Countryside, Culture & Coast Trip Highlights

  • Discover Santiago
  • Vineyard visits and tastings
  • Pacific Coast and Valparaiso

Itinerary Overview

Come see the many faces of central Chile. Explore Chile’s vibrant capital city Santiago and feel the pulse of the country. Enjoy a sunset wine and cheese tasting after a horseback ride through Viu Manent vineyard. Meander the bohemian, colonial port city of Valparaiso discovering one of South America’s most vibrant arts and culinary scenes. Relax on black sand beaches in a sleepy Pacific Coast fishing village. Visit the home and curious collections of Chile’s Nobel Prize-winning poet Pablo Neruda.

Chile highlights


Meet in Santiago. Relax before visiting La Moneda Presidential Palace, Santiago’s bustling pedestrian malls, Santa Lucia Hill and the nearby artisans market.


Discover more of the city by bicycling through the bohemian Bella Vista neighborhood, the Central Market and the Plaza de Armas. Afterwards, set out for the vineyards of Colchagua Valley.


Visit the Colchagua Museum and the town’s central plaza before a tour and wine tasting at renowned Montes Vineyard. Enjoy a Chilean asado (barbeque) for lunch, followed by a gentle horseback ride through the Viu Manent vineyard with wine and cheese at sunset.


A scenic drive takes you to the seaside village of Matanzas. Stroll black sand beaches and watch the waves while in a wood-burning hot tub.


Explore Matanzas, meeting local fishermen and villagers. Visit Isla Negra, the peculiar former house of Nobel-winning poet Pablo Neruda before arriving to Valparaiso.
*Optional windsurfing or surfing lesson from a local guru.


Walk cobblestone streets while discovering the eclectic charm of Valparaiso, recently named a UNESCO World Heritage city for its historic architecture. Visit an enigmatic cemetery with elaborate, above-ground tombs from colonial times, and finish the day with a boat tour of the bay.


Depart from Santiago.

Is It For Me?

This is a great trip for all ages that reveals the many facets of Central Chile. From the Presidential Palace to sleepy fishing villages, fine vineyards to eccentric Valparaiso, this trip has it all.

Knowmad has vast knowledge and operations in Chile; this is a private trip and we are happy to modify excursions, accommodations, and the flow of the itinerary to perfectly suit your travel style and interests.

Have questions? Talk to an expert: 612-315-2894

Important Info

Holiday in Chile Place Setting


Listed prices are approximations. All Knowmad trips are custom and exact pricing is provided in your trip proposal.

  • From $3,500 per person / 2 travelers

type Flexible Date Private Departures. You choose the date, your travel companions, and one of our adventures.

LIGHT TO MODERaTE TRIP Activities include biking, wine tasting, horseback riding, boating & cultural opportunities *optional surfing or wind surfing

LENGTH 7 days – 6 nights

BEGIN / END Santiago, Chile

Air Travel

INTERNATIONAL Airfare is not included in the land cost of our trips. You may arrange your international airfare independently, or we are happy to offer our feedback and assistance in helping you book it.

REGIONAL There is no regional airfare needed for this itinerary.

What's Next?

Ready for the trip of a lifetime? Signing up is easy. Call us at 612-315-2894 or email [email protected] and reserve your spot. Or simply download our registration form, fill it out, and send it back to us along with your trip deposit. Please refer to registration form for terms & conditions.

Weather & When to Go to Central Chile

Central Chile has a Mediterranean climate similar to the middle parts of California, however the seasons are opposite those in North America and Europe. Expect daytime temps between 70-90 °F (21-32 °C) between November and March, and between 45-65 °F (7-18 °C) other times in the year factoring in coastal breezes if in Valparaiso, Vina del Mar or Cassablanca Valley. In other words Central Chile is comfortable year-round however if you’re not going for skiing it is cloudier and cooler between May and October.

Weather in Chile

Prior to your departure, you are provided a detailed pre-trip information packet including a recommended pack list, information about the regions you’ll be visiting, suggested readings, up-to-date health information including any recommended vaccinations and more.


Our trips feature comfortable accommodations that complement their surroundings. We seek out intimacy and character, but never sacrifice cleanliness and security. We also find the best value for quality. In general, our physically moderate to vigorous trips feature hotels classified as 3+ to 4 stars, while less physically demanding trips feature 4+ to 5 star hotels.

As South American travel specialists, we’re experts and have inspected hundreds of properties. Knowmad is happy to suggest upgrades and alternative hotels based on your preferences to ensure your trip is perfect for you. Photos below are from this itinerary’s preferred accommodations. For more specifics, call or write to request more info.

