history, they’re part of a renewal, or a new era in Cuba and with relations between the US and Cuba, so it’s an extraordinary time to go visit the island.

Sandy: You know, I have to ask you something. You know, you got involved in Cuba a long time ago, what was that first spark that told you Cuba was going to be on our radar?

Tom Popper: It was really, you go to Cuba and I think almost everybody visits the island with this stereotype in mind. They have a vision, and part of that vision has been shaped for fifty years, whether it’s the Cuban Missile Crisis, or the Bay of Pigs, or that it’s a communist, socialist, country. “Is there a lot of military, will I be able to walk around freely, am I going to have open and honest discussions?” I’ll tell you the first time I went there I envisioned military being there when I got off the plane, and I kind of had this sense that the sky was going to be grey. But it was extraordinarily curious, and what fascinated me, and I think fascinates every single person that gets off the plane, it’s the total opposite. It’s a bright culture, it’s absolutely sunny—you’re in the Caribbean, but immediately you have, it’s almost like a tickling in your stomach that you’re so happy to be there and to step on Cuban soil and you can’t believe you’re there, and as you make your way from the airport to Havana, and you meet the people, and they’re so happy and so welcoming and so warm, and you kind of see their culture on display; whether it’s music, and how they celebrate children, and their dancing, and all of a sudden you realize “Wow, I’ve been in the dark all these years and there’s this incredible society, so close to us, and I’ve never known about.” So it’s an extraordinary discovery.

Sandy: It’s so interesting as a world traveler, I think of myself having to go to the Middle East, to Africa, to China, to really experience a different culture, but from what you’re saying, it’s ninety miles off our coast, right? (laughs).

Tom Popper: You know you hit it right, that’s so well said. You do, we often think we have to go long distances to kind of go to something different, find something unique. Whether it’s Asia or the Middle East. You’re right, you know, we have this place that has been preserved, the culture has been preserved for so long, and it has all of those elements that the traveler finds fascinating, whether, you know, it’s talking to the people, and how they live, and their society, their music and art form, and Cuba is so rich in these things. These last fifty years, they’ve embraced it, and it actually has propelled their culture and their society. So again, it just makes it a wealth of discoveries.

Sandy: You know, we have lots to talk about. Because, certainly, you know, the world is opening up for us, but still, we have to march to a different drummer rather than if we’re going to go to a different destination. As an American, we’re still—as Americans I should say, we’re still opening up that door and there’s nobody better to open up that door than Tom Popper, and of course his team at Insight Cuba. You can go to Insight Cuba at, and there you’re going to find a lot of information, but what I would totally recommend is sign up for the newsletter, which I’ve done, and I really enjoy that Tom, you really give us a lot to chew on, on that.

Tom Popper: You’re so kind, you’re so kind. We, in addition to considering ourselves, or trying to be experts in travel to Cuba for people that call us; whether they’re inquisitive, or they actually want to go, we try to disseminate as much of that information to the public, whether it’s through our blog, our website, through our newsletter, because travelling to Cuba is confusing for so many people. It is the only country in the world that there are restrictions on American travel, and these are US restrictions, these are not Cuban restrictions. Cuba welcomes Americans with open arms and always have. But, we’re not used to travelling to a country with restrictions. You can travel to Iran, you can travel to Syria, you can even travel, from the US side, to North Korea, but Cuba’s always, well at least for the last fifty years, has been different. So we try to make it easy and make it clear for people so they can, they can make the best decisions and can make the best travel plans possible.

Sandy: Wow, so awesome. Well we’ll take a quick break, we’re going to come back with Tom, and we’re going to talk a little bit about how we can get to Cuba today, tomorrow, whenever you want. So, we’ll discuss that.

Tom Popper is the president of Insight Cuba. We’re talking about travelling to Cuba, can you believe we’re actually talking about that now? And Tom, wasn’t that interesting, the president of Cuba going to the Vatican, to personally thank the pope for, you know, making that transition more smooth for the US?

Tom Popper: It speaks volumes, and it’s just one more piece of news that’s just incredibly exciting and, and it goes to show that, you know, the Cuban government as well as the Cuban people are just so excited about renewed relations, and we see it on the ground all the time. You know Cuban people, they greet us so openly and so warmly, and they’re always making sure that we understand that Cubans and Americans will always be friends. We just need to get past the policies that have divided the two countries for so long so it is, it is, it is so fun, and so exciting.

Sandy: So neat. So let’s get down to brass tacks. Let’s say that we are very interested in going, and we want to go maybe even this summer, or this fall. Tell us what we would need to think of, the requirements, and from your point, what should we be doing to consider our plan?

