Our guide shoots us a cheeky smile as our small posse shuffles onto the No. 612 micro bus, and battles it out with locals for a seat. "Hang on," he calls out, as the old rattler lurches into the downtown traffic and heads for the hills.
Valparaiso has 43 of them, forming an urban roller coaster, and within minutes, I'm beginning to feel like I'm on the Big Dipper. We hurtle around blind corners, dodge pot holes, speed through downhill bends, and pull up abruptly to pick up roadside passengers before swerving out again.
The views across the colourful, ramshackle houses hanging off cliffs, down to the port below, are breathtaking, but I can't fully focus on anything except the bends up ahead.
We're eventually deposited at one of the many viewpoints along the way, Plaza Bismarck, collectively grateful to have been spared the trek uphill on our official walking tour of the city, but relieved to exit one crazy ride.
The "O Route", as it turns out, is famous for connecting about 14 of Valparaiso's hills (called cerros in Spanish). The bus ride takes the route seen in the film, The Motorcycle Diaries, of revolutionary Che Guevara's arrival into Valparaiso, and for the princely sum of one US dollar, it surely represents amazing value for money – provided your nerves are up for it. Our guide explains that the drivers on this privatised bus system operate on commission; the incentive is to get around their circuit as fast as possible. It's certainly a novel concept.
We've exited at Cerro Carcel and recommence our walking tour with Leonardo. Born in Valparaiso, but having lived in the US for most of his 20s, his world view and local knowledge are as expansive as his English, and our group fires questions at him: everything from best local haunts to cultural insights. He nods in the direction of Calle Cumming, a street that looks pretty bland up where we are, but apparently weaves down into a network of buzzing bars and restaurants as it gets closer to downtown. I make a mental note for that night.
After taking in the market stalls and sensational ocean views from the terrace of Plaza Bismarck, our tours winds through the back streets and mish-mash of housing that leads to Parque Cultural, where the old prison has been turned into an arts collective.
Under General Pinochet's rule, the bleak cell block, with its tiny grilled windows, was a place of misery for political prisoners; today it's been reinvented as an arts space, open weekends for tours. Directly opposite, across a green lawn, is an ultra-modern cultural theatre. The parque's location high on the hill, a stone's throw from two old cemeteries, makes it a lonely landmark befitting its past. Our guide assures us many of Valparaiso's older citizens refuse to step foot inside, the years of tyranny still all too vivid.
We start to wend our way back down to the port, skirting around the edges of Cerro Concepcion and Cerro Alegre, the rich, gentrified neighbourhoods favoured by tourists, yet far from "touristy". First and foremost, they're residential suburbs, and locals go about their business largely oblivious to the visiting crowds.
Concepcion is where our hotel is, nestled among interesting shops, bars, restaurants, impressive residences, local hangouts, and steep, cobbled streets, steps and alleyways, where amazing graffiti is commonplace. We're talking about murals that stretch for a whole street block, morphing from one scene to another in giant swirls of colour and detail.
It's what this port city, just 120 kilometres from Santiago, is most famous for and it's pretty much everywhere. Valparaiso's local government embraces street art, as it clearly brings in the tourist dollars and showcases some extraordinary artistic feats – both in terms of creativity and sheer scale. As a result, retailers are generally happy to have artists turn their plain walls into works of art.
We descend via steps and winding streets until we're almost back where we started, in central Plaza Sotomayor, the heart of the historic district by the port. While the city buildings look imposing, the reality is that Valparaiso was largely destroyed by a devastating earthquake and fire in 1906, so much of what you see downtown has been rebuilt or faithfully restored.
For example, the grand, blue-coloured Armada Building, headquarters of the Chilean navy, which takes pride of place on Plaza Sotomayor, was actually built in 1910, replacing the original naval building on the site.
Valparaiso was declared a UNESCO World Heritage Site in 2003, hailed as "an exceptional testimony to the early phase of globalisation in the late 19th century, when it became the leading commercial port on the sea routes of the Pacific coast of South America". The opening of the Panama Canal in 1914 and subsequent change in trade routes put paid to that, but the city certainly retains the fabric of its hallowed past.
Aside from the lively port district, many of the original funiculars are still in use, offering cheap transport up the hills, as well as panoramic views.
The city's oldest, Ascensor Concepcion (built 1883), takes you to Paseo Gervasoni, at the lower end of Cerro Concepcion. In the evening, as we discovered, it's a favourite hangout for the area's youth, who gather for a few beers in the paved area at the top of the funicular. In gregarious Latino style, they were most accepting of stragglers joining their informal party.
Just off Plaza Sotomayor is Ascensor El Peral that goes up to Cerro Alegre, home to the Palacio Baburizza, which now contains the city's Museo de Bellas Artes.
Valparaiso really has it all: a gritty bohemian soul, colourful history, an excellent food and bar scene, and compelling street art. And those soaring hills, knitted together by stairways, laneways and the rattling funiculars.
In the words of one of its most famous former residents, Nobel Prize-winning poet Pablo Neruda, whose La Sebastiana house at Ricardo de Ferrari 692 is a must-see:
"Valparaiso, what an absurdity you are, how crazy: a crazy port. What a head of dishevelled hills, that you never finished combing. Never did you have time to dress yourself, and always you were surprised by life."
As we discovered, "Valpo" is actually a very viable alternate stopover, especially if you've already exhausted Santiago's offerings. With the direct Qantas 12½-hour flight from Sydney arriving into the capital late morning, you can be settled into your Valparaiso digs and enjoying a cocktail by late afternoon in one of the many hillside bars.
Isobel King travelled at her own expense.
Valparaiso is 120 kilometres from Santiago. Buses leave regularly from Pajaritos bus terminal (about 15 minutes by taxi from the airport) for the 1½-hour journey to Valparaiso. See turbus.cl
MM450 is a charming boutique hotel, with flowing outdoor terraces and excellent restaurant. Set on a quiet street in Cerro Concepcion, it's a short stroll to all the action on the hill. Rooms from $140 per night. See mm450.cl
Tours 4 Tips offers a choice of walking tours of the city. While notionally free, it's customary to tip for the three-hour walking tours; about $US10 to $US15 tip is typical. See tours4tips.com