Travelling to Valparaíso, Chile, fulfilled my childhood dream: flying over the Andes. Instead of Santiago de Chile, this pulsating harbour city stole my heart.

Colourful, vibrant, artsy, quirky, rough… you quickly run out of adjectives to describe Valparaíso. Spread over steep hills (cerros) overlooking the Pacific Ocean, the city is known as the Jewel of the Pacific, but also for its rampant crime rate.

On the UNESCO World Heritage List since 2003, in the past two decades Valparaíso has attracted countless artists, creatives and cultural entrepreneurs to dwell on its panoramic hills. No wonder the city seduced me in a second. Although the amount of stray dogs broke my heart. Their sad eyes still haunt me.

After our day trip to Valparaíso with Scandinavian wine professionals (thanks to Miguel Torres Chile for amazing time in the country!), I was craving for more. Therefore, I returned to Valparaíso for my remaining solo days in Chile, confident to navigate there without a map.

Choosing the wrong elevator on the plateau, I ended up on an obscure-looking square where the locals told me to leave immediately. Still a newbie in Valparaíso, I decided to listen to them.

1. Be attentive with the hills

One of the most emblematic features of Valparaíso are its wooden, squeaky elevators (funiculars). They take you from sea level to the hills. Before going up, check carefully which elevator goes to which hill. Some hills are no-go zones.

If you pick the wrong elevator, you probably need to come back down to the plateau. Since the funicular network was reduced, some cerros have remained aloof from others – and the narrow pedestrian lanes connecting them are perfect for pickpockets.

Besides funiculars, you can move around by Valpo trolleybuses that are the oldest still-functioning trolleybuses in the world. Modern buses are more efficient and the network is comprehensive yet not all the slopes are reachable by bus. And I prefer getting to know places by walking 15 to 20 kilometres a day.

During my Valparaíso walks, the locals warned me several times about going further up on the hills. Having read stories of Valpo becoming the most dangerous city in Chile, I developed a true respect for their protective attitude.

However, with common sense and by keeping a low profile one can explore this magnificent city. Just avoid getting into the maze of upper Valparaíso alleys unless you have someone local with you.

2. Don’t let cab drivers fool you

This applies to many cities, but what happened to me in Valparaíso is a glaring example. After messing up with the elevators upon my return to the city, I opted for a taxi.

A nice-looking local guy advised me to grab an unofficial taxi and even negotiated the rate with the driver to 500 pesos. The recommended official fare for that kind of distance would have been 1,500 to 2,500 pesos.

In the end of the ride the bill was more than tenfold. But with limited understanding of Spanish, heavy suitcase and not knowing much of the city yet, what can you do?

It’s true that many streets in Valpo are one-way and zigzag, so even short distances by car may take time. Nevertheless, my street-savvy solo traveller image suffered a severe blow.

3. Fall in Love with Cerro Alegre and Cerro Concepción

These cerros are safe, beautiful and easy to reach from the plateau. If you wish to walk in peace while enjoying nice restos, cafés and bars, Alegre and Concepción are the areas to explore. Marvel at stunning graffiti and artesan boutiques in refurbished surroundings.

Based on my experience, Chile wasn’t as cheap as neighbouring Argentina. But it wasn’t hard to find a decently priced room in Valparaíso only a day before my arrival.

The location of Punto Cerro (not sure if Diego still rents rooms as he had plans of selling the house and moving to France) was perfect. Nice streets of Cerro Concepción and Cerro Alegre were just a stone throw away whilst the rooftop terrace offered stunning views to the harbour and hills.

4. Seafood & dessert at Café Turri

Thanks to its coastal location, Valparaíso is a heaven for seafood lovers. I had ceviche every day, and the fish was as fresh as it can get. There were various interpretations of this traditionally Peruvian dish in the restaurants, which made eating fun!

Oozing the charm of the old days, Café Turri offers wonderful views to the Pacific and a nice wine list. Popular for afternoon tea and cakes, Turri also had the widest menu I saw in Valparaíso; sophisticated and creative dishes for every taste.

I still savour the memory of squid lasagne with scallops and succulent pork fillet in raspberry sauce. Not to forget splendid meringue, fruit compote and butterscotch dessert (see the opening picture of this blog post).

During our lunch warm breezes caressed the coastline and the sea shimmered in every shade of blue. Even the waiter that first seemed distant gets personal, ending up cracking jokes with us.

Suddenly a big laughter is wafted from the table next to us. A bunch of bikers! Easy to approach, we end up chatting to one of them.

His name is Santiago.

5. Prepare for capricious weather

The morning mist in Valparaíso can be extremely thick and the weather surprisingly chilly until late afternoon. The nights, too, were colder than one would expect in autumn (I visited the city in the end of March), and the winds can be nasty. Even though Valpo is nothing like the Azores where the weather changes constantly, be prepared to dress in layers.

If you are short of time, take the elevator up to Cerro Artillería hill just before sunset. The view to the huge harbour of Valparaíso is spectacular! Besides, next to the funicular there are traditional wooden kiosks selling hand-made jewelry, other artworks and local delicatessen.

For a glimpse of shady neighbourhoods, neglected parks, poverty and junkies, continue deeper into this cerro. I went, nothing happened, but in the evening Diego was not very content hearing that.

6. Explore Greater Valparaíso area

If you want a break from Valparaíso’s edginess, catch a bus to adjacent Viña del Mar. Neat, nice, modern and safe, this popular beach city is favoured by many Chileans living elsewhere. In my opinion, Viña offers enough to do for a day but lacks the whimsical charm of Valpo.

I felt much more at home with another touristic hotspot, ConCón, that lies 15 kilometres North of Valparaíso. For rugged coastaö landscapes, sunbathing seals and flocks of pelicans, this is the place to be. ConCón attracts sun-lovers and outdoor people to walk on its dunes while offering excellent surfing possibilities.

7. Dinner overlooking the sea

My last evening in Valpo was very cold so I stayed near Diego’s place. For the dinner, recommends La Concepción, one of the finest and best-known restaurants in the city. It has a big terrace with terrific views to the Pacific.

Arriving early (many Chileans eat 21:00 onwards), the place is half-empty but gets crowded as the evening goes by. To my surprise, La Concepción has 50 labels on the list but not many wines by the glass. As if the waiter knew my thoughts, he suggests a bottle (and packing the rest of it in a doggy-bag).

Made of local ingredients, the food is tasty and the service is attentive to the smallest detail. As the evening gets colder, they bring me two wool blankets so that I can continue dining outside.

The first half of the bottle escorts my dinner, and the other half travels with me to Santiago on the following day. Lucky as I am, an exciting Chile vs. Argentina soccer game awaits me at Estadio Nacional Julio Martinéz Prádanos.

Café Turri: Templeman 147 (Cerro Concepción). Mon-Fri 12:30–14 and 19:30–21:30, Sat 19:30–21:30. Tel: (56) 32 236 5307 & (56) 32 225 2091, or book here.

Café Vinilo: Almirante Montt 448 (Cerro Alegre). Mon-Thu 09–01:30, Fri & Sat 09–02:30 and Sun 16–01:30. Tel: (56) 32 223 0665.

La Concepción: Papudo 541 (Cerro Concepción). Tue-Thu 12:30–22:30, Fri-Sat 12:30–23, Sun 12:30–22. Tel: (56) 32 249 8192 or book here.