The Urbanist’s Havana: Talking Points

Yes, You Can Get There From Here
The U.S. has prohibited its citizens from traveling to Cuba since 1961 (not counting a break in the travel ban from 1977 to 1982). Still, over 50,000 Americans—as well as an estimated 300,000 people of Cuban descent, who are permitted to travel freely—make it to the island every year. Here, three ways, both legal and illegal, they dodge the ban.

1. Organized Tour
A bit of paperwork and a big check (trips start at $1,500 per week, without airfare) will land you on a tour run by organizations licensed by the U.S. Treasury to bring groups to Cuba. “I went with Global Exchange, a real turnkey solution,” says Tara Russell, a travel consultant. “It was a comfort to know I was going legally, even if it meant giving up a great deal of independence—and it required a considerably larger budget.”

2. Third-Country Travel
Some Americans leapfrog U.S. restrictions by traveling through Cancún, Toronto, and other international hubs. “I find traveling through a third country straightforward,” says frequent visitor Sam L. “Cheap flights [generally around $400 round trip] to Havana are advertised all over Cancún, making it easy to get to the forbidden island.”

3. Double Passport
“For me, it was super-­simple,” says Guatemalan-American Luis Valenzuela. “I just used my C-4 passport instead of my U.S. one.” It should be noted that dual nationals are under U.S. jurisdiction, making this tactic illegal.

A Note On Getting Back:
Any evidence that you’ve made an illegal trip to Cuba, and you could face both civil penalties and criminal prosecution. “Luckily, Cuba doesn’t stamp passports,” says Mike Johnson, who recently came back from Havana via Cancún. “As far as U.S. officials were concerned, I had been in Mexico.” Still, the world traveler took precautions: “On my last night in Havana, I emptied the contents of my bags and removed anything remotely related to Cuba. I left all receipts, guidebook, business cards, and brochures in the hotel.”

Anatomy of a Shakedown
Habaneros are world-class hustlers, and who can blame them? Still, there are ways to avoid la mecánica, common street tricks designed to snare hard currency.

Photo: Danny Kim/New York Magazine

The Money Hustle: Freelance money changers offer to swap your dollars, but instead of giving you pesos convertibles, which are currently pegged at one to the dollar, they give you the far less valuable (and, for tourists, less useful) pesos cubanos, pegged at 24 to the dollar.
The Sidestep: There’s no financial benefit to dealing with freelancers. Instead, change only at banks and cadecas (exchange bureaus).

The Milk Hustle: Women claiming to be mothers beg you to purchase milk for their babies. More likely, they’ll be reselling it on the black market.
The Sidestep: The government provides six pounds of powdered milk to all children 7 and under, enough to meet most mothers’ monthly needs. Your charitable impulses would be better met by donating to schools or family doctors’ offices.

The Love Hustle: Your new Cuban sweetheart says, “I love you, let’s get married,” but really means, “I like you well enough; when can we emigrate?”
The Sidestep: Before you do something rash like propose marriage, see if your relationship can survive a long-distance cooling-off period. If you just can’t help yourself, at least check out the experiences of other hopeless romantics at

The Stogie Hustle “My friend! Buy some cigars?” is a refrain you’ll hear a dozen times daily in the streets of Habana Vieja and Centro Habana.
The Sidestep:To ensure those black-market stogies are really Cohibas and not one-peso cheroots with a fake band, buy your smokes in one of the many Casas del Habano around town.

The New Normal
In April, the Cuban government adopted a passel of economic reforms—some popular, some less so—that amount to revolutionary Cuba’s most ambitious capitalist experiment to date. Here, the three most sweeping changes.

Over 180 professions, including cobbler, street vendor, and barber, are now permitted to work for themselves, instead of being employed solely by the state.
Impact on locals: “You can buy anything on the street these days,” says driver and cook Daniel Sánchez. “Last week, a guy passed my house selling piggy banks and bifocals.” Of course, private enterprises charge more than state-run ones, so only those with the means can take full advantage.
Impact on tourists: Some 330,000 Cubans around the country have entered the private sector under the new regulations, which means more taxis, more private restaurants, more rooms for rent, and street food everywhere.

The government relaxed laws for renting private homes and running private restaurants.
Impact on locals: Cubans can now contract labor, rent more rooms to tourists (including entire independent homes—previously illegal), and seat up to 50 people in private restaurants (up from twelve under the old law).
Impact on tourists: Increased competition gives visitors more leverage in bargaining for room rates, and the opportunity to rent an entire house or apartment.

A reduction in food rations to all but the most vulnerable, including children and pregnant women.
Impact on locals: Says mother of three Yanina Domínguez: “Our salt ration has been cut to a little sack every three months. If that doesn’t last, we have to buy it in the dollar stores. It’s not easy.”
Impact on tourists: As rations diminish, it could lead to higher prices for prepared food and, sadly, more begging in the streets.

Castro’s Children

In his new book, Habana Libre (Damiani), New York photographer Michael Dweck captures young middle- and upper-class Habaneros (as well as the middle-aged sons of Fidel Castro and Che Guevara) reveling in their city of dance halls, beach clubs, drag strips, and grand movie palaces.

The Urbanist’s Havana: Talking Points