Chile’s capital is easy to navigate, full of delicious food, and makes a great base for day trips. Three days is just enough to sample the city, sip some wine, and visit the coast. We mixed urban exploration, a private wine tour, and a bus ride to Valparaíso for a well-rounded experience. Here’s exactly how we structured our trip to Santiago, what we loved, what we’d do again, and some practical tips we learned along the way.
Where to Stay: Best Hotels for Every Budget
We based ourselves in Las Condes, one of Santiago’s most polished neighborhoods. It’s safe, has plenty of restaurants and cafes, and is well-connected by metro and Uber.
- Splurge: W Santiago. We were on a tighter budget this trip, so we didn’t stay here. We did spend some time on the rooftop and at its lovely restaurant Karai (more on that later). We highly recommend staying here if you can squeeze it in the budget, but we also have two other great recommendations below.
- Midrange: DoubleTree by Hilton. This is where we stayed. We got our room on points, so it was free and in walking distance to the W and lots of great restaurants. It was clean, reliable, and centrally located, with great breakfast and dinner options.
- Budget/Points: Hyatt Centric. We almost booked this for only 8,000 Hyatt points per night, but we wanted to be in walking distance to check out the W. While we didn’t stay here, it’s definitely on our list for a budget-friendly stay on a future trip.
Pro Tip: Uber and the metro are very convenient around the city, so you don’t need to be in the center to get around easily.
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Day 1: Exploring Santiago’s Top Markets and Attractions
Morning: Markets and Local Food
We started at the best market in Santiago, Vega Central, a massive local produce market. It’s loud, busy, and authentic. You’ll see everything from giant avocados (paltas) to whole fish, and plenty of vendors moving about. Grab a fresh juice or just wander. Be aware: it’s a working market, so expect a bit of chaos, but we were so impressed. There are also little restaurants all around if you’re ready for a meal, and you can check out Vega Chica next door.
From there, we walked to Mercado Central, which focuses more on seafood and dining. We sat at a casual stall and had a local beer in between stops. This market is more touristy but still worth a visit.
Make sure you try a completo, Chile’s version of a hot dog. It’s topped with avocado, chopped tomato, mayo, and often sauerkraut or onions. It’s a classic street food you’ll see everywhere.
Midday: Historic Center and Museums
Next stop was Plaza de Armas, the city’s main square and historic heart. You’ll see the Metropolitan Cathedral, old government buildings, and lots of street performers and vendors. It’s a good place to sit on a bench, people-watch, and take a short break.
From there, we walked to the Museo Nacional de Bellas Artes. It’s free to enter and has a solid collection of Chilean and Latin American art. Even if you’re not an art person, it’s a good indoor stop with clean bathrooms and AC (if visiting during warm months).
Afternoon: Bellavista + San Cristóbal Hill
In the afternoon, we explored Barrio Bellavista, a colorful, artsy neighborhood known for its street art, boutiques, and small restaurants. It’s a great area to wander without a plan.
We took the funicular up Cerro San Cristóbal, one of the best city viewpoints. You’ll get sweeping views of Santiago with the Andes in the background (if the weather cooperates). There’s a small café at the top, but it’s mostly about the views.
Evening: Rooftop Drinks and Dinner at W Santiago
We took an uber back to the W and headed to Red2One, their trendy rooftop bar with gorgeous views of the Andes. The cocktails aren’t cheap, but this is one of the best sunset spots in the city. We got there a little before sunset to grab a good table and have an espresso martini before dinner. If you’re not staying at the W, you can still go, but check their hours and consider making a reservation. We had to talk our way in before a private event. They let us up for a drink 30-minutes before our dinner reservation in the hotel at Karai.
Karai is the W’s in-house Nikkei (Peruvian-Japanese fusion) restaurant. The dishes were beautifully plated and flavorful. The restaurant had great ambiance, and the staff were amazing. We let our server curate a meal for us, and everything was perfect.
Day 2: Wine Tasting in Casablanca Valley
This was one of our favorite days of the trip. We booked a private full-day Casablanca Valley Wine Tour through Viator. The driver picked us up at our hotel in the morning, and we spent the day exploring three different vineyards.
