This story is an excerpt from Ed’s book, A Casual Traveler

The ride from Santiago to Valparaiso was uneventful in comparison to some of my Asian bus adventures. I had planned to ride the Train del Vino while in Santiago, but it only ran on Saturdays. I arrived on a Monday, and didn’t want to stay in town that long.

 I’m a true wino at heart, and also planned on touring some Chilean wineries, but as fate would have it, I had to settle for doing my tasting in restaurants. To put it simply, I found Santiago was just too big and busy and noisy, and just not where I wanted to be at that point in my South American adventure.

Don’t get me wrong, I was impressed by the colonial architecture, and I know the city has many things to offer, but I just wasn’t in the big city mood. I needed something smaller, and more laid back. Valparaiso turned out to be just the place.

 On the bus, I sat beside a local guy, who appeared to be around my age. We struggled to communicate in broken English and Spanish. I gathered that he was retired from the Chilean navy, and proud of his prior service. He was married, with children, and he lived in Valparaiso.

He was curious about my plans and exact destination, but we couldn’t place it on the city map. He used his cell phone, and called someone to Google the street I was looking for. I had previously selected a couple of hotels, up in the hills above town, that were in my guidebook. The retired navy man seemed obliged to get me there. Silence eventually crept over both of us, and we nodded off for a bit.

 The city of Valparaiso took advantage of its position on the Pacific Ocean, by becoming a major shipping port. In it’s heyday, before the opening of the Panama Canal, it was an important stopover for ships on their way around the bottom tip of South America.

Logistics changed the shipping business after the Canal opened, but the city persevered. The port is home to several ships of the Chilean navy.

One of the attractions I was anxious to check out was the twelve old lifts, or funiculars, that carry you up the steep hills in the city. There were over a hundred of them at one time, but with the advent of the automobile, only a few are left and still in use. Time and progress changes everything.

On arrival in the city, I traded the bus for a taxi and headed into the hills, above the busy sea port. I hadn’t bothered to reserve a room, so I took a chance at having the taxi drop me out front of my first choice of hostels. It was full, but the helpful owner directed me to another place, just around the corner.

It was a warm sunny day, and I had no reason to fret, so I walked over to the place she suggested. The Allegretto B & B was a quaint looking place—an old Victorian style house, converted into a hotel. I thought I was out of luck once again, when I knocked and nobody answered, but then a head popped out of an upstairs window, and the man said he’d be right down.

He introduced himself as Ed, the owner of the place. He said he could give me a break on the room rate, since I was solo. The room looked adequate and the price was right, so I moved in.

Ed showed me the rest of the common area, that included a kitchen and living room, with seating areas. The decor was a mix of antique and eclectic, but so was the owner, Ed.

He was an ex-pat, from England, who’d fallen in love with a Chilean woman. He married her, and then relocated to be with her, and start a family.

After the marriage fell apart, the financial strain found him running a restaurant and the B & B to support his kids, and his new life.

Two things that caught my attention were quite unique for any type of hotel. There was a piano in the living area, and a huge coffee table, with an ongoing jigsaw puzzle—there for anyone who wanted to add a few pieces. Cool concept, I thought.

Ed was very helpful; he supplied me with a personalized local map, and list of things to see and do in the area. It was early afternoon, so I grabbed my camera and headed out on foot to check out the neighborhood and surrounding area.

First impressions tend to be lasting impressions. Initially, I was turned off by the amount of graffiti that was splashed on many  buildings. Then I realized there was something different about it, in Valparaiso.

There was the usual random tagging and ugly graffiti, but in contrast there was beautiful and colorful artwork—blended in. I headed down the hill towards the harbor. I was hypnotically drawn down strange alleys and staircases by the kaleidoscope of colorful and imaginative graffiti.

I saw eighteenth century architecture with contemporary artwork, painted on the facades. Was it contrast, or irony expressed by artistic graffiti?

Every building and block looked like a fresh canvas, painted by local and unknown, starving artists. There were painted cartoon characters and Jesus Christ himself. Another was a painting of the King, saying, Elvis is not dead. I saw new doorways leading to crumbling buildings, and shiny new cars parked in front of century old buildings.

There were stray dogs and cats lying in front of fancy doors to nightclubs. Colorful arrays of flowers spilled over old stone walls, but clumps of dog shit lay in the middle of the sidewalk—there was no grass anywhere. Exploring each block of Valparaiso was like reaching into Gump’s box of chocolates.

My wandering landed me at the foot of one of the working funiculars Valparaiso is famous for. They date from the eighteen hundreds, and were used to climb the city’s steep hills, before Henry Ford changed the world.

They are odd looking, but simple enough in concept. They are basically box cars on rails, with a motorized cable system that pulls them up, and eases them down the inclines. I don’t think any of the tracks I saw were more than a couple hundred yards in length, but the grades were very steep.

