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Classic Santiago, Wines and Valparaíso

Get to know Santiago’s fascinating history, culture and scenery on a half day city tour of Santiago’s iconic sights. Escape to the colourful port city of Valparaiso which you’ll explore in the afternoon after a spot of wine tasting at the Casablanca Valley. This is the classic way to experience Santiago & Valparaiso and is one of our most popular trips. You can combine this with ‘Classics’ in other parts of Chile and Argentina to tailor your 2-3 week holiday.

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Classic Santiago, Wines and Valparaíso

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Trip type


Trip length

4 Days





Classic Santiago, Wines and Valparaíso - 4 Days - $1,374

Trip Summary and Itinerary Map

Day 1: Arrival in Santiago; Sensations City Tour; Hotel Singular

Day 2: Casablanca Valley & Valparaíso; Hotel Palacio Astoreca

Day 3: Valparaíso & Viña del Mar; Hotel Palacio Astoreca

Day 4: Transfer to Santiago International Airport

Start from Santiago and end at Santiago

Landmarks visited on Classic Santiago, Wines and Valparaíso

Operator's Itinerary

Day 1: Arrival in Santiago; Sensations City Tour; Hotel Singular

Upon arrival in Santiago, a private transfer and guide will be waiting for you at the airport to drive you to your hotel.

After a leisurely check-in you will enjoy a half-day private guided tour of Santiago, experiencing the city's diverse highlights with all your senses.

Visit the historic Santa Lucia Hill, in Barrio Bella Vista consisting of parkland, rising 69m above the surrounding areas and now adorned with ornate facades, stairways and fountains. It was on this hill that the city was founded in 1541.

Continue to the Paris-Londres neighbourhood, home to some of the most impressive colonial architecture before slowing down to briefly unwind with the locals and take in a curiosity unique to Santiago – coffee at one of the notorious and racy 'café con piernas'.

From there, you pass through some of the most interesting streets of the city, filled with history from the different waves of immigrants in this ethnically diverse city. Then wander around the art nouveau Mercado Central (Central Market), considered by National Geographic as one of the top ten food markets in the world and known for both its cuisine and exotic fish stores.

You will also visit the Vega Chica Market boasting some of the best flavours, scents and colours of this metropolis where you will try a traditional Chilean drink, the Cola de Mono.

The penultimate highlight is a walk through a renowned flower market filled with colourful displays and beautiful scents before ending your tour by exploring the lovely Lastarria neighbourhood.

Excursion: Half-day private guided tour

Accommodation: Hotel Singular, Santiago

Day 2: Casablanca Valley & Valparaíso; Hotel Palacio Astoreca

Today includes an exciting journey to Valparaíso, via wine tasting in the famous Casablanca Valley, renowned for its Chardonnays and Sauvignon Blancs, but also producing some lovely Pinot Noirs.

First of all, In the morning, you will travel through lush Curacavi Valley, known for its fruit farming and delightful restaurants offering traditional Chilean food. Continue into the Casablanca Valley, about 80km west of Santiago, where a winemaking revolution has positioned Casablanca as one of Chile's most important regions for the production of premium white wine. You will enjoy a tour and wine tasting at one of our favourite vineyards here.

After your wine experience you will drive on to Valparaíso, the oldest and most important port of Chile. This town's picturesque layout is enhanced by the surrounding hills that seem to dive into the ocean. Spend time with your guide walking through the city's winding streets and enjoying what once was the most important maritime destination of the Pacific coast before checking in to your wonderful, boutique hotel.

The location, views and charm of this renovated historic building makes for a truly memorable stay in this UNESCO-heritage part of town. You'll say goodbye to your guide as they'll return to Santiago this evening.

Excursion: Full-day private guided tour

Meals: Breakfast

Accommodation: Hotel Palacio Astoreca, Valparaíso

Day 3: Valparaíso & Viña del Mar; Hotel Palacio Astoreca

Today enjoy a wonderful, leisurely breakfast with views over the bay of Valparaíso, as you have the day to yourself to enjoy the region at your own pace. You might enjoy to base yourself at your hotel and enjoy the spa, or use the hotel's privileged location for wandering the colourful streets and alleys of Valparaíso, mingling with the street artists and perusing the many local handicraft stores.

