It was only day two and I lost my debit card.

But it was a funny situation that involved  a crazy British driver, a two-day pilgrimage that closed a major highway, and a wine tasting that needed our prompt arrival by 10:30 in the morning.  So, no debit card and a volume of funny moments that ensued made day two fabulous anyway.

We were on our way to wander the winding staircases and cobbled streets of Valparaiso and I was excited.  I read about the pre-earthquake roaring times of this maritime city, and I was looking forward to seeing its reputation for funk and charm in action.  Dominic, my Airbnb host and driver companion for the day, reminded me of how Valparaiso lost its Pacific Ocean verve after the Panama Canal opening, since ships were less likely to pass through Valparaiso with the increased ease of direct navigation through the isthmus.  That sense of a past “hey day” was palpable at the bottom of the hills, with dilapidated buildings in every block, and a general sense of outdated infrastructure.  With that said, I noted a few remnants of historical architecture that survived the two most recent earthquakes in Chile.  Beautiful buildings.  And the hillsides of the city, two specifically that are UNESCO World Heritage sites, represent the city’s signature and for which Valparaiso is most known.

One of Valparaiso’s most notable characteristics was its dramatic and prolific street art.  Sides of buildings, street walls, banisters, wherever there were blank surfaces there were creative murals and beautiful faces found.  Punchy, bold colors in all directions, unapologetic and amazing.  I wondered where this talent was developed, at what age, if there were graffiti artists and gangs the way there were in San Francisco.  I felt good being in a place where public, free art was a daily given.

Another note about this city was it’s neighborhood ambience.  I had some time to myself and I found a corner of an outside patio to eat lunch, read my book and look ahead to my southern wander to Pucon the next day.  A woman with a warm smile and a directive energy greeted me (I assumed she was the restaurant owner), and a man with two dogs arrived at the restaurant when I did, and he took over the neighboring table.  A third dog followed (either owned by the man or as a buddy to the two dogs, I’m not sure).  The owner and the man started catching up in their clipped, musical Chilean Spanish with the two dogs under their table, while the third dog patiently sat by my side waiting for a food reward from me.  A man across the street in a bright yellow vest, which could have been suited for a construction zone or street crossing of little kids, starting singing opera.  He had a wonderful voice.  His singing caught my ear as he leaned over the fence of the patio, chimed into the chat with the owner and the man briefly.  The dogs didn’t make a move, this scene was typical.  The opera singer excused himself, singing on his way out of the conversation, and the original duet carried on.  This was all located immediately next to the Valparaiso School of Music, and there must have been a bell choir rehearsal happening at this time as well.  I was on the set of a Chilean musical for those few moments, with a hint of winter holiday flavor as the background score.

This day closed with a hairy set of logistics that included illegally parking Dominic’s car a hairline’s distance from where the buses pulled out of the bus station.  Due to the pilgrimage, which would last two days, we took a longer route back to Santiago, up through Vina Del Mar and then eastward, with a snooze en route.  The late afternoon isn’t worth writing the details, all of them are funny and/or absurd, and all of them hallmarks to a last-minute road trip in a new place.