Stop 1: Viñamar de Casablanca
Our first stop was Viñamar, known for its sparkling wine and beautiful setting. We sat on the terrace with a cheese and fruit platter (not included in the tour price but affordable) and started the journey right with bubbly and beautiful vineyard views.
Stop 2: Viña William Cole
This is where we had a full tour of the production area and an included tasting of their whites and reds. This was a more educational stop with a knowledgeable guide walking us through the winemaking process. It was a very laid-back and peaceful stop.
Stop 3: Casas del Bosque
We ended the day at Casas del Bosque, one of the more well-known wineries in the area. This stop was crowded with wine enthusiasts from many different tours, but the vineyard setting was beautiful, and the food was delicious. Lunch here wasn’t included in the tour, but it was reasonable. We ordered the 6-course tasting menu with wine pairings, which was a lot of food and wine (but it was also a late lunch at 3:00 PM). At the end of the experience, we were happy and ready to nap on the ride home.
Back to Santiago
We had done enough imbibing on our Casablanca wine tour to need a nap when we got back. Then we had a light dinner at the DoubleTree restaurant, which was actually pretty good. We got to sit outside on the terrace and people watch.
Day 3: Day Trip to Valparaíso
On your final day, we recommend taking a day trip to Valparaíso, a colorful port city about two hours away. You can drive, book a private tour, or take the bus.
We went with Flixbus, which was cheap, comfortable, and on time. It was $25 round trip for a couple, including seat selection. Buses leave frequently from the main station in Santiago (Pajaritos)and drop you not far from the Valparaíso center (but you’ll need an Uber to get you all the way there). You can book Flixbus online in advance and select a seat.
We read some complaints about the Valparaíso bus station, but it was clean and felt safe when we were there. As always, take safety precautions, be aware of your surroundings, and try to travel during daylight.
Note: We actually spent two nights in Valparaiso, and recommend at least an overnight excursion, but this is totally doable on a day trip from Santiago, and you don’t want to miss it!)
On Arrival in Valparaíso: Cerro Alegre + Street Art
Once in Valparaíso, we focused on the Cerro Alegre and Cerro Concepción neighborhoods. These are the most walkable parts of the city, full of vibrant murals, steep staircases, and funiculars. Just wandering the streets here is the main attraction. Bring good walking shoes and be ready for steep hills!
You can also visit La Sebastiana, one of Pablo Neruda’s homes. It’s set up as a museum and worth a visit if you’re interested in his life or want a great view. Valparaíso is all about the views and street art.
Lunch with a View
For lunch, check out Hotel Boutique 17 (which is where we stayed). The have a very small lobby, but their patio restaurant downstairs has stunning views and is a perfect spot to soak in the beauty of Valparaíso. You could also check out Restaurant La Concepción next door.
Evening: Return to Santiago
If you’re visiting on a day trip, we would recommend giving yourself about 4-4.5 hours in town on your Valparaíso day trip. You’ll need to get an Uber over to the center. You’ll want to walk around a bit, enjoy a slow lunch, and then hop back over to the bus station to get the Flixbus back. Maybe take a 9:00 AM bus departing Santiago, and the 3:15 PM bus back.
We also took the train up to Viña del Mar, a neighboring beach town, but didn’t really get the vibe. So, we would skip it if we did it over.
Travel Tips
- Getting around: Uber is cheap and reliable in Santiago. Metro is easy too, but we mostly used Uber for convenience.
- Wine day: Our private tour included one tasting and all transport. The first stop’s wine/cheese platter and lunch at Casas del Bosque were extra but not overpriced.
- Weather: Santiago can get hot in summer and chilly at night. Bring layers and don’t forget the sunscreen.
- Cash: Most places accept cards, but some street vendors and markets are cash only.
- Language: A little Spanish goes a long way. Most tour guides speak English, but it’s not spoken very widely, even at restaurants or hotels. We love this because it gives us a chance to improve our Spanish skills. You don’t have to be fluent by any means, but practice a few words and be prepared to translate.
- Tours: If you don’t speak any Spanish, you may want to build more day tours into schedule with groups like WithLocals or things you can find on Viator.
With three days in Santiago, you get a solid intro to Chile, but you’ll also want to branch out to see Patagonia, the Lake District, the Atacama Desert and all the magic of this beautiful country. Let us know if you’ve been or if you have questions about planning a similar trip!
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