Kuba

Trinidad is one of a kind, a perfectly preserved Spanish colonial settlement where the clocks stopped in 1850 and – apart from a zombie invasion of tourists – have yet to restart. Huge sugar fortunes amassed in the nearby Valle de los Ingenios during the early 19th century created the illustrious colonial-style mansions bedecked with Italian frescoes, Wedgwood china and French chandeliers.

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.

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.

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.

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.

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.

Tobacco is still king on Cuba's western fingertip, a rolling canvas of rust-red oxen-furrowed fields, thatched tobacco-drying houses and sombrero-clad guajiros (country folk).

La Victória de Las Tunas (as it's officially known) is a sleepy agricultural town anointed provincial capital. It has long held a sleazy reputation for being the Oriente's capital of sex tourism. But thanks to good private lodgings, welcoming locals and a handy location on Cuba's arterial Carretera Central, handfuls of road-weary travelers drop by and are pleasantly surprised. Missing here are the touts that exasperate tourists in other destinations. It's a window into real provincial life.

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.

Playa Larga, several kilometers south of Boca de Guamá at the head of the Bahía de Cochinos (Bay of Pigs), was one of two beaches invaded by US-backed exiles on April 17, 1961 (although Playa Girón, 35km further south, saw far bigger landings). Nowadays, it's the best base for exploring the Zapata peninsula, Cuba's largest wilderness area, and is also known for its diving (although Playa Girón makes a better base for the latter activity). There's a cheapish resort here, a scuba-diving center, and a smattering of casas particulares in the adjacent beachside village of Caletón.