Valparaiso was once known as “The Jewel of the Pacific” – attracting European immigrants from the UK, Germany and Italy and serving as a main stopping point for ships from the Atlantic and the Pacific.
As one of the Pacific’s most important seaports, Valparaiso enjoyed a heady golden age between 1848-1914. Wealthy families built magnificent mansions on the hillsides and as head of the Chilean Navy since 1817, the magnificent Edificio Armada de Chile was built on the Plaza Sotomayor.

With its strategic location, Valparaiso seemed destined for greatness, but two significant events reversed the city’s fortunes. In 1906, a massive earthquake destroyed many of the city’s buildings and killed over 3000 inhabitants. Just eight years later, in 1914, the Panama Canal opened and Valparaiso’s importance as a seaport dropped significantly.
Wealthy families began to abandon the city, and the slow and steady decline began. By the early 1990’s, Valparaiso was in serious economic trouble. As is often the case, attracted by low rents and abandoned buildings, the artists moved in. Entrepreneurs began to develop restoration initiatives and the city underwent a transformation as artists covered the bleak and rundown walls with murals.
Toward the beginning of the 21st century, attracted by the Valparaiso’s mushrooming cultural scene, a robust university atmosphere and colourful houses clustered on narrow and hilly cobblestoned streets, tourists began to flock to the city. Valparaiso became a cruise ship destination and in 2003, Valparaiso was declared a UNESCO World Heritage site.
All of this information was imparted to us by the knowledgable and gregarious Camilio, a guide with the Tours4Tips free walking tour company.
We were only in Valparaiso for one day, which was a mistake on our part. Originally we had planned to end our trip with a week in Santiago and a few days in Valparaiso, but in researching both cities, I was reading a worrying number of articles about how unsafe Valparaiso had become.
This was reinforced by talking to a number of Chilean locals. “Ah, si, peligroso,” they would sigh, as thought they felt somehow responsible.
Well, there is dangerous (armed holdups and kidnappings) and there is “dangerous“( pickpockets) and Valparaiso falls into the latter category. If you stay in the main tourist areas, you need to watch your stuff and behave with common sense. If you venture out of the tourist areas, it might be a different story.
We got as much as we could out of a day trip from Santiago (90 minutes by bus each way) but we missed out on seeing one of Pablo Neruda’s homes, spending more time walking the hills, visiting Vina del Mar, and taking a wine tour in nearby wine country.
So…here is our day in Valparaiso, in all its truncated glory, enroute from the bus station to Plaza Sotomayor, to meet our walking tour group.
Everywhere is a study in contrasts: daily life with splendid old architecture next door to modest hill homes and food kiosks on the sidewalks.

Some streets are more modest than others – in this case, there is little evidence of restoration, but life goes on.

Which brings us to one of Valparaiso’s sticking points – being awarded the UNESCO World Heritage site is its blessing and its curse. While the award carries prestige and attracts tourism, it also compels the municipality to maintain the heritage aspects named in the award – in this case, the buildings in the historic centre and the funiculars – but it does not provide financial assistance.
For a cash-strapped city like Valparaiso, it can become a monstrous financial handicap. Developers are not permitted to tear down historic buildings, but they are less inclined to want to tackle the challenging task of restoring them, so many sit empty.
Valparaiso is famous for its funiculars – those almost-vertical ascensores that climb the city’s many hills. The funiculars were built in the late 19th and early 20th century – at one time there were 30. Currently there are 16, but a number of them are closed for restoration. The two main funiculars travel to the historic centre – Alegre and Concepcion.

We hopped on this funicular in the afternoon – a mildly unnerving ride that is over almost as soon as it begins and costs the very reasonable sum of 100 pesos (20 cents). More on that later – back to the walking tour.
Our group of 12 met up at the square – the usual mix of Europeans (Belgian, Dutch, French and Italian) and us. Camilio began with an introduction to the area – the oldest in the city, and a brief history of Valparaiso’s rise and fall. We boarded a bus that took us high up into the hills (there are anywhere from 40-44 hills, depending upon definition and each one constitutes a neighbourhood.)
From our first vantage point we gazed out over the seaport. Valparaiso is still the main seaport for passenger and cargo transport in Chile.

Looking in the other direction, Camilio pointed out the nearby town of Vina del Mar in the distance – Valparaiso’s upscale neighbour. As well as being a more polished town, Vina del Mar has better beaches. The Humboldt current sweeps its strong icy currents into Valparaiso’s crescent and swimming is not advised.

From another vantage point we were able to see neighbourhoods that by virtue of their isolation from easy public transportation are neglected and best avoided. The general rule of thumb in Valparaiso, much like Medellin, Colombia is this: the higher up the hill, the less advantaged the neighbourhood.

The three houses in the foreground (yellow, red and blue) are iconic Valparaiso landmarks; featured on book covers, postcards and thousands of Instagram shots. They embody the classic German-inspired architecture and the rich vibrant colours for which the city is noted.

