Kuba

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.

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.

On first impressions, Havana can seem like a confusing jigsaw puzzle, but work out how to put the pieces together and a beautiful picture emerges.

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.

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.

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.

Vagabonds guide till Santiago. Tips på sevärdheter, restauranger, boenden, bästa musikställena och mycket mer.

Situated in the Archipiélago de Sabana-Camagüey, or the Jardines del Rey (King’s Gardens) as travel brochures prefer to call it, Cayo Coco is Cuba's fourth-largest island, a 370-sq-km beach-rimmed key that is unashamedly dedicated to tourism. The area north of the Bahía de Perros (Bay of Dogs) was uninhabited before 1992, when the first hotel – the Cojímar – went up on adjoining Cayo Guillermo. The bulldozers haven't stopped buzzing since.

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.

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.