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.
Habana del Este is home to Playas del Este, a multiflavored if slightly unkempt beach strip situated 18km east of Habana Vieja. While the beaches here are sublime, the accompanying resorts aren't exactly luxurious. Rather, Playas del Este has a timeworn and slightly abandoned air, and aspiring beach loungers might find the ugly Soviet-style hotel piles more than a little incongruous. But for those who dislike modern tourist development or are keen to see how Cubans get out and enjoy themselves, Playas del Este is a breath of fresh air.
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.
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.
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.
In any other country, this attractive colonial city would be a cultural tour de force. But cocooned inside illustrious Sancti Spíritus Province, second fiddle to Trinidad, visitors barely give it a glance. For many therein lies the attraction. Sancti Spíritus is Trinidad without the touts. You can dine, listen to boleros on the plaza or search for a casa particular without hassle.
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.
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.
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.