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.

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.

A fantasy land of crinkled mountains and exuberant foliage, the Cuban Guantánamo remains a galaxy away from modern America in ambience. That doesn't stop most people associating it with the United States Guantanamo Bay Naval Base, which continues in operation, though downsized. Off the base, the region’s isolated valleys and wild coastal microclimates (arid in the south, lush in the north) are Cuba at its most mysterious and esoteric. Herein lie primitive musical subgenres, little-known Afro-Cuban religious rites, and echoes of an indigenous Taíno culture supposedly wiped out by the Spanish centuries ago – or so you thought.

The nation’s fourth-largest city serves up authentic provincial Cuba without the wrapping paper. Though the city of San Isidoro de Holguín barely features in Cuba’s tourist master plan, there’s magic and mystery here for a certain type of traveler. There's an overabundance of shiny vintage Chevys, plazas filled with uniformed school children sharing wi-fi and interactions not marred by rushing or selling. Use it as a window to life in the interior: from the religious solemnity of the annual procession climbing Loma de la Cruz to the exuberant cheers pouring forth from the oversized baseball stadium.

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.

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.

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.

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.

Santiago är hetare, flirtigare, mer avspänt och mer afrokaribiskt än resten av Kuba. Här föddes Bacardin, revolutionen och Buena Vista Social Club. Följ med till staden som är backig som San Francisco och ligger närmare Jamaica än Havanna.

Majestic, spread-out Vedado is Havana's once-notorious Mafia-run district. During Cuba's 50-year dalliance with the US, this was the city's commercial hub and, in many ways, it still is; although these days the nightlife is less tawdry, the casinos have become discos, and the hotels seem more like historical relics than havens of luxury.