Friendly Planet recently acquired Insight Cuba. Recommend reached out to both Peggy Goldman, founder and president of Friendly Planet and Tom Popper, president of Insight Cuba to discuss the acquisition, what this means for bookings to Cuba, and what the duo thinks of the current travel restrictions to the island. During our excited conversation, we discussed how you, the travel advisor, can better sell travel to Cuba, and what they’re seeing as the current climate when it comes to travel to the island. So, sit back, and let’s talk Cuba.

Michelle Marie Arean (MMA): Can you tell us a little bit about why Friendly Planet decided to acquire Insight Cuba?

Peggy Goldman (PG): We saw a good opportunity. It was an opportunity that came to us unexpectedly we had no thoughts about acquiring anything. When the opportunity presented itself Ilan [Ilan Fink, president Friendly Planet and Peggy’s husband] looked at me and said “What, are you nuts? I want to retire.” And we started thinking about it, and talking about it, and we realized this was an opportunity for us that we couldn’t pass up.

Insight Cuba is the premier brand for travel to Cuba. And they have been from the beginning. The company that we’ve been watching very carefully since we started to sell travel to Cuba in 2011 when we got our first license; they really set a standard in the industry. Tom and I got to know each other a little bit through the business that we were doing, and It was really an experience to watch them, and see as they set a standard in the industry, and with tom spearheading that effort. I noted it’s not always possible in business to come across an opp that can make you better and stronger in a destination you care about. So when the opportunity presented itself we took it.

Tom Popper (TP): We both have a good read on the Cuba market and the industry. Despite some of the regulatory changes in the trump administration, travel to cuba still remains 100 percent legal for Americans. And it’s actually easier now than it has been just a few short years ago.

With the most recent policy changes, the cruise ship industry had to pull out over night. That’s left a huge vacuum and an opportunity for companies like us who have been operating in Cuba for some time—next year is our 20 anniversary—to handle the pent up demand. In 2020 it’s estimated 1 million U.S. travelers will have traveled to Cuba, so it’s the 2nd largest market for travelers to Cuba. We saw this pairing with the great timing to take advantage of this new era in travel to Cuba.

PG: We are also very compatible in terms on how we market, and to who we market to. Insight Cuba markets and works very closely with the trade. Friendly Planet from it’s conception was a B2C company. We feel together we will be able to grow the volume of travelers going to Cuba and grow it in a responsible and ethical way, and to make sure there is always an opportunity for Americans to travel to Cuba legally and have the best experience.

Salsa dancing in Trinidad, Cuba. (Photo courtesy of Friendly Planet.)

MMA: Will the name Insight Cuba change now that it’s under Friendly Planet?

PG: No! We love the brand. The name will not change. The brand is so strong. Insight Cuba will continue operating under Tom’s direction.

The two brands will continue as twp separate companies. Nothing about Insight Cuba is going to change, and Friendly Planet will continue to do what Friendly Planet does.

MMA: Does this mean there will be changes coming for Insight Cuba? If so, what?

PG: We will have a lot more power to market the destination. And, Hopefully in the future insight Cuba will be able to offer similar opportunities to other parts of the world that we have been offering to Cuba, especially to the trade.

We are still in the organizational stages. But, we will look for opportunities in places we can provide the same kind of experiences that were provided in Cuba. But Cuba of course will be the primary focus, that’s where our hearts are.

MMA: What sets Insight Cuba apart from other tour operators traveling to Cuba?

TP: It is our experience and we, and we use that experience and our relationships to leverage the different experiences we offer to guests. We are a travel company, so we gage our success based in every single experience, every single traveler has with us. Our goal and our job is to just blow them away with emotional experiences, transformative experiences, so they look back and always remember the specific moments during their trip.

Having the access and the connections within the Cuban government and communities across the island, having that access and that trust allows us to share those experiences and those people with our guests, which is remarkable.

We’re not just purchasing a package from a destination management company. We intricately involved with everything we do—every meal they eat, every person they meet, every artist they come encounter with, every musician they have the pleasure of listening to. It makes all the difference in the world, as far as a travel experience and having someone prepare your travel for you. It’s something that’s born from being a traveler myself and spending millions of hours of planning trips for myself.

Being in a country and trying to figure out what do next, what’s going to happen, what town am I going to. And knowing how difficult and daunting it can be when you’re in a foreign country and we take what we’ve experiences in the last 20 years and share it with everybody.

A cigar rolling demo at a farmhouse in Vinales. (Photo courtesy of Friendly Planet.)

