Dan's a dentist from Chicago with a penchant for diving and a special place in his heart for Donald Trump.
"You know what's great about Donald?" asked Dan as we chatted between dives at Bahía de Cochinos.
"The great thing about Donald," Dan went on, "is that he's not beholden to anyone."
"I see," I said, wishing I could share Dan's comfort in the notion.
"And he'd get this place opened up a whole lot faster too," he continued. "It's happening though. I tried to come a few years ago and it was impossible, this year no problem. It's gonna get crowded!"
Cuba's inevitable fate as a free-market-fuelled American vacation haven is a widely accepted wisdom. Bring up Cuba in conversation, and it won't be long before you hear something like: "I'd love to go, and I'd better get there soon, y'know, to see it... before the Yanks take over."
On the north coast, about 90 kilometres east of Havana, lies Varadero, an insular kitsch-fest of package getaways and all-inclusive, beachfront retreats. It's a place of bright plastic bracelets and open-top bus tours, where Che Guevara T-Shirts, towels and mugs can be bought three for two with no sense of irony required, where you can have Heinz on your hamburger and ice in your Coke, where Cuba provides the climate, and the mojitos, and little else.
Places like Varadero have their function, of course — it's good for kids and retirees alike. But some dread that Varadero is the blueprint for the coming Cuba — that political concessions will quickly turn the entire Cuban archipelago into an orgy of capitalistic tack, like a giant Key Largo or Disneyland in Spanish.
Travelling around the rest of the country, though, makes this impending plutocratic dystopia difficult to foresee.
Three hundred kilometres west, in Viñales, the streets are packed with international accents. They barter for hats, postcards, carvings and sandals at roadside gift stalls and order cocktails and tapas at suave new bars that under old laws wouldn't exist at all. Signs, surely, that Cuba is the next Cancún.
Just a few hundred metres out of town though, is a Cuba that hasn't changed for centuries. Amongst giant limestone mogotes, men and oxen till fields, coffee is grown, roasted and ground by hand, tobacco is rolled on wood into thick cigars, the roofs are thatched, and transport is by horse and cart.
In town, salsa rings from the town hall out into the square where old men drink from flasks of rum behind huge curtains of cigar smoke next to chicas in tank tops tapping out texts on cellphones that until recently were an illegal commodity.
Viñales is a tourism destination no doubt, and the smell of money and progress is in the air, but it is far from overrun, low on cheap novelty, rich in heritage, and adapting gracefully to an increasing influx of visitors and new freedoms of private enterprise.
Cuba's heart, of course, is in Havana, and it beats hardest in Habana Vieja — Old Havana. I'd arrived in the old quarter after 27 hours of delayed flights, missed buses, awful heat and bungled communications. Hot, thirsty, beaten, and still dressed for winter in Toronto, I was willing to follow whoever could show me a bed and an air conditioner.
His name was José, and 20 minutes later he'd found me a room, after an hour I was buying him beers at the bar, and the next day I was on the back of his bicycle taxi for a tour of the capital.
José knew opportunity when he saw it.
"Es beautiful, sí!?" José said, often, as he pedalled us around the city, past the giant dome of the Capitolio, from where the country was governed prior to revolution, past the birthplace of José Martí, a national hero who warned of the threat of American expansionism as far back as 1891, and past the Museo de la Revolución, formerly the palatial residence of a dynasty of crooked Cuban presidents and now a brimming gallery of revolutionary artifacts.
"Es beautiful, sí!?" José said, again.
It is. Both the Museo and the Capitolio are immense and intimidating structures, impeccably maintained, and a far cry from the cracked stairwells, failing balconies and cavernous potholes that gnaw at the rest of Havana.
I asked José if things were improving for people since Raúl Castro took over for his brother Fidel in 2008.
"Under Raúl," he said, rocking his hand in a so-so gesture. "It's better, un poco, a bit."
There are changes in Cuba certainly. People can now buy and sell their own cars and homes, and own their own computers and phones. But such meagre allowances are more akin to the slow letting of responsibilities by a parent to a teenager than the full-flung self-determination Cubans yearn.
"I love my country," one man told me. "But it is really just a big prison."
These sentiments run wide and deep, eight years after Raúl took over. He states his position thus: "I was not chosen to be president to restore capitalism to Cuba. I was elected to defend, maintain and continue to perfect socialism, not destroy it."
Stateside, Obama seems keen to normalize relations, but must contend with an obstinate Congress. American businesses, meanwhile, are reluctant to invest in a state that has never been shy to seize American assets. Where once there was cold war, now there are cold feet.
Barack and Raúl may be the first respective leaders to talk to each other since 1959, but any change in Cuba will be more incremental than immediate, more restrained than radical.
But maybe not. Perhaps a sweeping transformation is at hand. To find out, I’d have to come back in five years or so, possibly during President Trump’s second term.
"Bring it on," says Dan, donning his tank and flippers, ready for another dive in the Bay of Pigs, where in 1961 Cuba so soundly drubbed a more hurried, brazen, and utterly failed American invasion. "I say bring it on."