We spent one of our precious few days in Santiago exploring a little of the surrounding area, so we grabbed a friend of mine who happened to be in Santiago at the same time, hired ourselves a driver/guide (the most excellent Gonzalo from Experiences_Santiago) and went out to see a little more of Chile. First stop on the 100 mile journey to Valparaiso was Veramonte winery in the Casablanca valley. A bio-dynamic and sustainable vineyard, we were treated to a very low key tour and fantastic wine tasting/nibbles. They even had fresh-pressed orange juice and muffins for my kids, along with a colored pencils and a tote bag, so, as far as snooty vineyards go, this is one of the better experiences I have had- the coastal mountain range covered with sweeping vine trellises makes for a striking view whilst imbibing.
Whereas Santiago felt like LA, Valparaiso ("Valpo" to the locals- and to me, a regular cool guy) feels very reminiscent of San Francisco- in fact, American sailors in the 1800s actually referred to Valpo as "Francis" as they were humoured by the similarities between the two, ahem, bohemian cities. A city known for how "the hills slide into the sea" (at least 42 hills, in fact). The city was officially founded by the Spanish in the mid-16th century, was raided by Sir Francis Drake himself on more than one occasion (taking Peruvian gold bound for Spain), as well as featuring prominently in several naval Battles between the US and England during the war of 1812, Valparaiso is one of the many port towns that lost much of its luster due to the Panama Canal being finished in 1914 and the slow trickle of people moving to Santiago (100 miles SE). Despite this, Valparaiso is still the third largest Chilean city, with the population of the greater area approaching 1.8 million. The city boasts a host of treasures, related to both the food and street art found easily throughout the city.
One day in Valparaiso is enough for anyone to generate strong feelings about this charming seaside town. Outside of Buenos Aires and Rio de Janeiro, this is probably the favorite city that I've travelled to in South America. Colorful, arty, brilliant seafood, historic buildings and a picturesque view make this a can't-miss Chilean experience.