Detailed Itinerary

DAY 1 Santiago

Arrive to Santiago in the morning. You’ll be met at airport and transported to your hotel. After a morning rest and lunch at the oldest restaurant in the city, stroll throughout the city visiting La Moneda Presidential Palace, Santiago’s bustling pedestrian mall, Santa Lucia Hill, and the nearby artesenal market. Dinner is on your own.

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DAY 2 Santiago – Colchagua

Set out on bicycle to discover the culture of Santiago rolling through the bohemian Bella Vista barrio, central market, and the Plaza de Armas. Following the bike ride and lunch at Santiago’s lively fish market, we’ll set out for Chile’s finest wine-growing region, the Colchagua Valley. After checking into a charming countryside inn, we’ll pick freshly grown garden vegetables and learn to make pebre, Chile’s delicious version of salsa, before having dinner in a beautiful and lovingly restored hundred-year-old bread shop.

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DAY 3 Colchagua

After breakfast at the hotel, we’ll head into the town of Santa Cruz and visit the Colchagua museum and the Santa Cruz Plaza, followed by a visit to the reknowned Montes Vineyard for a tour and tasting. After the tasting we’ll return to the hotel for a Chilean asado (barbeque) on the picturesque veranda and have a brief siesta. Following our rest we’ll head to the Viu Manent vineyard, riding horseback through the vineyard seeing first-hand how the grapes are cultivated and grown before a light dinner of wine, cheese and snacks as the sun sets over the valley.

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DAY 4 Coast

This morning we head out on the scenic drive westward to the coast, stopping in a small town for a lunch of empanadas. After an inspiring descent down to the black sands of Matanzas and checking into your private cabana perched over the sea, we’ll meet a local fisherman and cast a line in search of dinner. If you’re lucky, skilled, or both you’ll dine on your catch, otherwise choose from the fresh catch of more experienced fisherman.

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DAY 5 Coast – Valparaiso

Enjoy breakfast overlooking Matanzas beach. Afterwards, if you’re feeling adventurous, take a windsurfing or surfing lesson* from a local guru in Matanzas’ famous wave breaks. For a more relaxed morning choose to watch the waves from the comfort of a seaside wood-burning hot tub after a stroll along the beach. In the afternoon we set out for the bohemian port-city Valparaiso, stopping at the eclectic home of the Nobel prize winning poet Pablo Neruda en route. After lunch we’ll continue on to Valparaiso, cultural capital of Chile. Dinner is on your own with plenty of recommendations in this culinary mecca.

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DAY 6 Valparaiso

After breakfast use the morning to walk the cobblestone streets while discovering the hills of this culture-filled UNESCO world heritage city. After lunch we’ll drive to Valparaiso’s enigmatic cemetery filled with elaborate, above-ground tombs from colonial times before hopping on a small fishing boat to tour the bay.

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DAY 7 Valparaiso – Santiago – Home

After breakfast in the hotel we’ll head back to Santiago and on to the airport.

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Extend Your Adventure

Easter Island

A tropical paradise with history, culture and mystery at every beautiful turn, a visit to Easter Island – the world’s most isolated speck of land – will captivate any traveler. Meander through the picturesque countryside dotted with volcanoes, and learn about the mysterious Moai statues erected by the original Polynesian tribes who inhabited the island. Still today little is known about the statues or their creators. While circumnavigating the island on visits to the diverse Moai sites, you’ll have opportunities to relax on deserted, white-sand beaches, explore volcanic caves with petroglyphs and walk the rim of a seaside volcano. 

Atacama Desert

Looking for unique? Earth’s closest thing to Mars, Atacama will not disappoint. Your trip to this surreal landscape offers countless cultural and adventure excursions to choose from during the day, while spending nights in a true oasis, the Tierra Atacama boutique hotel and spa. Return for a dip in the pool and enjoy a local cabernet with gourmet cuisine. Don’t forget to take advantage of the world’s best moonscape and stargazing. 

Let The Journey Begin

Let the Journey Begin - Knowmad Adventures

Planning a trip to South America might seem a little overwhelming at first. Knowmad offers door-to-door trip planning: first, we listen, and then we help you navigate the seasonal differences and itinerary options, resulting in a holistic, seamless, and custom-crafted experience, all at a guaranteed best value.

The simplest way to get started is to give us a call at 612-315-2894or to fill out this short form so we can learn more about your travel preferences.