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A flight to Cuba, before they fly away Add to ...

Viva Cuba! I pass the billboard every morning as I drive to work in dreary downtown Toronto. The clear water, white sand and fabulous couple who appear to adore vacationing together are irresistible. Why shouldn't our family of five go?

It will be our first winter vacation, and the kids, if things go according to plan, won't be living with us indefinitely. They are 21, 19 and 16, and we can go days without being in the house at the same time. I worry that once they find significant others, whom I may or may not care for, we'll never vacation as a family again. So what if I'm blowing a year's university tuition? Everyone knows you're not supposed to put a price on precious memories.

I do no research whatsoever. Cuba looks terrific on the billboard and the departure taxes are less than for the other destinations. A friend has recommended the Breezes Jibacoa. It's all-inclusive and has a beach, so I book it. Just one week without a care in the world – that's all I ask for.

Departure day comes, and I take my life in my hands and wake them at 2:30 a.m. to make a 10:30 flight. It isn't pretty.

By the time we reach Varadero, we've about had it with lineups and each other. We've recovered two of three bags off the conveyor belt when we realize the unthinkable has happened: Our 19-year-old son's bag has vanished, along with enough sundry items to stock the island for a year. We fill out a report and board the bus to the resort, where we're greeted by a cold driving rain and high winds. I notice that the front desk staff is wearing scarves and gloves. It's the coldest it has been in Cuba in 30 years and the seven-day forecast posted in the lobby is a heartbreaker: cold, rainy and windy, with the faintest hope of sun on Friday, which is six days away.

The mood is ugly as we line up for the lunch buffet. I stand staring blankly at the anemic vegetables, and a cold stream of water runs down my neck and back from an overhead leak.

Back at the table, Rachel, 21, wants to know why the average age of the hotel guests is 45. I start to panic. I deep-six my standard lecture on the horrors of alcohol and encourage them to do whatever it takes to keep us from killing each other over the next week. By 11 p.m., they're fist-pumping up a storm at the disco and drinking like fish. I can barely contain the urge to lecture them about cirrhosis of the liver, but I come to my senses and keep my mouth shut.

The next morning, I find them lying in bed in the dark, watching a movie on HBO. Their rooms have been transformed into bat caves. If Jonathan had his headset on for Call of Duty, I'd swear we were at home. I take the bull by the horns and tell them we're going for a hike up the monstrous hill behind us the next day, come hell or high water.

Two out of three show up, which isn't bad. Our guide is a handsome young man in his 20s. When we reach the lookout at the top, he points me in the direction of Florida. I ask if he has ever been off the island and he tells me he applied to travel to Canada once, but suspects he was denied because he speaks English and had no wife or kids to come back to. I become indignant on his behalf. On the walk back, we pass through the ramshackle property of a local farmer and talk about what it would be like to never see anywhere else in the world except where you were born. As the week progresses, I notice our family conversations are becoming less about crappy weather and more about socialism. I seize the moment and hire a driver to take us into Havana.

We're at the driver's mercy when it comes to where to go.

The kids are nonplussed by Castillo San Salvador de la Punta, a crumbling Spanish fort dating to 1589, but the vintage cars puttering through the city are a huge hit. They note the absence of advertising, heavy traffic and noise, and notice that the tattered public buses for Cubans are much different from those for tourists. We talk over lunch about the skinny stray dogs on the street, the shocking disrepair of the city and how it still manages to be beautiful. The food is horrific, but we tip generously. We wander through a flea market filled with vendors hawking useless wares, but the kids buy a few things anyway because it feels good to give someone a sale.

With little time left, I ask the driver to take us to a synagogue in old Havana I had heard about. “You want to go to Israel?” the driver asks. I nod enthusiastically. I hear it's warm there.

One of only three synagogues still active in Havana, Temple Adath Israel isn't much from the outside, but inside it's a small miracle. The Jewish population of the city peaked at about 15,000 before the revolution and more than 90 per cent left the country afterward. With only 120 families as members, the synagogue remains Orthodox, holds daily services, operates its own pharmacy and runs a religious school. I'm struck by how, against all odds, this tiny Jewish community continues to thrive when assimilating would be so much easier. I look at my kids and hope something takes hold.

And then on Friday, our last day, the sun comes out. We're elated to see it, but the truth is we've had a pretty good week without it – not the one we expected, but good nonetheless. By the time we leave, Jonathan has given his only sweatshirt to a security guard who was shivering on the overnight shift. The girls make sure that everyone from the waiters to the house maids are tipped generously (with my money) and leave most of their sundry items and a few pieces of clothing behind in the room. We take one last look for the stray cats we have been feeding all week and give them one last snack.

I look at my family and feel proud. The tans are nothing to speak of, the suitcase never showed up, but we're heading home with so much more than we brought. The sun shines in many different ways.

* * *

Getting there
Air Canada flies to Varadero non-stop from Toronto and Montreal.

Where to stay SuperClub Breezes Jibacoa 53 (47) 295-122; www.superclubscuba.com/brand_breezes/resort_jib/. From $170. On Arroyo Bermejo Beach on Cuba’s north coast, midway between Havana and Varadero. Minimum age 14.

What to do Temple Adath Israel Acosta 357, Havana; 53 (7) 861 3495; www.adathcuba.org/index.html.

S.A.

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