Kuba

In his song 'Cienfuegos,' Benny Moré described his home city as the city he liked best. He wasn't the settlement's only cheerleader. Cuba's so-called 'Pearl of the South' has long seduced travelers from around the island with its elegance, enlightened French airs and feisty Caribbean spirit. If Cuba has a Paris, this is most definitely it.

Leap-frogged by almost all international visitors, Cuba’s two smallest provinces, created by dividing Havana Province in half in 2010, are the preserve of more everyday concerns – like growing half of the crops that feed the nation, for example. But in among the patchwork of citrus and pineapple fields lie a smattering of small towns that will satisfy the curious and the brave.

Most travelers say hello and goodbye to Las Tunas Province in the time that it takes to drive across it on the Carretera Central – one hour on a good day. But, hang on a second! With laid-back, leather-skinned cowboys and poetic country singers, the province is known for daredevil rodeos and Saturday-night street parties. Here barnstorming entertainment is served up at the drop of a sombrero.

Havana's Old Town – the site where the city first took root in 1519 – is one of the historical highlights of Latin America, an architectural masterpiece where fastidiously preserved squares and grandiose palaces sit alongside a living, breathing urban community still emerging from the economic chaos of the 1990s. The overall result is by turns grand and gritty, inspiring and frustrating, commendable and lamentable. No one should leave Cuba without seeing it.

Habana del Este is home to Playas del Este, a multiflavored if slightly unkempt beach strip situated 18km east of Habana Vieja. While the beaches here are sublime, the accompanying resorts aren't exactly luxurious. Rather, Playas del Este has a timeworn and slightly abandoned air, and aspiring beach loungers might find the ugly Soviet-style hotel piles more than a little incongruous. But for those who dislike modern tourist development or are keen to see how Cubans get out and enjoy themselves, Playas del Este is a breath of fresh air.

The pioneering ecovillage of Las Terrazas dates back to a reforestation project in 1968. Today it’s a Unesco Biosphere Reserve, a burgeoning activity center (with a canopy tour) and the site of the earliest coffee plantations in Cuba. Not surprisingly, it attracts day-trippers from Havana by the busload.

Neither Occidente nor Oriente, Camagüey is Cuba's provincial contrarian, a region that likes to go its own way in political and cultural matters – and usually does – defying expectations in Havana and Santiago. These seeds were sown in the colonial era, when Camagüey's preference for cattle ranching over sugarcane meant less reliance on slave labor and more enthusiasm to eliminate the whole system.

A historic refuge from the law for everyone from 16th-century pirates to 20th-century gangsters, La Isla is perhaps the quirkiest castaway destination you ever will see. Dumped like a crumpled apostrophe 100km off mainland Cuba, this pine-tree-clad island is the Caribbean's sixth-largest. But the Cayman Islands this isn't. Other tourists? Uh-uh. And if you thought mainland Cuba's towns were time-warped, try blowing the dust off island capital Nueva Gerona, where the main street doubles as a baseball diamond, and the food ‘scene’ is stuck in the Special Period. Yet, if you make it here, you're in for a true adventure. The main lure is diving some of the Caribbean's most pristine reefs, but otherwise get used to being becalmed with the coral, the odd crocodile and a colorful history that reads like an excerpt from Treasure Island.

On first impressions, Havana can seem like a confusing jigsaw puzzle, but work out how to put the pieces together and a beautiful picture emerges.

Elegant and old, this relatively hush city spells oasis to the traveler weary of confrontation. Predating both Havana and Santiago, it has been cast for time immemorial as the city that kick-started Cuban independence. Yet self-important it isn't. The ciudad de los coches (city of horsecarts) is an easygoing, slow-paced, trapped-in-time place, where you're more likely to be quoted literature than sold trinkets. Cuba's balmiest provincial capital, it resounds to the clip-clop of hooves; nearly half the population use horses for daily travel.