Cuba

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.

It's Complicated

No one could have invented Havana. It’s too audacious, too contradictory and – despite 60 years of withering neglect – too damned beautiful. How it does it is anyone’s guess. Maybe it’s the long history of piracy, colonialism and mobster rule. Perhaps it's the survivalist spirit of a populace scarred by two independence wars, a revolution and a US trade embargo. Or possibly it's something to do with the indefatigable salsa energy that ricochets off walls and emanates most emphatically from the people. Don’t come here with a list of questions; just bring an open mind and prepare for a long, slow seduction.

A Great Art City

It may not be like the scene in Paris or New York quite yet, but Havana's art culture is one of the city's biggest surprises. The creativity is nothing new: Cuban artists have been quietly challenging cultural elites since the age of José Nicolás de la Escalera and his depictions of enslaved black people. Today the work of Escalera and others is splendidly displayed in the Museo Nacional de Bellas Artes, while newer, racier crews congregate for electrifying 'happenings' at the Fábrica de Arte Cubano or take to the streets with their rollers and brushes in Habana Vieja.

Cool Cafes & Bohemian Bars

Despite recent economic difficulties, there's rarely been a better time to visit Havana. Private businesses (from trancey cafes to indie T-shirt makers) have sparked a creative renaissance, while big-name brands from that well-known 'frenemy' in the north have yet to dilute the cultural magic. As a result, the city bursts with experimentation: here a boutique hotel where bar stools are fashioned out of bicycles, there a community project where the barbershop is also a museum. Maybe it's something they put in the mojitos, but the ability of habaneros to endure and persevere is one of their most inspiring traits.

A 500-Year History

In Havana, history is piled up like hoarded treasure in a dusty attic – except these days, thanks to proactive City Historian Eusebio Leal Spengler, the colonial thoroughfares look a little less dusty. Leal Spengler has been nailing Havana's exhausted infrastructure back together piece by piece for more than 30 years. The results are startling. Walk the streets of Habana Vieja today and you'll quickly feel a genuine connection with the past in imposing coastal fortifications and intimate, traffic-free plazas stuffed with museums. Equally engrossing are the scattered leftovers from Cuba's more recent marriages with the USA and the USSR.

Havana

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. The Bahía de Cochinos attracts more divers than mercenaries these days, while sunbathers rather than pirates invade the northern beaches of Varadero, the vast Caribbean resort and lucrative economic 'cash cow' that stretches 20km along the sandy Península de Hicacos. Providing a weird juxtaposition is the scruffy city of Matanzas, the music-rich provincial capital that has gifted the world with rumba, danzón (ballroom dance), countless grand neoclassical buildings and Santería (the province is the veritable cradle of Afro-Cuban religion). Tourists may be scant here outside of Varadero but soulful, only-in-Cuba experiences are surprisingly abundant.

Matanzas Province

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. As the focus of Spain's new colony in the 16th and early 17th centuries, Santiago de Cuba enjoyed a brief spell as Cuba's capital until it was usurped by Havana in 1607. The subsequent slower pace of development has some distinct advantages. Drive 20km or so along the coast in either direction from the provincial capital and you're on a different planet, one of rugged coves, crashing surf, historical coffee plantations and emerald hills riotous with endemism.

Santiago de Cuba Province

In this beautiful hill-studded hinterland, Cuba’s contradictions are magnified. For the visitor, there's rich landscapes ranging from the pine-scented mountains of the Sierra Cristal to the palm-fringed beaches around Guardalavaca. Holguín's beauty was first spied by Christopher Columbus who, by most accounts, docked near Gibara in October 1492 where he was met by a group of curious Taíno natives. The Taínos didn’t survive the ensuing Spanish colonization, though fragments of their legacy can be reconstructed in Holguín Province, which contains more pre-Columbian archaeological sites than anywhere else in Cuba. Perhaps something in the water breeds extremes. Fulgencio Batista, and his ideological opposite, Fidel Castro, were both reared in this province, as were dissident writers Reinaldo Arenas and Guillermo Infante. There's plenty of contrast in settings as well: the inherent Cuban-ness of Gibara contrasts sharply with the tourist swank of resort-complex Guardalavaca.

Holguín Province

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. A postcard come alive, Trinidad is one of the most intact colonial towns in the Americas, with red-tile roofs, cobblestone streets and pastel houses with castle-sized colonial doors. Its underdog rival, the city of Sancti Spíritus offers a more intangible, crumbling allure. In 2014, both celebrated their 500th anniversaries to much fanfare and an invigorated shine on their finest architecture. But there's even more: a surprisingly varied cache of oft-overlooked curiosities, including lightly trodden eco-parks, a seminal museum dedicated to guerrilla icon Camilo Cienfuegos, and the Unesco-protected Bahía de Buenavista.

