Pinar del Río
Surrounded by beautiful verdant countryside and given an economic boost by its proximity to the world’s best tobacco-growing terrain, the city of Pinar del Río emits a strange energy, exacerbated by its famous jineteros (hustlers) who can abrade the most thick-skinned traveler.
When you spy a cigar-chewing guajiro driving his oxen and plough through a rust-colored tobacco field, you know that you must be within striking distance of 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.
Parque Nacional Viñales
Parque Nacional Viñales' extraordinary cultural landscape covers 150 sq km and supports a population of 25,000 people. A mosaic of mogote-studded settlements grow coffee, tobacco, sugarcane, oranges, avocados and bananas on some of the oldest, most tradition-steeped landscapes in Cuba.
Parque Nacional Península de Guanahacabibes
Flat and deceptively narrow, the elongated Península de Guanahacabibes begins at the straggled-out village of La Fe, itself 94km southwest of Pinar del Río or 29km southwest of the western terminus of Cuba's railway in Guane. In 1987, 1015 sq km of this uninhabited sliver of idyllic coastline was declared a Biosphere Reserve by Unesco – one of only six in Cuba.
Península de Guanahacabibes
As the island narrows at its western end, you fall upon the low-lying and ecologically rich Península de Guanahacabibes. One of Cuba's most isolated enclaves, it once provided shelter for its earliest inhabitants, the Guanahatabeys. A two-hour drive from Pinar del Río, this region lacks major tourist infrastructure, meaning it feels far more isolated than it is.
San Diego de Los Baños
Sitting 130km southwest of Havana, this nondescript town just north of the Carretera Central is popularly considered the country's best spa location. As with other Cuban spas, its medicinal waters were supposedly 'discovered' in the early colonial period when a sick slave stumbled upon a sulfurous spring, took a revitalizing bath and was miraculously cured.
Around San Diego de los Baños
With rough roads and precious little accommodation, the untamed Sierra de Güira, a medley of limestone karst cliffs and swooping pockets of forest west of San Diego de los Baños, is off the tourist radar. This didn't prevent it becoming a retreat for the Revolution's most renowned figures in the past and, to this day, a host of rare birdlife.
The Northern Coast
Considering their relative proximity to Havana, Pinar del Río province's northern shores are largely unexplored. Facilities are sparse and roads are rutted, though visitors who take the time to make the journey out have reported memorable DIY adventures, famously hospitable locals… and of course those fantastic beaches.
Becalmed at the end of a long, bumpy road, the fishing village of Puerto Esperanza (Port of Hope), 6km north of San Cayetano and 25km north of Viñales, isn't sleepy so much as veritably slumbering. The clocks haven't worked here since…oh…1951. According to town lore, the giant mango trees lining the entry road were planted by slaves in the 1800s.
Playa Mulata Area
Squeezed into the edge of the province on the road to Bahía Honda, the countryside around Playa Mulata is the domain of guajiros, meditative cattle and the occasional fisher. Away beyond the roughshod beaches rears the ridge of the Pan de Guajaibón, one of western Cuba's highest peaks.
A quiet fishing village 25km south of Pinar del Río through exquisite countryside, La Coloma has the best beach on the province's south coast in delightful Las Canas. You can arrange boat trips from here to the still-lovelier Cayos de San Felipe. Public transport: you're joking, right? Visit strictly under your own steam/wheels.