After our swanky 3-winery tour in Chile’s Casablanca valley, it was time to explore the more eclectic port city of Valparaiso.  Valpo, as it’s called by locals, was once the busiest port in South America, until the construction of the Panama Canal eliminated the need for ships traveling from the Atlantic to the Pacific (and vice versa) via the Straights of Magellan to use it as a stopover point.

To get a good overview of Valpo before branching out on our own, we opted to take a walking tour with Tours4Tips Valparaiso.  So we made our way to Plaza Sotomayor to find “Wally.”  As the name – and the uniform – implies, we had to play a little “Where’s Wally” to locate our guide!

Despite being on the verge of losing his voice (a little too much partying last night, eh?), our guide Camilo didn’t disappoint.  Not only was he super-informative with a super-playful demeanor, his ‘stache was kick-ass!

A couple fun facts… Valpo has no official founding date.  There are 16 cities in world called Valparaiso.  This one was recently (in 2003) designated a UNESCO World Heritage Site.  Besides its historical importance as a major port, its claim to fame is its 45 cerros (hills) that rise up from the coast, forming a sort of natural amphitheater.  We started our tour by walking a block to the port where we could look inland and see the hills surrounding us.

It’s other claim to fame (though I’m not exactly sure that’s the word for it) is its graffiti.  So much graffiti.

In the flat area of town that sits on the seaside is where you’ll find the business district – government offices, commercial businesses, cafes, shops, etc.  The place is also covered in scrawl –  literally every single store front and façade had some sort of graffiti (surprising, considering its illegal).  And not the pretty mural-ey kind.  The ugly kind.  And far too much to constantly clean, so it’s sorta just been embraced as a characteristic feature of the city.

I have to admit, I wasn’t immediately impressed with Valparaiso.  Plaza Sotomayor was my first stop here and, although it had some nice elements, I didn’t find the majority of the surrounding architecture to be very picturesque (the graffiti, maybe?!?).  At least, not in the business district.  I knew there was more to it, though, and had high hopes for our next stop, nearby Plaza Anibal Pinto.  This, Camilo told us, was (unofficially) Valpo’s bohemian district.  It was a lively and eclectic neighborhood, with tons of locals out at the several bars and restaurants lining the square.

But as we walked along the street, I couldn’t get over all the trash I was sidestepping.  Not litter, but bags of trash waiting to be collected.  It was as though they were just tossed out the doors and stayed wherever they landed!  Trash on the street corners, trash lining the sidewalk.  Nothing to be ashamed of, according to Camilo, because garbage on the street is “the essence of Valparaiso.”

Uhhhhhhhhh, okayyyyy…. So, graffiti is a “characteristic feature” and garbage is “the essence” of Valpo. Way to try to spin it into a positive, Camilo!

After a couple blocks, we arrived at Ascensor Reina Victoria, one of Valpo’s famous ascensors (essentially outdoor elevators on tracks) that transport folks up and down the steep cerros.  At one time, about half of Vaplo’s hills had one of these funicular lifts, most of which were constructed in the late 1800s/early 1900s.  Today, only 8 are still in use and they’ve collectively been declared one of the world’s 100 most endangered historical treasures by the World Monuments Fund.

The tracks creaked and buckled (eek!) as Ascensor Reina Victoria carried us up a 52 degree slope (eek, again!) seven people at a time.  It could be a dizzying experience for someone afraid of both heights and enclosed spaces.  And anything old and wobbly, for that matter!  But at the top, 115 feet up from our starting point … Yesssss!  We were transported to a beautiful, quaint neighborhood, with several small B&Bs and modest restaurants tucked into winding stone streets overlooking the city below.  (We loved the look of Fauna Restaurant, so returned for an outstanding dinner with outstanding views after finishing the tour).

Yes, there was still graffiti.  But as unsightly as it was in the streets below, this was some of the most beautiful I’d ever seen.  The more appropriate term here would be street art – and it all had meaning.  Almost every mural had a story behind it and/or was painted in response to some social justice movement.  In the neighborhoods up here, much of the art is on people’s homes, but B&Bs, bars, and restaurants have also gotten in on the action and started commissioning pieces.  The area is so rich with murals/graffiti/whatever-you-wanna-call-it that Tours4Tips offers a guided tour devoted solely to Valpo’s street art and the local and national issues that inspired each work.

As we continued on, we passed by several understated churches and learned about the religious history of Valpo.  Catholicism used to be the only legal religion, so when the English and German migrants who settled in the early 1800s built Protestant churches, they left them unmarked (no crosses, no ornate architecture) so they weren’t obvious to authorities.  In 1865, a bill was passed making it legal to practice other religions; the churches have since been updated to reflect that they are, in fact, churches.

Our heads swirling with facts and dates, we needed a break to absorb it all.  So up a small sidewalk we went until we arrived at Don Sergio’s house.  Just a salty old local, selling homemade snacks from his front door.  There we sampled a truly delectable treat – alfajores!  He dips these caramel cookie sandwiches in chocolate, and they are freaking fantastic!  (That’s coming from someone who doesn’t like very many sweets.)  Our visit with Don Sergio, who also fed us the best empanadas I had during my whole 2-week visit in Chile, was my favorite part of the tour.

There were so many more special tidbits from this tour than I can possibly include in this already long post!  But after exploring the quaint, vibrant hills of Valpo, we ended our 2.5 mile walk back down at Plaza Sotomayor, at Tours4Tips’ office in a hundred-year-old home adjacent to the square.  There, Camilo offered us one last treat – Chicha!  An apparently famous Chilean cocktail, it’s Chichon for those who prefer formality (and raise their pinkies when they drink!).  Great end to a great tour, and the perfect send-off before venturing out to enjoy some Valpo nightlife.

If you go

Tours4Tips Valparaiso, as the name implies, offers free tours; the guides just work for tips!  They offer several walking tours, but ours was the Valparaiso Highlights Walk, a 3-hour tour that leaves from Plaza Sotomayor daily at 3pm.  You can get to the Plaza by taxi, bus or car (we had a rental, and used the public parking deck just adjacent to the plaza … you’ll see cars parked in the plaza, but don’t do it or you’ll get ticketed!).

It’s a great way to get an overview of the city before diving into some more in-depth exploring on your own.  In fact, tell the guide your interests, and he/she will give you plenty of recommendations for additional sightseeing and activities.  I highly recommend this tour (and Camilo!). Enjoy!

Not staying in Valpo? No worries, you can still check out the street art on a day trip from Santiago! Check out how my friend Kelly did it.

[mc4wp_form id=”905″]