PG: That’s a very big deal what Tom is articulating. Cuba is a place where if you can buy a ticket, you can get on an airplane, you can get a visa at airport, you can stay at Air BnB, but if you don’t have the deep connections to the people yoou will be wandering around and you’re not having the experience you could have in Cuba. It really is about the relationships, and we learned that when we started in 2011 we had to scramble to get those kids of connections and it took us a while. Insight Cuba has more than 10 years ahead of us, and I can tell you from experiences that’ the thing that makes it most different. Today Insight Cuba is the most established brand in Cuba. It makes all the difference.

MMA: Cuba was booming a couple year ago when it opened for travel by Americans, have you seen any changes in the amount of travelers or interest since then? Has it decreased at all?

TP: Every time you have a policy announcement you have an ebb and a flow. After then June 5 announcement, the headlines were Cruise ships pull out of Cuba… other than the cruise ships being pulled out. Of Cuba, travel remained legal. So you had confusion in the marketplace, which is commonplace for Cuba. Because what other destination is there where there are travel regulations where you have to comply with the government.

After the confusion, the market starts to rebound and people start to become re-aware of travel to Cuba. After June announcement, which happened in the beginning of the off-peak season, and now we are starting in the recovery mode as we enter peak booking season. We are looking forward to a return to 2018 numbers and even bigger.

The way to look at it is almost as a new era of travel has begun. Certainly when the 2016 elections happened there were some concerns about legal travel to Cuba, because it’s usually associated if the Democrats are in the White House there’s going to be more travel to Cuba, if a Republican is in the White House there’s going to be less travel to Cuba. That’s been brought on over history, what’s amazing is that despite all the negative attention with regards to the Trump administration and the Republican administration, it is still legal. We are in this new era where legal travel to Cuba is here to stay. It is a thing. That’s an important message to get to the traveling public because they continuously get confused.

PG: It is shocking that the cruises decided to pull Havana from their itinerary pretty abruptly. I think that was was a big shock. That was a headline in addition to the news of the changes and regulations. Just like anything, people don’t read the details. They read the headlines, and there’s a big confusion.

The real message doesn’t get down to the traveling public or trade in a proper way. The more of that that we are able to spread the word that Cuba is legal and it’s open for business and it’s easy to go, the better it will be.

We are noticing in our metrics, we are seeing that there’s a lot of interest by the way people are behaving on our website. Just in August usually people go to sleep, but we saw a huge spike in number of searches for information on Cuba on our website site, and the amount of time people were staying on the Cuba pages were longer.

The interesting thing to note about cruises is in the last year there were about 900,000 people who either signed up for or hadn’t actually taken cruises who had Cuba on its itinerary which is spectacular. Because people booked the cruises specifically because they liked the cruise, but they booked that cruise because they were going to be able call on Cuba. That is proof that there is a tremendous interest. People cancelled their trips because Cuba was taken off their itinerary. A lot of those people ended up contacting us, and Insight Cuba as well, to find out if they could still go. Unfortunately not all 900,000 wanted to travel with us, but that’s a clear indication of the interest that exists.

Views of Vinales Valley. (Photo courtesy of Friendly Planet.)

MMA: How can travel advisors learn more about your trips to Cuba and how to navigate the travel restrictions?

TP: We hold a monthly Cuba Chat for travel advisors where they can ask the expert and we usually have a topic of discussion that we talk about for 10-15 minutes, and then we open the floor. It’s a very free flowing conversation and we have 20-50 agents.

It’s become hugely popular with travel agents because they ask questions and it spurs other questions from other agents and it’s a collective understanding of what’s going on…what hotels can they book, tell us about private homes, can I tell my clients about any doubts, what airline s are traveling to Cuba, can you make it happen without me going through a lot of trouble.

MMA: Where can travel advisors find out more about these Cuba Chats?

TP: They can write to and we’ll put them on our invitation list. And they can also request brochure at the head of our website and fill out the form and there’s a check for agents and you’ll be automatically put on list and they’ll be emailed when there’s one happening.

PG: Hopefully we’ll be able to reach the trade in other ways as well. We are intending to reach the members of the trade in different ways in an aggressive way to get them the information that they need to answer their client’s requests when they get a call. Agents are in a lot of ways introducing Cuba as a destination to their clients and they’ll be able to do it with confidence and eagerly.

Agents have a lot on their plates and they need to be able to handle destinations like Cuba that are difficult to plan if they don’t’ have the knowledge or the contacts to be able to do it easily with a phone call. We are working on lots of plans to be able to present to agents.

PG: We don’t have dates, but we are looking into FAMs. Any agents interested can go to Insight Cuba site and send a message letting us know and we’ll be put on a mailing list so once plans are completed we can reach out.

For more information, visit or For a Cuba FAM opportunity in October, click here.