Kuba

Sorry Havana. Santa Clara is Cuba's most revolutionary city – and not just because of its historical obsession with Argentine doctor turned guerrillero Che Guevara. Smack bang in the geographic center of Cuba, this is a city of new trends and insatiable creativity, where an edgy youth culture has been testing the boundaries of Cuba’s censorship police for years. Unique Santa Clara offerings include Cuba’s only official drag show, a graphic artists' collective that produces satirical political cartoons, and the best rock festival in the country: Ciudad Metal. The city’s fiery personality has been shaped over time by the presence of the nation’s most prestigious university outside Havana, and a long association with Che Guevara, whose liberation of Santa Clara in December 1958 marked the end of the Batista regime. Little cultural revolutions have been erupting here ever since.

Beguiling, outlandish and surreal, Baracoa's essence is addictive. On the wet and windy side of the Cuchillos del Toa mountains, Cuba’s oldest and most isolated town exudes original atmosphere.

Cuba's cultural capital, Santiago is a frenetic, passionate and noisy beauty. Situated closer to Haiti and the Dominican Republic than to Havana, it leans east rather than west, a crucial factor shaping this city's unique identity, steeped in Afro-Caribbean, entrepreneurial and rebel influences.

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.

When Pinar del Río's greenery starts to erupt into craggy mogotes (limestone monoliths) and you spy a cigar-chewing guajiro driving his oxen and plough through a rust-colored tobacco field, you know you've arrived in Viñales. Despite its longstanding love affair with tourism, this slow, relaxed, wonderfully traditional settlement is a place that steadfastly refuses to put on a show. What you see here is what you get – an agricultural town where front doors are left wide open, everyone knows everyone else, and a night out on the tiles involves sitting on a sillón (rocking chair) on a rustic porch analyzing the Milky Way.

Lovely Santiago. Far from the capital in Cuba's mountainous 'Oriente' region, this perennial hotbed of rebellion and sedition is Cuba's most 'Caribbean' enclave. The difference is invigorating and sometimes overwhelming. Cultural influences here have often come from the east, imported via Haiti, Jamaica, Barbados and Africa. There's a raucous West Indian–style carnival and a cache of folklórico dance groups that owe as much to French-Haitian culture as they do to Spanish.

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.

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.

The sandy arc of Playa Girón nestles peacefully on the eastern side of the infamous Bahía de Cochinos (Bay of Pigs), backed by one of those gloriously old-fashioned Cuban villages where everyone knows everyone else. Notorious as the place where the Cold War almost got hot, the beach is actually named for a French pirate, Gilbert Girón, who met his end here by decapitation in the early 1600s at the hands of embittered locals. In April 1961 it was the scene of another botched raid, the ill-fated, CIA-sponsored invasion that tried to land on these remote sandy beaches in one of modern history's classic David-and-Goliath struggles. Lest we forget, there are still plenty of propaganda-spouting billboards dotted around rehashing past glories.

This small but well-endowed province is Cuba at its loveliest, also guarding a precious chunk of the country's fantastical historical legacy. Sancti Spíritus Province boasts nature worth exploring. The best on Cuba’s underwhelming south coast, Playa Ancón is a stunner. And then there are mountains. Outside Trinidad, the haunting Escambray offers outstanding hiking on a network of picturesque trails.