Kuba

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.

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.

When Pinar del Río's greenery starts to erupt into craggy mogotes (limestone monoliths) and you spy a cigar-chewing guajiro driving his oxen and plough through a rust-colored tobacco field, you know you've arrived in Viñales. Despite its longstanding love affair with tourism, this slow, relaxed, wonderfully traditional settlement is a place that steadfastly refuses to put on a show. What you see here is what you get – an agricultural town where front doors are left wide open, everyone knows everyone else, and a night out on the tiles involves sitting on a sillón (rocking chair) on a rustic porch analyzing the Milky Way.

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.

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.

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.

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.

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.

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.

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.