Kuba

Neither Occidente nor Oriente, Camagüey is Cuba's provincial contrarian, a region that likes to go its own way in political and cultural matters – and usually does – defying expectations in Havana and Santiago. These seeds were sown in the colonial era, when Camagüey's preference for cattle ranching over sugarcane meant less reliance on slave labor and more enthusiasm to eliminate the whole system.

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.

In this beautiful hill-studded hinterland, Cuba’s contradictions are magnified. For the visitor, there's rich landscapes ranging from the pine-scented mountains of the Sierra Cristal to the palm-fringed beaches around Guardalavaca. Holguín's beauty was first spied by Christopher Columbus who, by most accounts, docked near Gibara in October 1492 where he was met by a group of curious Taíno natives. The Taínos didn’t survive the ensuing Spanish colonization, though fragments of their legacy can be reconstructed in Holguín Province, which contains more pre-Columbian archaeological sites than anywhere else in Cuba.

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.

Embellished by soaring pine trees and bulbous limestone cliffs that teeter like top-heavy haystacks above placid tobacco plantations, Parque Nacional Viñales is one of Cuba's most magnificent natural settings. Wedged spectacularly into the Sierra de los Órganos mountain range, this 11km-by-5km valley was recognized as a national monument in 1979, with Unesco World Heritage status following in 1999 for its dramatic steep-sided limestone outcrops (known as mogotes), coupled with the vernacular architecture of its traditional farms and villages.

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.

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.

Large, very detached and set to a slow metronome, La Isla is both historically and culturally different to the rest of the Cuban archipelago. Mass sugar and tobacco production never existed here, and until the Castro revolution, the island yielded to a greater American influence. Eclectic expat communities, which call on Cayman Island, American and Japanese ancestry, have even thrown up their own musical style, a sub-genre of Cuban son known as sucu sucu. Today the island, bereft of the foreign students that once populated its famous schools, is sleepy but extravagantly esoteric: with a prison masquerading as a museum and scuppered ships just waiting for you to dive down to – or to party in! The opportunities for getting (way) off the beaten track will appeal to divers, escape artists, adventurers and committed contrarians.

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.

With a name translating as 'massacres,' Matanzas Province conceals an appropriately tumultuous past beneath its modern-day reputation for glam all-inclusive holidays. In the 17th century pillaging pirates ravaged the region's prized north coast, while three centuries later, more invaders grappled ashore in the Bahía de Cochinos (Bay of Pigs) under the dreamy notion that they were about to liberate the nation.