When the thermometer drops and the snow flies, when the doors of the car are iced shut and the dog sniffs the air, shivers, and refuses his morning walk, the migration begins. For tens of thousands of Canadians the mid-winter sunspot vacation is an annual rite, less a luxury than a necessity; a brief, blissful reprieve from dark days and windswept nights.

But where, exactly, to go? And how to ensure you get the most out of your time in the sun? The options are legion: a hundred-plus inhabited islands (along with Mexico) winking like emeralds in a tropical sea. Each of these islands boasts its own unique culture, together with a range of resorts, accommodations, attractions and price points. Faced with this bounty, deciding where best to thaw one’s frozen toes can be daunting. Yet for most of us it comes down to a few favourite spots.

The big four

Together, Cuba, the Dominican Republic, Mexico and Jamaica soak up the vast bulk of traffic to the Caribbean—and for good reason. “The larger islands are going to be the cheapest. They have well-developed tourist industries and infrastructure, and there’s lots of competition between resorts and lots of flights in and out,” says Sarah Greaves-Gabbadon, deputy editor of Caribbean Travel + Life magazine. “Small islands like Anguilla and Provo, where there are more villas than resorts, are not going to be cheap. They can’t compete on cost, so they cater to a more up-scale clientele.”

Understandable, then, that cost-conscious travellers looking to vacation in the sun flock en masse to the Caribbean’s four populous land masses. At these four destinations, in particular, the all-inclusive resort is king, rolling flights, ground transportation, lodging, meals, and drinks into an affordable, easy-to-book package.

What you want

While a resort in the Dominican might bear a striking resemblance to a resort in Cozumel, Mexico, the destinations and what they have to offer are not interchangeable. “It depends on what’s important to you,” says Janice MacIsaac, who vacations in the Caribbean for pleasure, and also books conventions there for the Canadian Association of Emergency Physicians. “The Dominican is famous for its beautiful beaches, but the food in Mexico is a little nicer.”

To further complicate matters, there are significant regional differences within countries: Cancun, Mexico, is a notorious party spot, whereas further south along the Mayan Riviera the resorts are quieter and more family oriented. Likewise, tourists in Veradero, Cuba, can take advantage of day-trips into Havana, while those booking into more remote Cayo Coco are effectively resort-bound.

Before you even start shopping for an all-inclusive, suggests MacIsaac, make a wish list of what you absolutely must have, and what you’re willing to compromise on. “You might not be willing to bend on a great beach or nightlife, but you might not care as much about wind surfing or golf courses.”