Take a look at the sidewalks. See the drop from the sidewalk into the street? If you stood in the extremely super narrow street, the sidewalk would come up to your shins, depending on how tall you are.
The city planners were actually quite thoughtful for pedestrians (or donkey owners).
Fun fact: The donkeys would walk in the street … and the human would walk alongside their donkey on the elevated sidewalk as to avoid stepping in the donkey’s poop.
Once you are up in the hills, Valparaiso changes from a gray port area into a very, very colorful city. There is street art almost everywhere you look. Graffiti artists would use anything as their canvas, like this:
But if you didn’t want your home to look like the above, you would give permission to an artist to use your home as a canvas. And then you might get something like this:
Or maybe something like this:
Our guide told us that a theory on why every home was a different color was to help sailors returning home, find their own home.
Perhaps you prefer pastels?
Or bright orange? 
Nothing was off-limits, not even the stairs:
And two of my favorite finds … (piano) stairs and (bubble) windows …
Valparaiso offers great exercise options — walking up and down the hills of the city.
There are plenty of trams transporting passengers up and down the hills.
From a construction standpoint, they are pretty incredible to look at. These photos don’t do them justice but they were built into the mountain so it’s a pretty steep ride up to the top.
Bonus: enjoying the views from the trams because you don’t need to pay close attention to walking … on steep streets with a lot of loose steps and stones.
A quick bus ride from Vina and I arrived in Valparaiso. Once in town, I made my way to a lovely hostel, that was more bed and breakfast than traditional hostel, at the summit of one of Valparaiso’s many hills (cerros).
I met two more travelers – Stephanie and Chris – and we chatted a bit until we realized we were hungry. Together we went to a nearby market to bring back some dinner – which, for me, was a personal-sized box of wine, cheese and crackers.
Before breakfast, I reserved my room for another night. At breakfast, I met Quinn and Joe, who, like me, had also left great jobs in NYC to travel. Over breakfast we realized we were planning to take the same walking tour. Together we headed out and it didn’t take long for me to fall in love with the city aptly nicknamed the ‘Jewel of the Pacific.’
Our free, organized walking tour started in Plaza Sotomayor in front of the Armada de Chile (Navy Building) and Monumento a Los Heroes (Heroes Monument).
Our guide started the tour with a brief history. We learned that neighboring Bolivia, now a landlocked country, once had access to the Pacific Ocean but during the War of the Pacific, Bolivia lost its access to the sea. Barricading Bolivia’s access has been detrimental to the country’s growth. This is still quite a big deal between citizens of both countries and there’s plenty online. More info can be found here and here.
Before the Panama Canal opened, Valparaiso’s port was an important stop for ships traveling around Cape Horn. Today, Valparaiso is a major seaport and shipping center in South America.
Speaking of major seaports and expansive shipping centers, our second stop: Valparaiso’s impressive port.
simply three cents 