Our next stop was at Carcel Hill – the site of the infamous old jailhouse. This Dickensian building was in operation from 1907 until the end of the 20th century and housed everyone from hardened criminals to petty thieves to political dissidents.
During Pinochet’s regime, many of his opponents were detained, tortured and jailed here, with already horrific conditions made worse by overcrowding and territorial disputes among existing prisoners against the detainees.
Closed in 2000, this building sat empty and the grounds became a neglected and dangerous playground for drug users and prostitutes. Eventually, a major cleanup project began, the night-time hooligans were chased away and in 2010 the jailhouse was transformed into an art gallery, and urban cultural centre.

It was at this site that Camilio sat us down to discuss “a delicate subject.” The former jailhouse was a perfect backdrop to talk about the tumultuous Pinochet era and Camilio spoke candidly about his feelings on the subject. What was a huge surprise for most of us was the fact that 33 years later, talking about Pinochet remains a touchy subject, especially among Chileans old enough to have been directly affected. People are extremely divided on the subject and some people still revere the man.
Older people who opposed the regime and carry the scars of that traumatic time do not feel comfortable expressing opinions openly and are mistrustful of police and authority. Incredibly, the Pinochet era is not taught in school, other than a few sentences that mention him as having being a president. The history is being distorted and buried, in large part by people from that time who are still in power.
Camilio told us about how a new Constitution had been written to supposedly expand and protect human rights, but it was overseen by a right-wing faction who spread “fake news” to constituents that if they voted “no” they could have their homes seized. So the fear and the power still exists and the young Chileans are frustrated and angry.
Another Constitution is planned but in May there will be a vote to decide on the people responsible for writing the documents in a more just and democratic fashion. Camilio and his generation are holding their breath that this might finally be a turning point.
And, as is so often the case when political views are being repressed, they find their way out in art and music. We walked down this street filled with tags and slogans – all of them there illegally.

For every graffiti with a message, there is another one that is simply art for art’s sake.

Murals lining the wall along a staircase.

Paint is not the only media – mosaic tile can be found in a number of spots.

Our walk back down to the port took us through some interestingly gritty neighbourhoods.


And so our tour ended – leaving us with a few hours to explore on our own. We took the funicular up to Cerro Alegre, which is where you would want to stay if you were visiting Valparaiso.
Away from the chaos and dinginess of the port level, Cerro Alegre offers a whole other side of the city. Democratic views, delightful wall art, well-kept homes and streets full of shops and restaurants.

This neighbourhood has serious hills – check your brakes and your hamstrings before setting out.

Every corner brings either an ocean view, a compelling piece of art, or both.

Painting murals is ongoing – we walked by this work-in-progress.

And reluctantly, we headed back to the bus station for the ride back to Santiago. Along the way, we drove by some of Chile’s famous wine country. Again, a destination we missed and will have to make up the next time.


We have just a few more days in Santiago and our trip is over. I’ll send out one last posting.
Well at least you saw some nice artwork!!
Loved the funiculaires !
Vina del Mar is just a popular resort! Not worthet seeing!!
Pablo Neruda has also a house in Santiago well worth a visit if you still have the time!!
Glad you decided to visit Chile, we still love it!
Have a safe trip back home and please bring sun and warmth with you it has been so depressing here!!
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We went to Pablo Neruda’s house in Santiago yesterday – what a life he lived! We love Chile as well, and are keen to see more of this country. You realize how many layers there are to peel back, and of course being a foreigner with a limited grasp of language, it is difficult to talk to residents about their lives.
We’ve really enjoyed meeting people from all three countries – they have been so warm and humorous and curious and welcoming.
We’ve been checking the weather forecast for our return – it’s looking pretty nice – sunny and high teens!
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Always love your posts Ginny, you must have a wonderful man to inspire you 🤪🤪 Gord McDonald… Sounds like you are both healthy and happy👍
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Gord! How did you guess my secret? Life is always better with a wonderful man. :>)
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We did not spend time in Valparaiso when we were there as it was considered dangerous at that time so you have given us a glimpse of a new version of the city. I can’t believe the murals. They are special. Hope you enjoy your last few days in Santiago.
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Jeanne, I think we missed the best murals – apparently there is a spot called Open Sky and there are a huge collection of murals there. It would have been better if we had had two or three days there, but such is life. It’s not possible to see everything and there are always places you feel you could have stayed longer as well as those where you stayed longer than you might have liked.
We still feel like two very lucky people.
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It seems like the “Jewel of the Pacific” is not quite what it was when it was first named, but then, all things change in time, do they not? In spite of the fact that you only had one day to spend on the sights, you managed to learn a great deal and take a lot in (as you always do!)
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It’s so true about change, although from Jeanne’s comment, it sounds as though Valparaiso has been a bit edgy for decades. It’s such a shame because it is a beautiful city, in a lovely setting.
You can get a lot done in one day, but we did feel like we left a lot behind.
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Love reading your blobs and enjoying the photography but cannot wait for you to get home
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That should read BLOGS!
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Funny! It will be great to see you and Jon – we’ll be in touch as soon as we’re back.
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Oh my you two have seen and taken in so much! And, did I read something about wineries when you return? You both look so well in the travelling life.
Thank you for your blog Ginny! I’ve enjoyed and learned so much in your writing.
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