February 2025

Day 1

We arrived to Santiago mid February and were met with 90 degrees heat, a nice change from freezing New York. Santiago is a big city with bustling pedestrian center that is mainly a giant indoor and outdoor shopping mall.

Since we didn’t have a local sim yet we got an airport taxi which was only slightly more expensive then Uber to go to our hotel that was right in the center of old town/downtown and after a 2 hour nap went on to explore the city. Uber is readily availble in Chile and is not expensive.

First we took a free walking tour with Petro; frankly I didn’t know much about Chilean history so the tour was very useful and enlightening. In the afternoon we had coffee in café Bombei which is a type of a coffee shop called “cafe with legs”. This is a unique phenomenon typical to Santiago. When you get there you are not sure if this is a café or an escort service. All the waitresses are wearing extremely revealing outfits; low cleavages, very short skirts or dresses and very high heels.  The girls are sitting and talking with the customers who are mainly middle aged males. We heard about those places and were curious to see it. Surprisingly, the coffee was really good and they had internet!

In the evening we went to Lestaria, a neighborhood full of restaurants, a walking distance to downtown. We had dinner in Mulato restaurant. Good ceviche and ok fish. Ceviche is a very popular dish in Chile and pisco sour is the drink to have. Afterwards we crossed the river to Belavista, a neighborhood full of nightclubs and bars with music and lots of drag shows.

Day 2

The next day we took the metro (easy to navigate) and went to the Memorial for Human Rights. It’s an amazing museum showing how the country slid into dictatorship and climbed back out. There is an abundance of videos and documents from eye witnesses and the victims of the Pinochet era regime; highly recommended.

After the museum we took a free walking tour of the Yungay neighborhood in which the museum is located. Yungay is very quiet and colorful neighborhood and apparently this is where the President of Chile lives and we got to see his house.

Also in Yungay is the French barber shop and restaurant, the oldest barber shop in South America. https://peluqueriafrancesa.com/.  We couldn’t miss the opportunity; bf got a haircut while we were sipping amazing pisco sours. Another notable place in Yungay is Espacio Gargola, https://lagargola.cl/ a very interesting building and also a restaurant good for lunch.

In the evening we went to Don Rodrigo, a hotel bar with live music located in Lestaria and continued to more night life in Belavista and ended up in a drag bar called Narcissis.

Day 3

We rented a car thru carrentals.com ($80/day) and drove east. What was supposed to be a very short drive turned out to be painfully slow and long due to road construction, detours, confusing signs and Saturday traffic.

Our plan was to do wine tasting in several wineries in Casablanca Valley but because we got there much later than planned we could visit only two wineries. The first was very posh Casas del Bosque. The setting is very impressive no less then upscale wineries in Napa valley or Tuscany.  Instead of a full tour and tasting ($25 pp, 4 wines no snacks) we opted to lounge in the garden under an umbrella and ordered couple of different whites from the menu together with a nice charcuterie plate.  Chile in general has good Sauvignion Blancs and we were not disappointed. The restaurant looked very good but again we were late and couldn’t be seated.

The second winery we went to was Bodegas RE, also nice but much smaller tasting room. It is possible to do a full tasting with or without a meal or just order a glass at the bar. At this point it was already late in the afternoon so we had to leave the valley to drive to Vina del Mar, our night stop. Overall, we felt that we under-explored the Casablanca Valley and may return in the future for a few days long tasting trip.

In Vina del Mar we stayed in hotel Pullman mainly because they have a pool and I was planning for half day at the pool but the weather changed suddenly and it became very cold. We were told that this happens often due to specific micro climate in the area, therefore I wouldn’t recommend this place as a beach vacation.

Otherwise, Vina del Mar, which is a summer place for many Chileans I (I guess they don’t mind weather changes) is a very busy coastal town. The beaches stretch north for many miles and become different towns. The main street is full of mid range and chain restaurants. We were hungry and had dinner at some random parilla after which we went to look for evening entertainment. Most bars have karaoke which is extremely popular with Chileans and we also managed to find one bar with a rock band. Since this is a resort town most places are open very late.

Day 4

Our next destination was the famous town of Valparaiso. I read that it’s not a very safe town and that we shouldn’t park on a street there so we decided to take an Uber and left the car at the hotel. When we got there the town looked very unappealing, dirty, grey and sad. I was not sure why it was even recommended. But I already booked a free walking tour so we decided to stay. After having the biggest empanadas I ever seen our mood improved.  I must say that it was definitely worthwhile to stay. Our guide, who looked a little bit like count Dracula, all in black and sharp teeth, took us up to the upper levels of Valparaiso which turned out to be lively and fun with lots of stores, cafes, bars and street musicians; with lots of people strolling around. The views from the upper town are great as well.  The guide was knowledgeable and a good storyteller; the tour was good and very long, about 4 hours. After the tour we ate dinner in Restaurant Capri recommended by our guide; simple local food, not gourmet but fresh tasty and inexpensive. This was a very full day so we skipped the night entertainment.

Day 5

On our last day was back in Santiago and we went to San Cristobal Hill and rode the cable car up and down the top. It is also possible to take a tram in one of the directions and/or hike. The views are amazing; the park is very large and one can spend several hours there. Unfortunately we didn’t have that much time so we continued to have lunch at the famous Santiago city market.  The market is famous mainly for numerous seafood restaurants. The moment you walk in you get crowded by the waiters/owners of various restaurants all trying to persuade you to eat at their place. We chose one that offered a good deal on the crab with full meal, sides, wine and even pisco sour.

For afternoon coffee we wanted to visit another “cafe with legs” but couldn’t find the one that we wanted.  An elderly man who saw us looking at the map struck a conversation with us and pointed us to a building directing us to take an escalator to underground floor where he said there are many places of that sort. This turned out to be quite an experience. The whole floor had maybe 30 places all called by various names with a “Café” attached to the name. They all looked like strip joints. All very seedy, doors closed; windows tinted and when we walked in we were met by barely dressed women offering… coffee.. We didn’t stay as this was a little over the top weird and had coffee elsewhere.  

Feeling totally satisfied and most of the plans accomplished we proceeded to the airport.