Home Articles The “How, Where, When and Why” of Traveling to Cuba

The “How, Where, When and Why” of Traveling to Cuba

Welcome to Cuba, a country of rich heritage, fine beaches and bewitching, weathered city centers.

For the past half-century or so, American travelers have maintained a complicated relationship with this island country, having been locked out in the Cold War and ensuing decades. But travel restrictions started to loosen around the turn of the new century, and in 2009 then-president Obama signed a bill into law that eased the historical travel restrictions. Cuba became (more or less) fair game for American travelers.

Still, some Americans remain wary of traveling in Cuba. They really shouldn’t be, though – just ask Canadians. For decades, traveling Canadians, whose country harbored none of the same strained relations as the States, have enjoyed the riches and adventures of Cuba. As long as you obtain a Cuban general travel license and fly to the right airport, you’ll be more than fine!

To help answer some of the burning questions you might have surrounding travel to Cuba, here are the “how, where, when and why” of traveling to Cuba.

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Most international travelers are free to come and go in Cuba without much administrative hassle. Americans, however, have one small hoop to jump through: the general license, or Cuban travel card. To obtain a general license, you need to prove that you’re traveling to Cuba under one of the 12 permitted categories of travel, the most popular of which, for travelers, is citing “support for the Cuban people”. It’s a relatively quick and painless process, but it’s necessary.

As far as booking a trip to Cuba, the best way to go is through Travelzoo’s last-minute deals or travel packages. Travelzoo curates perfectly priced travel deals, sifting through available flights and accommodation and vetting them to present the absolute best. If a trip to Cuba is in the cards, check out Travelzoo.com/ca/collection/last-minute to get an irresistible deal.


There are numerous points of interest in the large island country, but the two main hotspots are the capital city of Havana and the popular beach resort destination Veradero.

The former is a bustling city, with colorful colonial architecture, plenty of cool, old American cars driving around, and cigar vendors aplenty. Catch some live music in one of the city’s many lively bars, chat baseball with a local, or sip some of the country’s world-famous rum.

In Veradero, an all-inclusive is the way to go. Book an all-inclusive vacation to Veradero through Travelzoo and simply relax on the beach for a week, soaking in the bright Caribbean sun.


Cuba remains sunny more or less year-round. Still, precipitation may factor into your decision on when to visit, as the wet season (from May to September) experiences an uptick in heavy downpours. For that reason, the dry season, lasting from March to April is probably the best – and certainly the most popular – time to visit Cuba.


Finally, you may want to know: why should you visit Cuba. Spend even an hour in this country, and you’ll have your answer. It is a boisterous, beautiful and adventure-packed country, blessed with kind people and mesmerizing scenery.

One trip to Cuba, and you’ll be mambo-ing back there for more!