We were up and at ’em rather early on Monday; road trip #2 had us headed westwards towards the ocean. Everyone was rested and excited to go to a beach, though please let the record state that I’d provided ample forewarning that the beaches at Valparaiso and Vina del Mar were not going to be like the beaches our little people absolutely adore.

The Chileans–being exceptional miners and all–wholeheartedly believe going through a mountain is easier than going around it (or over it). The drive to Valparaiso is a short, pretty one that ambles across the Casablanca wine country (which we sadly saw only from the highway) and through several, lengthy mountain tunnels. Roughly 90 minutes after we left our apartment, we pulled into the parking garage where we were to meet our tour guide, Michael the German Pirate.

(Thank goodness Russ insisted on a tour guide; we’d have never, ever figured out Valpo otherwise.)

Before I go any further, I want to shout from the rooftops that Michael was an excellent choice for a guide. He replied to my initial email in a matter of minutes, spoke fluent English, and was more than happy to accommodate some surly teenagers.

Valparaiso was once a very weathy shipping town and layover point for folks making the insanely long and hard journey from Europe around Cape Horn. Then a little thing came along called an earthquake (in 1906) and another little thing came along called the Panama Canal (in 1914), and poor Valpo lost its footing as a South American metropolis.

In keeping with Chilean geography in general, Valparaiso is incredibly unique. Tall, tall cliffs drop straight down to the sea. To help with getting up and down these gigantic hills, the city built a system of funiculars–many of which are still in use 100 years later. Its buildings and alleyways are covered with murals painted by some pretty talented folks. All of these factors have helped Valparaiso be declared a UNESCO World Heritage Site, something the city takes very seriously; roughly only 1,000 sites on the entire planet have earned UNESCO World Heritage status.

After giving us a quick peek of the city from the top of the parking garage, Michael then took us across town on the antiquated trolleybus–actually a Chilean national monument–where we got our first taste of Valpo’s infamous street art.

The work above, Solsticio de Invierno, was created by UnKolorDistinto, a couple who is regularly commissioned to design and paint various public art murals.

Street art is the name of the game in Valparaiso, and almost all of it is pretty spectacular, particularly when given the grand scale of it.

Michael took us by one of Valpo’s most popular places for chorrillana (Casino Social J. Cruz –one of the greatest named places ever) , which is a carboholic’s dream of a dish composed of french fries covered with some type of meat, onions, cheese, and a fried egg. Michael is not a fan, and I can’t say I blame him after seeing a few plates piled sky-high go passing by. While we didn’t eat there, it was still a great stop on the tour because the place doubles as a knick-knack hoarder’s wildest dream. (Side note: J. Cruz completely reminded Russ and me of another bizarre place: Takatakata–hands down, the dive-iest dive bar on the planet–which we managed to visit and live to tell about. It’s located in Buzios, Brazil. Tell Kaiser you heard about his place from me. And watch out for the machete.)

Time for a funicular. We rode the Reina Victoria up to the top of Cerro Concepcion and started our search for a lunch place without felines prowling around inside of it.

On the way to lunch, Michael told us about an unbelievable mountain bike race–the Cerro Abajo–that takes place annually in Valparaiso. Racers plummet from the highest point in Valpo all the way down to the sea, lacing through narrow pathways and staircases and concluding by going through a building and jumping over an entire street. Of course the boys were immediately asking for the wi-fi password at lunch in order to track down a video of it. It’s utter insanity; consider yourselves forewarned!

After lunch, it was time for even more street art!

Finally on to Cerro Alegre! This one above, created by Art+Believe, is synonymous with Valpo; here’s a cool montage of its creation.

Next up, the equally as well-recognized Piano Stairs.

Sensing one of his day’s clients had likely had enough street art and was a much more business-minded individual, Michael managed to sneak us in to the Bolsa de Valores–the (sadly, now shuttered) first (and busiest) stock exchange in Latin America. The trading floor was eerie in its silence…and beautiful in its architecture.

We were all definitely hitting the wall at this point, so we asked Michael if he wouldn’t mind getting us on to the thing Tucker had been asking about since we’d gotten up that morning: the beach.

He suggested we all load up in our rental car (Russ driving, Michael in the passenger seat, and the three boys and me all crammed in the back–not the safest way to travel) and head down the road the six miles or so to Vina del Mar.

Of course, the ocean was freezing, but that didn’t stop Tucker from going all the way under–a decision that made for a long car ride back to Santiago for him.

We rolled back in to Santiago tired, dusty, and hungry and not willing to venture out for a proper dinner…again. After a battle royale over where to eat, we basically all pouted through the meal and then hit up the Jumbo grocery store for some provisions before heading home and to bed. We had just one last road trip ahead of us.