Tom Popper: It’s an excellent question. You know the first thing I tell friends and family, or whoever else that wants to go to Cuba is, you know, that it’s important to remember that the US embargo against Cuba and the ensuing travel restrictions that result from that are still in place. That the announcements in December and January changed a lot, and they’ve loosened the restrictions, but they still remain, it’s not the type of destination where you can just buy a plane ticket on Expedia or Travelocity and go and book your hotel online, and “viola” you’re in Cuba. The fact that you can’t do that, in many ways make the destination more special. But what’s important for people to understand is that there are twelve categories of travel, which means, as an American, if you fit into one of these twelve categories, you can legally go to Cuba. The categories include if you’re going to visit family on the island, so if you’re Cuban-American and you have an aunt or an uncle, or a child or a parent you can go. If you’re a journalist, you can travel to Cuba legally. If you’re a government official you can. If you’re doing professional research you can travel to Cuba or if you’re going for religious reasons. The thing is with those, at least eleven of those categories, is they’re very narrow in scope. They don’t, as many listeners probably saying, “well that doesn’t affect me.” But there was a game changer that was really introduced originally back in 2000, which is when Insight Cuba got started, but also it was reintroduced in 2011, and it’s a category called people-to-people travel. Why it’s a game changer is it literally allows any American to travel legally to Cuba. The catch is that they have to go with an authorized tour operator company that provides authorized activities. So people say, “What does that mean?” What it basically means is that it’s a guided tour, but guests are going to have unique access to people and places that the average tourist doesn’t see. And part of that is because of the regulations, and the types of activities required, they want rich activities between Cubans and Americans. But what’s fascinating about this, to those of us who love to travel, and those who travel with us, is the experience when one travels always goes back to the encounters that people have with local residents. Whether you’re in Paris, and you’re going to have bread in the morning, maybe it’s the relationship you form with that person. We’ve taken that element of travel, and expanded it. And what ends up happening for guests is they just have incredible experiences, in real life settings with Cuban people, whether it’s musicians and artists, and professionals, who are so wanting to share what they do and how they do it with our American guests, and they want to learn about how we do similar things. They want to learn about our way of life, and we want to learn about their way of life. And in addition to having these incredible experiences, you know, Insight Cuba and other organizations, we take care of arranging those experiences which are not easy to come by, but we also take care of everything else, including hotels, and meals, and flights. And we take a destination that’s very complicated for most people, and we make it very easy.

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Sandy: You know, when you talk about people-to-people you’re obviously going to then interact with the people of Cuba, what kind of a database do you have? I mean, what do you do to go out and meet those people that you, you know, help welcome the Americans?

Tom Popper: That’s such a great question. So in the past fifteen years, we’ve been in Cuba for fifteen years. We’ve built up a wealth of relationships and we cherish those relationships and they cherish us. And even when we started in today, it’s literally we have tour leaders that are on the ground, we have people that are walking around cities and towns all across the island. And when we find something that’s fascinating, we try to incorporate it into our schedule. There’s this great activity that we provide and it’s this home for seniors. And when we think of a home for seniors, we think of a nursing home. But this is a cultural home. And it’s this, it’s this house in a middle class neighborhood, where the local community gets together. And the house is, the best way to describe it, it’s very funky—it has Cuban things from the ‘40s and the ‘50s, and American things from the same time period. But they come together Thursday, Friday, and Saturday nights to dance and sing and play music. And it sounds simple, but they do this, they’ve been doing this for decades. And a friend of a friend introduced us to the person who organizes it, and we’re fortunate enough to bring our groups, and we have video of just huge smiles and people singing at the top of their lungs, and dancing and hugging and swirling around. And, it’s just, the memories that people have from this type of moment, or these types of experiences are incredible. But it’s a constant process. We’re constantly looking for, for new special things for people to see and do.

Sandy: Yeah, it’s just, it’s just amazing to me to listen to listen to all of this, I cannot wait! You know, we’ve got to take one more break and we’re going to bring Tom back. And we’re going to talk a bit more about what you consider, and maybe think a little bit outside the box here.

I don’t know about you, but my bags are getting packed as I listen to Tom. And we’re talking about Tom Popper here, he’s with us from Insight Cuba, the president. And you know, when you think about it Tom, fifteen years that you’ve been working in Cuba, you certainly do know that island. I am sure, inside and out. So what better way to go than to get a hold of you? Now, I want to talk about that next step. Let’s say we’ve decided we want to go. Do we contact Insight Cuba at, or do we go to our travel agent and say we want to go through you? Or, how does that work?

