Valparaíso sits only an hour and a half away from Santiago’s city center. It’s a pretty easy drive out there, you’ll just need to follow the main signs from Route 5 to Route 68, where two tolls (2700 CLP each), a couple long tunnels, and beautiful wine country comprise your commute.
In my limited experience, the areas immediately surrounding port cities can be a little grimy and Valparaíso certainly conforms to this theory. Stray dogs abound (similar to Santiago), but so does their stray poop on almost every sidewalk and walkway (not so much in Santiago). It can be hard to avoid since there are so many, many murals and beautiful vistas of the city—trust me on that one!
Prat Wharf is just beside the plaza, both a tourist attraction and launch pad. Tourists wait for small dinghies to take them around the bay and plenty of South American cruises start or dock here. Street vendors sell churros, popcorn, jewelry, keychains and other souvenir knick-knacks. There looked to be a shopping center adjacent to the port as well, but we only entered in order to use the bathroom (250 CLP each). 
You can find parking under Plaza Sotomayor, the main plaza in Valparaíso. Rates are by the hour, but the daily max is 10,000 CLP. It certainly beats trying to find street parking and you can avoid driving on the steep San Francisco-esque hills (driving here may even be more extreme than SF because of all the curves and tiny streets!).
Government/civic buildings and coffee shops surround the plaza. A statue dedicated to the Heroes of Iquique (sailors who lost their lives during the Battle of Iquique on May 21, 1879) sits in the plaza center.
Watch out for cars since streets run directly through the plaza and there’s not much visual demarcation to differentiate the street from pedestrian walkways. Many tourist guides I read recommended the Tours for Tips 3 hour walking tour (pay only the tip you’d like to offer), which starts here at 10am or 3pm, but we went along on our own instead. I’ll never know exactly what we missed, but it seems like much of Valparaíso’s charm is getting lost in the curving streets of the hills and discovering street art along the way.
The lady we paid for the bathroom and someone from the naval building were able to point us to the right bus line to take up to La Sebastiana, Pablo Neruda’s house. The O Line microbus has a local fare of 280 (tell the bus driver “un local” for 1 local fare) and dropped us off 1 block from the entrance to the Pablo Neruda house museum, saving us from more than a few strenuous hills. The high school next door is also named after Neruda.
I think visiting La Sebastiana has been one of my favorite activities in Chile so far. Honestly, if you can only do one thing while in Valparaíso, touring La Sebastiana should be it—I’ve written all about our experience touring it in another post.
Right beside La Sebastiana is a small café serving coffees, teas, but not much in the way of a full meal. The souvenir shop sells prints of Neruda’s poems with complimentary artwork on posters, magnets, postcards, as well as items that recall his Valparaíso house (wine glasses with blue stems, replicas of his punch bowl cow). Down a short pathway is a poetry library for locals that doubles as a tourist center.
Walking down from Cerro Bellavista offered beautiful views as the name suggests. Artisan ware, along with regular tourist souvenirs lined Paseo Ferrari. There were monuments to poetry and the arts all around. Just one block down from La Sebastiana, past the artisan stalls, sits a park dedicated to the poets.
Arts abound in Valparaíso. If it wasn’t enough to have monuments to poetry, or street art and murals galore, the very streets and buildings of the city are entrenched in arts. We saw teenagers all over town with scratch pads and ink, sketching various scenic views or interesting buildings—there were so many, I wonder if they weren’t all students on a Sunday afternoon assignment.
Valparaíso has so many hills, it’s made their hill elevator system famous (ascensores, or funicular in English, as I learned). They’re scattered about the city, rickety and old, but most are still functional. For as little as 100 pesos, you can take a ride up a hillside (Click on this link to download a 10 sec video of the inside of an ascensor as it lifts). Trying to get the video of the view of the ocean to load. It’s currently being fickle =(
The town reminds me of Costa del Sol in Spain . Great memories and wonderful times
Yes, just with much more color and less beach! Viña del mar is the local beach town, about 15-20 minutes up the coast from Valparaíso.
I looked at a map of Chile and discovered there are two towns with that name in Chile. The other is farther south. In looking I noticed a town called Los Angeles, Chile. Are you going there? You could tell them you grew up in Los Angeles! They might think you have a funny accent though….
We went to the one closest to Santiago! Haha, no Los Angeles in Chile for us. Although another awesome place on the map is called “Lolol” – made me want to laugh out loud!