Valpariso is Chile’s second city, and represents a small snapshot of the glory days of pre-Panama canal Pacific trade. Once one of the wealthiest cities in South America, there’s a real sense of a place who’s best days are behind it. I think that adds to it charm. Visiting Valparaiso is an easy 1½ hour bus ride from Santiago, and the slightly rough-around-the-edges port city makes an interesting contrast with the dull urban sprawl of the capital.

At first glance, it’s hard to get a sense of site. The lower town offers little other than claustrophobic but boring streets and too much traffic. The Plaza Sotomayor is a nice open space, and occasionally plays host to the pop-up markets that are common place in any urban centre in Chile. There are a few decent restaurants in this area serving some quality local seafood. But on first impression I found myself feeling a bit disappointed.

However, the real highlight of the town for was the upper town. A sprawling maze of stairs, twisting street and brightly coloured building, this is the real heart of the city. Maps are only of marginal use here, and it can be easy to get lost. It is quite an experience to wander down an nondescript looking alley only to find yourself at yet another stunning vista of the harbour. The vibrancy and colour is only added to by the graffiti. There’s a fun attitude to Valparaiso that I found so lacking in Santiago, and it's definitely the most accessible of the countries WHS.

While not part of the core zone, I would recommend taking the Ascensor Artilleria up to the Maritime Museum for a good view of the whole harbour. In general, the 15 or so funiculars are all fun in their own unique in their own ways. I really liked Ascensor Cordillera for its central location, and Ascensor Reina Victoria for its views.