Sancti Spíritus Province

Tobacco is still king on Cuba's western fingertip, a rolling canvas of rust-red oxen-furrowed fields, thatched tobacco-drying houses and sombrero-clad guajiros (country folk). The crucible of this emerald land is the Valle de Viñales, a Unesco World Heritage Site framed by a backdrop of distinctive mogotes (limestone monoliths) that nigh-on beseech you to get hiking. Playing a tuneful second fiddle is the Península de Guanahacabibes, an uninhabited wilderness chock-a-block with fertile ecosystems that abut a swath of 50-plus offshore dive sites. People primarily come here to be close to nature, basing themselves in the serene hassle-free village of Viñales. From here, huge cave complexes call for torch-lit exploration, tobacco plantations offer expert fact-finding tours, beaches invite lazy contemplation, and every horizon seems to be filled with a host of quintessential 'come to the Cuban countryside' images. So follow the fragrant aroma of tobacco and come.

Pinar del Río Province

A fantasy land of crinkled mountains and exuberant foliage, the Cuban Guantánamo remains a galaxy away from modern America in ambience. That doesn't stop most people associating it with the United States Guantanamo Bay Naval Base, which continues in operation, though downsized. Off the base, the region’s isolated valleys and wild coastal microclimates (arid in the south, lush in the north) are Cuba at its most mysterious and esoteric. Herein lie primitive musical subgenres, little-known Afro-Cuban religious rites, and echoes of an indigenous Taíno culture supposedly wiped out by the Spanish centuries ago – or so you thought. Though brutally battered by Hurricane Matthew in October, 2016, Baracoa and its rural surroundings remain the regional highlight, closely followed by the vibrant endemism of the semivirgin Parque Nacional Alejandro de Humboldt. Further west, the city of Guantánamo, perennially bypassed by most travelers, represents the Cuba rarely tasted by tourists.

Guantánamo Province

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.

Today Cuba's largest province is a mostly pancake-flat pastoral landscape of grazing cattle, lazy old sugar mill towns and, in the south, a few low-but-lovely hill ranges. It's flanked by Cuba's two largest archipelagos: Sabana-Camagüey in the north and Jardines de la Reina in the south, both almost virgin in places, though development is already underway in the cays to the north.

With its alluring architecture, illustrious citizens of note and cosmopolitan airs, the staunchly Catholic capital of Camagüey is the star attraction.

Camagüey Province

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.

The alluringly isolated countryside helped the revolutionary cause. Road-scarce Granma is one of Cuba's remotest regions, with lofty tropical mountains dense enough to harbor fugitive Fidel Castro for over two years in the 1950s.

Its isolation has bred a special brand of Cuban identity. Granma's settlements are esoteric places enlivened with weekly street parties (with outdoor barbecues and archaic hand-operated street organs), and provincial capital Bayamo is among the most tranquil and cleanest places in the archipelago.

Granma Province

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.

This region is indelibly stamped with Che's legacy and associated sights. Yet it should also win your heart for hosting the nation's most frenzied street party (Remedios), for its highs among the glimmering Escambray peaks and their adventure possibilities (around Embalse de Hanabanilla), and for its lows along the lolling white-sand strands off its northern coast (Cayo Santa María).

Villa Clara Province

Bienvenue (welcome) to Cienfuegos, Cuba's Gallic heart, which sits in the shadow of the crinkled Sierra del Escambray like a displaced piece of Paris on Cuba's untamed southern coastline. French rather than Spanish colonizers were the pioneers in this region, arriving in 1819 and bringing with them the ideas of the European Enlightenment, which they industriously incorporated into their fledgling neoclassical city: the result today is a dazzling treasure box of 19th-century architectural glitz. Beyond the city, the coast is surprisingly underdeveloped, a mini-rainbow of emerald greens and iridescent blues, flecked with coves, caves and coral reefs. The province's apex is just inland at El Nicho, arguably the most magical spot in the Sierra del Escambray. Though ostensibly Francophile and white, Cienfuegos' once-muted African 'soul' gained a mouthpiece in the 1940s with local-born Mambo king Benny Moré and in the Catholic-Yoruba Santería brotherhoods, which still preserve their slave-era traditions in the town of Palmira.

Cienfuegos Province

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.

Away from the tourist hordes, the province has been harboring intriguing secrets for over a century. Various non-Spanish immigrants first arrived here in the 19th century from Haiti, Jamaica, the Dominican Republic and Barbados, bringing with them myriad cultural rites still practiced in cricket matches in Baraguá, folk-dancing in Majagua and explosive fireworks in Chambas.