Commentary: I’m kind of bummed about Obama’s Cuba trip. But not for the reason you think.

A couple alight on a tourist bus in Havana, Cuba, Cuba on Feb. 18, 2016.

A couple alight on a tourist bus in Havana, Cuba, Cuba on Feb. 18, 2016.


President Obama isn’t scheduled to land in Cuba until March 21, but I’m already getting wistful over the red tape that’s likely to be cut. The truth is, I love the idea behind some of that red tape, and it has nothing to do with Che Guevara, cigars or cars with tail fins.

Since the Clinton Administration loosened limits on travel to the island, legions of Americans headed to Cuba have been subject to a “people-to-people” requirement that visitors can‘t just flop on the beach, groove on music, hoard cigars and drink rum.

Under the requirements, Americans are supposed to make sustained and repeated social contact – to spend face time with rank-and-file Cubans -- not just government officials and bartenders.


As a result, thousands of travelers have been talking to thousands of teachers, students, artists, performers, athletes and workaday families. It isn’t a perfect program—in fact it can be maddeningly vague. (Some details.)

But our leaders’ idea was that, in an open conversation, American values would shine through and the unworthiness of Cuba’s regime would be made clear.

And here’s a nice twist: Cuba’s leaders liked the idea, too, because they figured an open conversation would reveal Cuban values and the silliness of American propaganda.

Anyway, rank-and-file Americans and Cubans have been talking to each other in ever-greater numbers, which, from where I sit, can only be good. Because some Americans aren’t all that good at talking to strangers.

Until they land on one of these itineraries, plenty of American travelers “are not accustomed to visiting kids in a school or going to a community project. Or going into somebody’s home,” said Tom Popper, president of New York-based InsightCuba tours.

Too many American travelers, TV travelogue host and guidebook author Rick Steves said, “just want Lalaland in their travels. They don’t want to get out of their comfort zone.”

But so often, the greatest rewards lie just beyond the reach of your comfort zone (and your selfie stick). And once abroad, people typically find they have more in common than their governments want to admit.

Many Europeans learn this quickly because they live so close together. The idea comes more slowly to many Americans, because most of us have never left this country. (Of about 322 million Americans, only about 126 million have passports.)

So at the moment, to quality for a general license from the Department of the Treasury – that is, to visit Cuba without any special paperwork – your trip needs to fit into one of 12 approved categories, including family visits, professional exchanges, religious activities, philanthropy, sports competitions, etc. People-to-people educational activities is one of them.

But the president will visit March 21 and 22, which could ease the way for more flights, more cruise ships, more mass tourism, fewer restrictions. And come January a new president will push a new Cuba policy.

Where our Cuba posture gets more friendly or less friendly, there’s a good chance the Cuban people-to-people program will go away. And that has me a little sad. And thinking about the rest of the world.

What if we travelers left governments out of this and made person-to-person contact a higher priority on all our trips? What if we borrowed a few tactics from folks in the people-to-people business?

As it happens, I have a few right here.

Set a local goal. Then get help. Tour operator InsightCuba’s guides like to send travelers to the farmers market with 5 Cuban convertible pesos (roughly the median weekly Cuban wage) with the assignment of buying all ingredients for a group meal.

“The idea is to see how hard it is to get together the meal,” said InsightCuba’s Popper. Suddenly, conversations with vendors get more detailed, haggling happens, a little money gets spread around, “and they’ll have an interaction that you don’t see at most farmers markets.”

Hire a local guide, preferably without a big bus. Consult the web and guidebooks to find a local guide with good references. These people can build an itinerary around your interests and make introductions.

In Europe, Rick Steves said, he often pays about $100 a day --“a great deal for him [or her] and a great deal for me.”

Make eye contact and start conversations. After all, what’s the point in trying to pass as a local? In the unlikely event that you succeed, nobody will explain anything to you. Take your usual precautions when away from home, but wear your curiosity on your sleeve.

Ask directions, even if you already know them. And allow yourself time for these contacts to grow into larger adventures.

Make ear contact too. Stash those earbuds. Especially if you’re on foot in a city, you’re going to hear telltale sounds. Chase them down (within reason) and you’ll meet artisans working, monks chanting, kids singing, musicians practicing, animals eating – you name it.

Go to church. Or temple. Or mosque. Most religious gathering places are happy to see visitors. Show respect and curiosity and a warm welcome is likely to follow.

Go to college – or a collegiate neighborhood. No matter your age, odds are good you’ll find some people with flexible schedules who want to practice their English.

Do it alone. Or as a group. As InsightCuba’s Popper notes, group trips can ease access; it’s easier for a known organization to book a visit to a school, for instance. But as Steves notes, independent travelers, exploring the world alone or in small, self-directed groups, have the flexibility to embrace serendipity in a way that no larger group can.

Look beyond the usual hotel suspects. At a minimum, personalize the experience by chatting up your hotel’s staff. Better yet, try a B&B or homestay, perhaps through Airbandb or VRBO. On a homestay in a Cuban casa particular early this year, Steves frequently found himself at on the rooftop patio, talking politics with his hosts and other locals.

“If you can go to a bar and meet strangers, that’s wonderful,” Steves said. “But there are all sorts of ways you can have these people-to-people experiences.”

If these kinds of contacts boosted profits for cruise companies, hoteliers and the people who run casinos and theme parks, the travel industry would do more to make them happen. But they don’t.

If it’s not really our government’s job to make us into citizen diplomats, this stuff is up to us.

Twitter: @mrcsreynolds