We booked a tour that would take us to the cruise ship in San Antonio via Valparaiso and neighboring Vina Del Mar (for about the same price as a transfer to the boat). In picking up the other passengers for the excursion, we got a tour of the downtown area, where most of the stores are closed and boarded up, graffiti covers everything, and even traffic lights have been destroyed, making navigating intersections without traffic cops challenging. The entire downtown area is lined with barricades and we saw lines of paint splattered armored vehicles.
Outside of Santiago, we drove through the Casablanca Valley. The countryside is very dry, river beds are dry, and we saw evidence of recent fires that are whipped up by high winds. We stopped at a winery that had been covered in corrugated steel to protect it from protesters who were traveling by bus to protest in Valparaiso.
We saw lots of people walking along the highway with backpacks. It turns out they are pilgrims heading to celebrate the feast of the Immaculate Conception on 12/8, the largest religious festival in Chile. The day before the festival, the highway will be shut down to accommodate over a million pilgrims making their way to the monastery perhaps 40 miles outside of Santiago.
Valparaiso was once the busiest port in Chile before the Panama Canal opened ( when ships had to go around Cape Horn to transit from the Pacific to the Atlantic). It’s a beautifully old city, a UNESCO World Heritage site, but unfortunately marred by graffiti and protests ( since the Congress is in Valparaiso).
The steep roads up the hills of Valparaiso are full of colorful street art.
We visited Pablo Neruda’s house overlooking the port.
Many of the lovely old homes have been turned into hotels or museums.
We also rode the Cerro Alegre Valparaiso funicular.
Next we visited Plaza S0t0mayor with its Wedgwood naval building and its new building built inside of the old. 
Right next door to Valparaiso is Vina Del Mar, the newer, wealthier city.
Vina del Mar Flower Clock with workers trying to remove graffiti from a recent demonstration.
In Vina Del Mar, we saw one of the Easter Island moats donated by the Rapanui people to the city.
On the way to the boat in the port of San Antonio ( cruise ships moved to the new port after union protests shut the Valparaiso port several years ago), we stopped at The Indomita winery in the Casablanca Valley, the Chilean capital for cold climate white wines.