Kuba

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.

Varadero, located on the sinuous 20km-long Hicacos Peninsula, stands at the vanguard of Cuba’s most important industry – tourism. As the largest resort in the Caribbean, it guards a huge, unsubtle and constantly evolving stash of hotels (over 60), shops, water activities and poolside entertainment; though its trump card is its beach, an uninterrupted 20km stretch of blond sand that is undoubtedly one of the Caribbean's best. But, while this large, tourist-friendly mega-resort may be essential to the Cuban economy, it offers little in the way of unique Cuban experiences.

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.

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.

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.

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.

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.

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.

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.

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.