I was looking for private tours around Valparaiso and was lucky enough to have stumbled upon Tours 4 Tips. They have tours at 10 AM and 3 PM everyday, except on January 1. Reservations are not required. Just look for the Wally (as in “Where is Wally?”) lookalikes.

They aren’t hard to find.
It was hardly a private tour. 30 of us turned up and they had to split the group into two, but the guides were pretty good with making sure no one was left out and that everyone in the group had the same experience.

Fernanda was an excellent guide.
They took us up Valparaiso’s hills…

On the Ascensor El Peral.
Down Valparaiso’s hills, via steep steps…

We heard a lot of stories about Valparaiso’s history, its struggles, and its people. We even got to meet one of its residents who offered us a special treat!

Don Sergio offered us a free sample of his “alfajores artesenales”. “Artesenales” is a word you’ll find above almost every shop and restaurant in Valparaiso.

Alfajores are chocolate-covered biscuit sandwiches, with manjar (dulce de leche) as the most commonly used filling. I returned and knocked on Don Sergio’s door the next day to buy five more at 200 Chilean pesos each (around US$0.34 or PHP15).
It was a great introduction to Valparaiso! Even Nicolas, who can’t stand group tours, enjoyed it.
The tours are about three hours long and end at a different point, all the way on the other side of Valparaiso, close to Pablo Neruda’s La Sebastiana home. Wear comfy shoes and bring a bottle of water. Suggested tip amount is anywhere from 5000 pesos (approximately US$8.50 or PHP370) to 10,000 pesos (US$17 or PHP745). Or if you think it sucked, you don’t have to give anything at all. But the guides are awesome and truly work hard for their money.
They also have two different tours in Santiago and I am tempted to do both at the end of our Chile trip.
Photos from our tour on 18 October 2014.