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The first impression of a Cuban all-inclusive couldn't have been much worse.

Walking into the open-air lobby of Playa Pesquero, one of the island's newest resorts, I was greeted by a wall decorated with an enormous picture of Fidel Castro and the entire text of a speech he gave in 2005 to open the massive 912-room, nine-restaurant property at the eastern end of the island. It was a long speech.

Great. A week-long exploration of the joys of socialism. I was convinced that our all-inclusive family fantasy was running headlong into the reality of Marxist lectures and all-you-can-drink as long as you drink rum. Which I don't.

This was just not the way our family travelled. We were sun snobs. All-inclusive brought to mind mealtime cattle calls and nights spent listening to tipsy seniors belting out My Way in the karaoke bar.

Previous winter retreats saw us rent villas on St. Lucia, in a fishing village on Mexico's Pacific coast and on Sanibel Island, Fla. Private pool, private beach and plenty of space for mum, dad and two school-age daughters. The logic was: save money, and get more space, by renting places with kitchens. We would have one meal out each day and we would try to make that a special occasion. Otherwise, we would eat in. All well and good until you actually have to stock the shelves of a vacation home. Or try to find a fine dining experience on Florida's Gulf Coast.

We lost at least half a day foraging for food in each of our week-long getaways. Buying a bunch of fresh-picked bananas in a St. Lucian market is charming. Buying $200 worth of staples such as cooking oil, mayonnaise and dried pasta in a Caribbean supermarket is aggravating. Half the food gets left behind at week's end.

The other downside of making our own meals is that, surprise, someone on vacation actually has to cook. Which means it isn't much of a vacation.

So here we were, standing in Playa Pesquero in the middle of the night with dozens of other families, reading Castro's take on the victory over the Yankee imperialists while waiting for a room. The girls, aged 8 and 9, wanted to run around. This is when things started to look up.

After being assured by a bellhop that the property was safe – all the staff spoke English – we turned them loose. They don't walk to school alone in Toronto, but the lobby was full of waiters and seemed safe. The kids came back in 15 minutes, giddy. There was a pool on the other side of the lobby. A pool so big they couldn't find its end. And people in the pool were sitting on underwater seats. We had to come see.

I felt better when I saw the bottles behind the swim-up bar. There was rum, in all colours. There was also Scotch. In several single malt flavours. And there was a machine that dispensed pina coladas the way a 7-Eleven store dispenses slushies.

By this point, we had a room and a bellhop in a golf cart to take us there. It was an eye-opening drive past the cigar shop and the 24-hour pasta bar, past the tennis and badminton courts, the shiny-clean children's activity centre with foosball and table tennis, and finally past a fitness facility to an oceanfront suite.

The appeal of an all-inclusive really started to kick in at breakfast the next morning. Okay, it was a buffet. And there was no maple syrup for pancakes. But it was a big buffet, and most of the food was tropical fresh. The girls got a charge out of papaya smoothies and, unexpectedly, sausages. Dad and mum got customized omelettes. The Cubans had cloned a Starbucks outlet next to the buffet, serving first-rate cappuccinos and americanos. This was a treat. We never had decent coffee in our villas.

The true charm of our all-inclusive – located in Holguin province, a seven-hour drive away from Havana, but only 40 minutes from a large regional airport – took longer to comprehend. It sank in when the kids jumped into a water polo match, while mum and dad reclined poolside, reading books. I realized we were truly carefree. (Actually, my wife pointed it out.) The kids were free to wander – guards surrounded the fenced property – and there was an endless variety of activities. We didn't have to think about our next meal, making the beds or our evening plans. It was all taken care of. We could do as much, or as little, as we pleased.

We had looked at dozens of all-inclusive spots online before settling on Cuba because it was cheap, and Playa Pesquero because our travel agent recommended it. A massive resort that looked impersonal in brochures ended up having the warmth of a friendly small town. Nine restaurants meant nine different food themes. Those who fault Cuban cuisine as bland or flat-out inedible aren't ordering what the boats bring ashore – the fresh lobster, calamari and swordfish steaks were outstanding.

Luis, the bartender at the swim-up bar, became my new best friend as he described life in Cuba's baseball leagues and his dream of making the Blue Jays. The kids fell in love with our breakfast waitress, who fussed with their hair.

The range of free activities at this resort would challenge even the most active of families. We did give up a bit of the sense of discovery that comes with exploring on a vacation. But it's hard to beat walking out the door onto a white-sand beach, where kayaks were stacked next to paddle-boats and catamarans. There was a beachside shack filled with snorkelling gear. I never saw anyone wait for a water toy.

My wife was horrified to see lessons offered in archery and shooting, with seriously powerful bows and air rifles. When she wasn't looking, the kids and I became crack shots.

There were bikes for trips off property, and scooters too, for those who put little value on going home with all four limbs attached. Cuba's pothole-filled roads are not up to the standards of Cuba's resorts.

Those willing to pay for extras could fly to Havana – $700 a person – or take day-long bus tours of revolutionary sites, along with a cigar factory, for $200. We chose an afternoon outing to swim with dolphins at a marine sanctuary, which was magical, and offered a brief glimpse of a lush but impoverished rural countryside.

It helped that we picked a resort suited to our needs. Playa Pesquero and the other slightly smaller and cheaper resorts in eastern Cuba's Holguin province focus on families. You can find karaoke, even bikini contests, but you have to look for these adult activities, and the action slows after 10 p.m.

For those without kids, the strip of Cuban all-inclusives near Varadero and Havana cater to singles, and the dance floor doesn't empty until dawn. For those who have never been to Cuba, be ready for the fact that there's limited Internet access – I think being BlackBerry-free is a blessing.

I came home from Cuba an all-inclusive convert. Budget-wise, the two different approaches are a wash: Both cost our family about $1,000 a day. Obviously, it's possible to spend far more on grander all-inclusive properties. If we win a lottery, we're bound for a $5,000-a-night suite in Parrot Cay in the Turks and Caicos or Peter Island in the British Virgin Islands that we noticed while doing online research.

Villas are great as a base for exploring a region. We've rented them in Europe and will do so again. But with six short days to relax and recharge, you can't beat a place that keeps the kids busy and safe, while mum and dad rest an elbow on the swim-up bar. See you soon, Fidel.

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