Slightly further afield is the world-renowned Nobel Laureate Pablo Neruda's house, just 20mins walk away. Here you'll gain a fascinating insight into this colourful characater, one of Chile's most famous sons. Or you might prefer jumping in a taxi and heading to the nearby sophisticated Viña del Mar, possibly the country's most revered seaside resort, full of lush parks, beautiful avenues and an attractive promenade. This is a popular place for both Chileans and foreigners during the summer months from December to February.

Return from your activities this afternoon to once more relax at your stylish hotel and enjoy the magnificent views of the setting sun over Valparaíso.

Meals: Breakfast

Accommodation: Hotel Palacio Astoreca, Valparaiso

Day 4: Transfer to Santiago International Airport

Today, after breakfast, you will be transferred 1.5hrs by private vehicle (driver only) to Santiago International Airport for your onward flight.

Meals: Breakfast

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What our customers think of Classic Santiago, Wines and Valparaíso

Classic Santiago, Wines and Valparaíso trips scored 4.3/5 from 12 reviews

hiking on our own on a few of the torres del paine trails.

Travelled: January 2024

Isabel -

The whole trip was memorable so it is hard to pinpoint the most memorable. Generally the spectacular scenery.

Travelled: January 2024

Stephen -

Hiking to the Base of the Torres.

Travelled: December 2023

Beth -

There wasn't a "most memorable moment". It was an overall, ongoing fluid number of multiple moments. The trip was planned in such a way that we experienced the sheer vastness and beauty of nature for 7 days straight; landscape, animals, scenery, weather. The city visits (Valparaiso and Buenos Aires ) were guided in a way that we felt we understood all about each city's energy and culture. Having said all of the above, the providers at each piece of our trip were excellent! Above and beyond customer service was demonstrated in all avenues. My favorite place to be was Camp Patagonia! The food was 5 star.

Travelled: November 2023

Deb -

How can I answer this? The glaciers of Patagonia, Eco camp as a base for fantastic food, adventures and friends, the Ventus Australis for sophisticated exploration and great information ( as well as making new contacts), Puerta Varas for adventures and the best guides on the planet plus so much more.

Travelled: April 2023

Gina -

Experiencing the wild and rugged landscape of the Torres del Paine and El Chalten massifs. The dynamism of Patagonia will stick with me forever.

Travelled: March 2023

Megan -

Perito Moreno glacier is magestic

Travelled: March 2023

Paul -

Patagonia camp was absolutely sensational, the excursions and everything there was impeccable.

Travelled: January 2023

Henry -

Coming around the rocks at the end to see the twins! Breathtaking!

Travelled: November 2022

Anonymous -

First puma sighting!

Travelled: September 2022

Nikolas -

There were so many moments I look back on, but I guess one highlight was meeting with our guide Flo in the bar to discuss the adventure we just had and to plan the next day. Of course, a delicious Pisco Sour (or 2) was enjoyed during this time. The bar was buzzing with everyone else talking about their day as well! We would then move on to dinner with more laughs and stories of our day!

Travelled: April 2022

Betsy -

Whales feeding.

Travelled: January 2020

James -


Prices, Departures and Inclusions

The 2023/24 season price for two people sharing a room is USD $1,374 per person


Departures can be set up on a date of your choice, subject to availability.


Please get in touch to discuss your requirements.

Additional Notes

Accommodation – The accommodation in the itinerary can be modified if you wish. Please see our Santiago hotels guide for more information.


  • Meals: 3 breakfasts
  • Accommodation: 3 nights in hotels; 1 in Santiago, 2 in Valparaíso
  • Private airport transfers
  • Half-day private guided Santiago City Sensations Experience
  • Full-day private guided excursion to Valparaíso, via a winery in the Casablanca Valley


  • Meals not indicated in itinerary
  • Any extra/optional excursions
  • Personal equipment (see our recommended kit list)
  • Personal travel insurance
  • Gratuities/tips
  • International and domestic/in-country flights
  • Any visa, passport and vaccination expenses

Questions about this Trip?