Tom Popper: We try to make it as easy as possible, so it’s really anybody’s preference. They can certainly contact their travel agent, who’ll be able to work with our team here in New York. Or they can contact us directly at Or they can call us at our (800)450-8303, and what’s wonderful about a phone call is we have a team of travel specialists who are all experts on Cuba. They’ve been to the island, they know the island, many of them have led groups throughout the island. So, they can’t answer even the most remote question for our guests. And, there are so many questions about travel to Cuba because so few people have met or known somebody that’s travelled to Cuba and this is all new. So, you know, how you can get there, and what happens when you get there—all those questions can be answered. But what’s also great about contacting our organization is you have choices available to you. And, as you mentioned in the fifteen years we’ve been doing this, we’ve tried to perfect every type of tour we have. We have six signature Cuba tours, which is really the best of the best. In our fifteen years the activities that we love, that our guests love the most, we’ve kind of distilled them and incorporated into something that we know, or we think that every guest will cherish, and there’s six of them based on length of time people want to spend in Cuba, their budget, and even some focus areas and themes. We have jazz in Havana so those people who love jazz and music can focus on that. If somebody wants to travel in two weeks across the island, they can do that as well. Then we also have this series of specialty Cuban tours, which are focused around events or festivals in Cuba, or maybe just a special tour that we’re only able to offer on a limited basis, including the Havana marathon; the Havana art biannual. And it happens every two years in the city of Havana. The city becomes a giant, international art gallery. It’s one of the most fascinating things I think I’ve ever seen. No matter if you walk down an alley or a highway, or whatever it is, somehow, some way, there’s an art instillation or art display, there for you to appreciate. And the artists come to the city, and it’s just the whole city becomes focused around art. So there’s many different choices, and many different ways for people to travel to Cuba, and we help them decide.

Sandy: You know, I have to mention to you, I was talking to some dear friends, and one of them had actually been stationed in Cuba, and he was, he said one of his dreams is to go back to Cuba. Have you thought about, or are you working with folks that have served in the military that want to go back and see what it’s like now?

Tom Popper: That’s another great question. And the answer is yes, absolutely. We’ve had people from the defense department, the military, that travel to Cuba and what’s extraordinary, is, you know, the Cubans, the Cuban government often asks us to let them know because they’re so happy to receive them and show them what Cuba is like. They want to make a special effort to say hello which is kind of neat. We have people that have been on Guantanamo, we have people that served in the military many years ago. So it is a remarkable experience for them as well.

Sandy: When you talk about those, that generation, some of them are a little older now. Is it accessible to get to Cuba? I mean is it an easy—can you provide, I should say, accommodations that are accessible?

Tom Popper: Most of our travelers are 50+ years old. The average age is about 63. The, we do, try to accommodate as many guests as possible. We just ask them to share any special needs that they may have. Cuba is not as accessible as many other countries, it’s just isn’t yet. A lot of the streets are cobblestone, a lot of restaurants are upstairs, accommodations in the provinces often require a walk upstairs. So it, for those people who might have mobility issues, we just ask that they consult with one of our travel specialists, they can really advise them as to which tour might best fit them based on their needs. You know, or, if Cuba may not be the appropriate destination.

Sandy: Right, right. Well, good answer. I know that the people I’ve been talking to, they’re ready to go—they’re running, they’ve got their running shoes on. They might be a little older but, boy, nothing’s slowing these people down (laughs). Oh Tom, it’s so wonderful to talk to you, thank you so much for sharing Cuba with us! I want to mention again, is your answer. You can go there, and really and truly you’re going to learn a lot about Cuba. And really there’s still so much to learn, and of course you can’t really learn it ‘til you get there, and I know you know that. Is there anything else you can think of that we might have left off that you might find interesting to share?

Tom Popper: You know, the number one thing people tell us on our surveys, they say it over the phone, they call us, they just say “Hi, I wanted to call, I want to get some information on travelling to Cuba, I want to get there before it changes forever.” And, it’s so commonplace. We could talk about that, and what that means to people, and you know maybe why, they’re feeling the inclination to go.

Sandy: You know that’s true! They’ve said that to me too. So what do you say to them?

Tom Popper: I say, “Terrific!” Cuba is changing. But you know, you first read a lot of the media, a lot of journalists, everybody wants to get there before a McDonald’s and Starbucks opens up at every corner. You know, will that happen one day? Probably. On every corner? I doubt it, but you know who knows. But, it’s, Cuba does not change that quickly. But, so, what is extraordinary, and I think this is what’s relevant to people, is that we’ve been told Cuba is one way forever. It’s this, it’s forbidden, you can’t go. And, people understand that Cuba has a lot of, a lot to offer culturally, and probably is a fascinating country. And, we all know that once a destination starts to change, it really never goes back. So it’s this romantic notion, of visiting a place that’s special and that hasn’t been developed or overdeveloped. It kind of retains some of its old charm, and I guess, yeah, that’s probably it, and it’s that old charm that people want to see before other influences start to shape what they see and what they experience.

Sandy: Yeah, I think you’re right. The authenticity I guess, you know, and keeping that. Well, hopefully we can watch Cuba change in a way that really does keep that beautiful culture, and I have a feeling we’ll be able to do that. And I want to thank you Tom again for joining us, and we’ll get you on real soon, okay? And keep this conversation going!

Tom Popper: See you in Cuba, Sandy!

Sandy: See you in Cuba! Thank you Tom, take care.

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