Cuba

Leap-frogged by almost all international visitors, Cuba’s two smallest provinces, created by dividing Havana Province in half in 2010, are the preserve of more everyday concerns – like growing half of the crops that feed the nation, for example. But in among the patchwork of citrus and pineapple fields lie a smattering of small towns that will satisfy the curious and the brave.

The most interesting corner is Las Terrazas and Soroa, Cuba’s most successful ecoproject and an increasingly important nexus for trekking and birdwatching. East of Havana, Jibacoa’s beaches are the domain of a trickle of Varadero-avoiding tourists who guard their secret tightly. Wander elsewhere and you’ll be in mainly Cuban company (or none at all) contemplating sugar-plantation ruins, weird one-of-a-kind museums, and improbably riotous festivals. For a kaleidoscope of the whole region take the ridiculously slow Hershey train through the nation’s proverbial backyard and admire the view.

Artemisa & Mayabeque Provinces

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.

Further east, Cayo Largo del Sur is La Isla's polar opposite, a manufactured tourist enclave renowned for its wide, white-sand beaches.

Isla de la Juventud & Cayo Largo del Sur

Most travelers say hello and goodbye to Las Tunas Province in the time that it takes to drive across it on the Carretera Central – one hour on a good day. But, hang on a second! With laid-back, leather-skinned cowboys and poetic country singers, the province is known for daredevil rodeos and Saturday-night street parties. Here barnstorming entertainment is served up at the drop of a sombrero.

Although historically associated with the Oriente, Las Tunas Province shares many attributes with Camagüey in the west. The flat grassy fields of the interior are punctuated with sugar mills and cattle ranches, while the eco-beaches on the north coast remain wild and lightly touristed by Varadero standards.

In this low-key land of the understated and underrated, accidental visitors can enjoy the small-town charms of the provincial capital, or head north to beaches off the old mill town Puerto Padre where serenity rules.

Las Tunas Province

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. Trailblazing characters and a resounding sense of historical destiny define it. Diego Velázquez de Cuéllar made Santiago his second capital, Fidel Castro used it to launch his embryonic revolution, Don Facundo Bacardí based his first-ever rum factory here, and nearly every Cuban music genre from salsa to son first emanated from these dusty, rhythmic and sensuous streets. Caught dramatically between the indomitable Sierra Maestra and the azure Caribbean, the colonial casco histórico (historical center) retains a time-worn air reminiscent of Salvador in Brazil or forgotten New Orleans. So don't let the hustlers, the speeding Chevys or the clawing heat defeat you. There's untold magic here too.

Santiago de Cuba

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. Camagüey's pastel colonials and warren-like streets are inspiring. Get lost for a day or two exploring hidden plazas, baroque churches, riveting galleries and congenial bars and restaurants. The flip side is that there is a higher-than-average number of jinteros (touts) who can dog you as you stroll. In 2008, Camagüey's well-preserved historical center was made Cuba's ninth Unesco World Heritage Site and in 2014 the city celebrated its quincentennial.

Camagüey

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.

Habana Vieja

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. Aside from its small clutch of modernist rascacielos (skyscrapers), Vedado is a largely leafy residential quarter bisected by two wide Parisian-style boulevards and anchored by the bombastic Plaza de la Revolución and the beautifully eerie Necrópolis Cristóbal Colón.

Vedado

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. Although Guardalavaca is nearby, there's little focus on tourism in the provincial capital. You won’t find tour groups milling the streets in migratory herds, but you will find an easy authenticity. Think eager-to-please casas particulares, cheap food in pioneering restaurants and a city that loves – and brews – its own beer.

Holguín

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. Declared a World Heritage Site by Unesco in 1988, Cuba's oldest and most enchanting 'outdoor museum' attracts busloads of visitors. Yet the cobblestone streets, replete with leather-faced guajiros (country folk), snorting donkeys and melodic troubadours, retain a quiet air. Come nightfall, the live-music scene is particularly good. Trinidad is also ringed by sparkling natural attractions. Twelve kilometers south lies platinum-blond Playa Ancón, the best beach of Cuba’s south coast. Looming 18km to the north, the purple-hued shadows of the Sierra del Escambray (Escambray Mountains) offer a lush adventure playground with hiking trails and waterfalls.

Trinidad

In his song 'Cienfuegos,' Benny Moré described his home city as the city he liked best. He wasn't the settlement's only cheerleader. Cuba's so-called 'Pearl of the South' has long seduced travelers from around the island with its elegance, enlightened French airs and feisty Caribbean spirit. If Cuba has a Paris, this is most definitely it. Arranged around the country's most spectacular natural bay, Cienfuegos is a nautical city founded in 1819 by French émigrés, whose homogeneous grid of elegant classical architecture earned it a Unesco World Heritage Site listing in 2005. Geographically, the city is split into two distinct parts: the colonnaded central zone with its stately Paseo del Prado and graceful park; and Punta Gorda, a thin knife of land slicing into the bay with a clutch of outrageously eclectic palaces built by the moneyed classes in the 1920s.

Cienfuegos

Beguiling, outlandish and surreal, Baracoa's essence is addictive. On the wet and windy side of the Cuchillos del Toa mountains, Cuba’s oldest and most isolated town exudes original atmosphere. Feast your eyes upon deep green foliage that's wonderfully abundant after the stark aridity of Guantánamo’s south coast. Delve into fantastical legends, and acquaint yourself with an unorthodox cast of local characters. There’s Cayamba, the self-styled ‘Guerrilla troubadour’ who once claimed he was ‘the man with the ugliest voice in the world;’ La Rusa, an aristocratic Russian émigré who inspired a novel by magic-realist author Alejo Carpentier; and Enriqueta Faber, a French woman who passed herself off as a man to practice as a doctor and marry a local heiress in Baracoa’s cathedral in 1819 – likely Cuba’s first same-sex marriage. Baracoa – what would Cuba be without you? While 2016's Hurricane Matthew hit Baracoa hard, the town is already on the rebound.

Baracoa

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. Most Varadero tourists buy their vacation packages overseas and are content to idle for a week or two enjoying the all-inclusiveness of their resort (and why not?). However, if you’re touring Cuba independently, and want to swap your backcountry rambling for some stress-free beach life, Varadero can provide a few nights of well-earned sloth after a dusty spell on the road.