Have you ever visited a city in a foreign country and said to yourself, “I could live here”? We’ve had this feeling only a couple of times in our lives. The most notable time was when we visited Sydney, Australia a couple of years ago. When we returned home, we said this to our son: “If we had visited Sydney 30 years earlier, you would be Australian instead of Canadian!” More recently, we had a similar experience: perhaps not quite as passionate, but close. We thought the same thing when we visited Santiago, the capital of Chile: We could live there. And we don’t even speak Spanish. But back to the beginning of our Santiago story.

We arrived in Chile not at an airport after a tiring 10-hour flight (that would come later – on our way home), rather via cruise ship – cool, collected, rested and met at the terminal by our wonderful “Tours-by-Locals” guide, Leo. We had arranged a four-day Santiago-area sojourn that we hoped would give us the flavour of the city and beyond –wine and mountains were calling to us.

The wonderfully personable Leo also turned out to be a passionate and exceptionally knowledgeable Chilean who generously shared the secrets of his country. We were in for a real treat. That treat began with our tour of the port city of Valparaiso before the inland trip to Santiago and the Andes.

The most striking thing about Valparaiso was the street art. Much more than what we have come to know as graffiti, this street art provides the true essence of this port city that is past its heyday. The opening of the Panama Canal (which we had recently transited) made sure of that. Before ships could make their way from Europe and the east coast of North America via that shortcut, they had no choice but to round the southern tip of South America and make their way north along the coast. Valparaiso was a major stop on that route. But no longer.

After getting a sense of Valparaiso, Leo took us up the coast to Vina del Mar, a seaside bedroom and vacation community before heading inland via the very well-maintained, four-lane divided highway.

As we entered Santiago proper, the first thing we were struck by is the ever-present Andes. Every time you look up you could swear that you weren’t in a big city because all you can see in the distance is mountains. The city lies in the country’s central valley about 1700 feet above sea level. A city of some 6 million people, Santiago is also one of the oldest of the major metropolises in the Americas. It was founded in 1541 by the Spanish conquistador Pedro de Valdivia. What makes this city especially interesting is the juxtaposition of the old – represented by the centre of the grid-like old city and the exquisite examples of modern architecture. Like our home town of Toronto, it is also a city of neighbourhoods, each with its own character.

The old city square is not a place you want to meander through without ensuring the safety of your wallet. Gazing around at the old and the new, you might forget that you are also surrounded by throngs of unemployed immigrants hanging around either doing very little or waiting for jobs as Leo explained.

We stayed at the Renaissance Hotel which is located in a leafy, upscale residential area known as Viticura. As Leo explained, each of these districts within the city has its own mayor and municipal building. The one in Viticura is an extraordinary modern structure on street bordering the most exquisite city park.

Everywhere you look there were places for people to picnic, play and just enjoy being outdoors. The ponds were full of swans and flamingos. And where else in the world might you see a Nespresso bar at a Sunday street market? In Vitacura, for sure.

We spent a couple of our days in the Santiago area in the city proper, another in Chilean wine country, and another up in the Andes in places that no other tourists seem to have found – thanks to Leo. But those are stories for another day!

…and if you have a few minutes and want to see a bit more…