Walking into the ticket booth was like stepping back a hundred years in time. There was nothing automated—there were human ticket takers and change makers. The turn of the century machinery was still visible, and in good working order.

The interior of the conveyance was very plain, basically a wooden box car, with a couple of windows for ventilation and view, and wooden benches to sit on. With the number of tourists who ride the funiculars, you’d think they’d raise the fifty cent cost and use the proceeds to spruce them up a bit.

There were the usual tourist traps at the top of the run, but one particular hilltop patio caught my eye. It was a toasty day, so the vine and flower covered patio looked like a perfect beer stop. There was nobody else on the deck, so I had my pick of seats.

I perched myself near the railing, with a great view  overlooking the harbor. The contrasts of the city tickled my thoughts.

Beyond the old funicular was a completely mechanized shipping yard. Huge cranes moved containers from boat to land, stacking them four high. From my vantage point it looked like a living erector set, with trucks resembling dinky toys. The navy destroyers and frigates floated in the harbor like plastic toys in a bathtub.

I worked my way back down a different hill, purposely losing myself in the winding streets and alleys—musing at the new graffiti on the hundred year old brick walls. It was all so cleverly artistic, whether done purposely or not.

There were beat up brass and wood doors on a trendy new restaurant, fancy banks with marble facades, and grizzly old bums sleeping on the front stoops.

Even the squeegee kids displayed an artistic flair while soliciting funds in stopped traffic. These ingenious entrepreneurs had a timely act—one played a trumpet, while the other juggled three balls in front of stopped vehicles, waiting for the light to change. The real squeegee kids sat on the grass in the shade, perhaps awaiting their turn.

I did a loop through the rows of hawkers and peddlers, down at the pier, just in case something caught my eye. I’m not normally a souvenir shopper. I couldn’t help but notice some of the local street urchins, lurking under a huge shade tree. One gal had pink spiked hair, and so many tattoos it looked like her skin was blue.

A couple of the guys eyed me up; I could almost feel their hands grabbing for my wallet. What’s an inner city without scary looking people? The peddlers were not as pushy as in Asia or Mexico, where you’re constantly pestered.

I couldn’t pass up the smell of freshly made chorros and grabbed a bag. They are made from dough that has been pressed into a tubular shape, about the size of a sausage. Then they’re deep fried, and lastly, rolled in sugar. Basically, a sugar donut.

 I spotted another beer stop across the street from the pier, where some locals were whooping it up a bit. It looked like a perfect people watching spot, with a busy sidewalk. Unfortunately, the street was busy with lots of noisy and smelly diesel buses, that zoomed by on a regular basis.

The warm chorros and cold beer freakishly went together—just another contrast in Valparaiso. I can’t remember if it was the second or third beer, when I noticed the waitress was getting pretty friendly with me. She was a pleasant gal with a great smile, but her missing front tooth and belly bigger than mine, suggested it was time to move on.

 The evening found me searching for an upscale restaurant in my neighborhood. I had seen a place called, Pasta et Vino, in a couple of guide books. Apparently, it was a must do place, with a great wine list. It was only a couple blocks from my B & B, but for some reason, I couldn’t find it.

I stood at the intersection, where I thought it was supposed to be, with my head on a swivel. Usually, my nose for food steers me in the right direction. I could smell food, but couldn’t figure out where it was coming from.

There was a billboard on the sidewalk, just up the block from where I was standing. It was not the place I was looking for, but I stuck my head in the door, to be nosy. A young man intercepted me and introduced himself as the owner and chef. He said he would cook me anything that the other place offered.

I couldn’t find the other place, and I was hungry. Some times you just have to take a chance, so I followed him inside.      The restaurant was on the second floor, where I was greeted by a lovely young woman, who just happened to be the owner’s girlfriend.

There was nobody in the place, but I was early. I found that folks in South America don’t eat until after dark, sometimes as late as 11 pm. The room was lightly decorated; it looked fresh and new. The woman said they’d only been open about a month, and they didn’t have a menu yet. Weird, I thought.

They had a nice Chilean wine list. The chef came to my table and we talked about a customized meal, made to order, in consideration of my cravings and liking. We decided on a surf and turf meal, to be done in a mushroom cream sauce.

While I sampled and sipped a Chilean Cabernet Sauvignon, my appetizer was delivered by the missus. A plate of homemade crackers with a mayonnaise-based aioli dip. It was delicious. I chatted with the hostess while awaiting my main course.

The chef returned to my table and invited me into the kitchen, where we checked on my meal and sampled the mushroom sauce. I couldn’t identify one of the spices in it. He explained that it was Japanese in origin, and he bagged a sample of the stuff for me to take home.

The chef blew me away. It was the best meal of my whole trip.

For more stories from A Casual Traveler, see Ed’s Book Page