A street scene in Trinidad, Cuba.
(Photo courtesy Alexandra Sicotte-Levesque)

Every winter, throngs of Canadians shed their parkas and mittens for the warm weather of the Caribbean. Their number one island destination: Cuba. It’s the third most popular tourist destination for Canadians after the U.S. and Mexico. And 40 percent of all visitors to Cuba are Canadians – to the tune of one million every year.

Despite the United States’ frosty history with Cuba, Canada has maintained its relationship with the largest island in the Caribbean since the 18th century. Along with Mexico, Canada was the only other country in the Western hemisphere to continue diplomatic relations with Cuba in the years after Fidel Castro took power in 1959.

It’s a cultivated economic relationship – glossy advertisements paid for by the Cuban government are everywhere in Canada. Tourism is Cuba’s largest industry and Canadians are its biggest purveyors. Every all-inclusive Canadian travel Web site has an entire section on Cuba, extolling the virtues of big beach cities like Varadero and Holguin. And direct flights to the island leave from all the major east coast Canadian cities every day.

When Jason Pawlett, a writer from Toronto, went on vacation to Cuba in February, he was greeted by signs in English, Spanish and Russian at the Varadero Airport. Lured by the cheap cost – it was $1,100 Canadian (about $950 U.S.) including taxes for an all-inclusive one week vacation that covered flight, hotel, food and drink – he spent the week on the beach, deciding not to venture off of his resort property.

“The people are so fantastic and it’s super safe for tourists, because tourism is so important to them.” He says the accommodations were modest, clean and a little worn, like stepping back in time. There were chickens and a rooster just outside of his luxury four star resort room.

Canadian Jason Pawlett in mid-flight with his skydiving instructor over the beach in Varadero, Cuba.
(Photo courtesy Jason Pawlett)

Christopher Stewart, a lawyer in Newark who grew up just outside Toronto, traveled to Cuba three times as a teenager on trips for high level soccer teams in the 1990s.

“All of my experiences were really positive aside from the fact that Cuba was in a time warp,” he says. “It was obvious that the society was at least 30 years behind what we had in Toronto.”

“It never seemed like anyone was unhappy…but at the end of the trip, we gave the Cuban players extra parts of our uniforms. Practice shorts and Adidas shirts that we could spare,” he says. “And you could tell they needed it.”

Alexandra Sicotte-Levesque is a filmmaker living in New York City who grew up in Montreal. She traveled to Cuba in the early 1990s, just after the fall of the Soviet Union and then again for New Year’s in 2012. She says the contrast was startling.

Canadian Alexandra Sicotte-Levesque and her friends on vacation in Havana, Cuba.
(Photo courtesy Alexandra Sicotte-Levesque)

“When I was there the first time, people didn’t really leave their hotels and there were stray dogs everywhere. But when I went back a few years ago, it was very different,” she says. “You think you’re in Spain, it’s gorgeous.”

But she was keenly aware of the disparity between tourists and locals. “We rented a car to tour around the island, but no one was on the roads because no one can afford a car,” she says. “And the Cuban friends we made were not allowed into the resorts.”

Now that the U.S. is on the cusp of restoring its diplomatic relations with Cuba, Sicotte-Levesque thinks the island is about to change again: “Everything there seemed to stop in the 1960s, so it’s very special,” she says. “I was thinking we better get back before McDonald’s comes in.”