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.

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.

Spread out like a fan on three sides of downtown, Havana's little-visited suburban municipalities hide a handful of disparate sights that can make interesting half-day and day trips from the city center. Santiago de las Vegas and Santa María del Rosario are former rural settlements that have been incorporated into the larger metropolis without losing their soporific airs; San Francisco de Paula trades off its association with famous former resident, Ernest Hemingway; Arroyo Naranjo encircles the city's largest green space, Parque Lenin, and hosts Havana's expansive botanical gardens.

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.

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.

What is that word hanging in the air over Villa Clara, one of the nation's most diverse provinces? 'Revolution,' perhaps? And not just because Che Guevara liberated its capital, Santa Clara, from Batista's corrupt gambling party to kick-start the Castro brothers' 58-year (and counting) stint in power. Oh, no. Ultra-cultural Santa Clara is guardian of the Cuban avant-garde (having the nation's only drag show and its main rock festival). Meanwhile, the picturesque colonial town of Remedios and the beach-rimmed Cayerías del Norte beyond are experiencing Cuba's most drastic contemporary tourist development.

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.

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.

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.

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.