Middle Chile

Syncopated, dilapidated, colorful and poetic, Valparaíso is a wonderful mess. Pablo Neruda, who drew much inspiration from this hard-working port town, said it best: 'Valparaíso, how absurd you are…you haven't combed your hair, you've never had time to get dressed, life has always surprised you.'

But Neruda wasn't the only artist to fall for Valparaíso's unexpected charms. Poets, painters and would-be philosophers have long been drawn to Chile's most unusual city. Along with the ever-shifting port population of sailors, dockworkers and prostitutes, they've endowed gritty and gloriously spontaneous Valparaíso with an edgy air of 'anything goes.' Add to this the spectacular faded beauty of its chaotic cerros (hills), some of the best street art in Latin America, a maze of steep, sinuous streets, alleys and escaleras (stairways) piled high with crumbling mansions, and it's clear why some visitors spend more time here than in Santiago.

Protected by mountains on all sides, this sun-scorched parcel of vines and orchards produces Chile's best red wines. Production started here shortly after the conquest in the mid-16th century with the introduction of vineyards by Jesuit missionaries. The mining boom of the late 19th century brought wealth and noble grapes of French origin, including Carmenere, which was rediscovered here in the 1990s after disappearing in Europe. It's now Chile's signature grape.

The town of Santa Cruz has a few good hotels and a picturesque plaza, and serves as your central departure point. But the real encanto (charm) here is heading to the countryside to learn about wine, visit with eccentric vintners and experience the lyrical pull of wine country.

Pirates, shipwrecks, political prisoners and (perhaps!) buried treasure all make cameo appearances in the Hollywood-worthy history of this remote chain of small volcanic islands 667km west of Valparaíso. This is the place where castaway Alexander Selkirk (inspiration for Daniel Defoe's Robinson Crusoe) whittled away lost years scampering after goats and scanning the horizon for ships. Once an anonymous waypoint for marauders, sealers and war ships, the archipelago was later declared both a national park and a Unesco Biosphere Reserve, with 62% of its flora found nowhere else on Earth.

There are three main volcanic islands in the chain. Robinson Crusoe, previously known as Más A Tierra, is the main tourist hub, while Alejandro Selkirk and Santa Clara islands are seldom visited. Small-scale sustainable tourism is the shared mantra, with hiking, diving and fishing the biggest draws.

The great range of challenging hikes at this well-organized, easily accessible national park will leave you as short of breath as the fabulous views. Its 121 sq km cover high-Andean steppes, lagoons and deciduous forest that turns a glorious gold and red in the fall. Pudú deer, Patagonian foxes and Pampas cats also live here, though sightings are uncommon.

Magic is alive in this tranquil farming village 13km north of Cobquecura. Steep slopes covered with lush greenery surround the settlement, lending it a tropical air. Despite growing interest from tourists and surfers, the pace of life is slow here: oxen-pulled carts are still a common sight. It's also a famous fishing spot – corvina (sea bass) apparently jump onto any hook dangled off the beach.

Dunes and scrubland separate the desolate black-sand beach from the main road, which runs parallel to the shore before looping through the small town center to the beach. A couple of wooden walkways also connect the road and the sand.

Clean and orderly Viña del Mar is a sharp contrast to the charming jumble of neighboring Valparaíso. Manicured boulevards lined with palm trees, stately palaces, a sprawling public beach and beautiful expansive parks have earned it the nickname of Ciudad Jardín (Garden City). Its official name, which means 'Vineyard by the Sea,' stems from the area's colonial origins as the hacienda of the Carrera family. Not many foreign travelers stay here, opting instead for a day trip from Valparaíso. Nevertheless, Viña remains a popular weekend and summer destination for well-to-do Santiaguinos – and the carrete (partying) here is first rate.

The southern slopes of 3122m-high Volcán Chillán are the stunning setting of this ski mecca. Unusually for Chile's ski resorts, many of its 40 runs track through forest, and there's a good mix of options for beginners and more experienced skiers.

The Maule Valley, a hugely significant wine-producing region for Chile, is responsible for much of the country's export wine. The specialty here is full-bodied cabernet sauvignon, though intriguing bottles of old-vine Carignan and País are the real stars.

Many visitors use Talca as a base for exploring the wineries and the nearby Reserva Nacional Altos de Lircay. Ask for the free Región del Maule booklet at Sernatur in Talca for great information (in English) on recommended treks, local tips and a guide to regional flora and fauna.