Kuba

In any other country, this attractive colonial city would be a cultural tour de force. But cocooned inside illustrious Sancti Spíritus Province, second fiddle to Trinidad, visitors barely give it a glance. For many therein lies the attraction. Sancti Spíritus is Trinidad without the touts. You can dine, listen to boleros on the plaza or search for a casa particular without hassle.

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.

Matanzas is like a sunken galleon left at the bottom of the ocean. Most casual visitors to Cuba sail right over the top of it (usually on a tour bus to Varadero), but, a few curious adventurers dive down and discover that this ostensibly scruffy city is still full of priceless treasure. Go back a few generations and Matanzas was a very different place. During the 18th and 19th centuries, the city developed a gigantic literary and musical heritage, and was regularly touted as the ‘Athens of Cuba.' Two pivotal Cuban musical forms, danzón and rumba, were hatched here, along with various religions of African origin. Matanzas also hosts one of Cuba’s finest theaters, and was the birthplace of some of its most eloquent poets and writers. Despite the contemporary aura of decay, the cultural riches haven’t disappeared. You just need patience, imagination and a Sherlock Holmes hat to disentangle them.

Varadero, located on the sinuous 20km-long Hicacos Peninsula, stands at the vanguard of Cuba’s most important industry – tourism. As the largest resort in the Caribbean, it guards a huge, unsubtle and constantly evolving stash of hotels (over 60), shops, water activities and poolside entertainment; though its trump card is its beach, an uninterrupted 20km stretch of blond sand that is undoubtedly one of the Caribbean's best. But, while this large, tourist-friendly mega-resort may be essential to the Cuban economy, it offers little in the way of unique Cuban experiences.

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.

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.

Diminutive Ciego de Ávila's finger-in-the-dyke moment came during the late-19th-century Cuban Wars of Independence: it became the site of an impressive fortified wall, the Trocha, built to keep out rebellious eastern armies from the prosperous west. Today, the province continues to be the cultural divide between Cuba's Oriente and Occidente. Most tourists come here for the ambitious post–Special Period resort development of Cayo Coco and Cayo Guillermo. The brilliant tropical pearls that once seduced Ernest Hemingway have had their glorious beaches spruced up and daubed with over a dozen exclusive resorts.

Few parts of the world get named after yachts, which helps explain why in Granma (christened for the boat that delivered Fidel Castro and his bedraggled revolutionaries ashore to kick-start a guerrilla war in 1956) Cuba's viva la Revolución spirit burns most fiercely. This is the land where José Martí died and where Granma native Carlos Manuel de Céspedes freed his slaves and formally declared Cuban independence for the first time in 1868.

Cuba's third-largest city is easily the suavest and most sophisticated after Havana. The arts shine bright here and it's also the bastion of the Catholic Church on the island. Well known for going their own way in times of crisis, its resilient citizens are called agramontinos by other Cubans, after local First War of Independence hero Ignacio Agramonte, coauthor of the Guáimaro constitution and courageous leader of Cuba's finest cavalry brigade.