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Vineyards of Chile

Top Chile Trips & Tours in May 2026

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Discover Chile in May 2026 on one of these 32 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Hiking, Wildlife Viewing, Village Visits, Wine Tasting, and Urban Exploration. Prices for trips in May 2026 range from $156 to $7,815 for a vacation of 5 to 13 days. Choose any of the below 32 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Chile trip planners.
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Chile Wine Adventure
from $3,506
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Chile Wine Adventure

8 Day Itinerary
  • Explore Santiago City
  • Discover Los Dominicos
  • Bike through Colchagua Valley
  • Visit Viña del Mar and Valparaíso
Starts / Ends
Santiago / Santiago
Activity Level
Moderate
Hike, bike, taste wine, and enjoy traditional Chilean cuisine on this week-long tour through the Santiago Valley. Your journey includes a city tour of Santiago's historical sites and a tour of several local wineries. This tour can be customized to increase or decrease the activity level based on your preferences.
Tour Details
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Taste the wonderful wines of the region on a Chile tour
from $156
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Wine Tours - Concha y Toro

½ Day Itinerary
Activity Level
Relaxed
Enjoy a day trip outside of Santiago to one of South America's and one of the world's most renowned wineries - Concha y Toro. The scenery is expansive rolling hills draped with vineyards with the snowcapped Andes mountains as a backdrop. Don't miss the famous Casillero del Diablo - the cellar of the devil!
Tour Details
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Stars in the Atacama Desert sky
from $2,970
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Awasi Atacama Desert

4 Day Itinerary
Activity Level
Relaxed
Spend your nights in San Pedro de Atacama on these 3 to 5-night luxury Chile tours with flexible itineraries that explore the best of the Atacama like the Valley of the Moon, Lasana Valley, and the El Tatio geysers.
Tour Details
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Atacama Desert
from $210
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Atacama Archaeological Tour

½ Day Itinerary
Starts / Ends
Atacama Desert / Atacama Desert
Activity Level
Relaxed
Explore in 2025 with a relaxed journey through the Andes and Atacama Desert. Enjoy easy archaeological visits and stunning landscapes with minimal effort. Perfect for comfort seekers, this trip blends culture and nature in , part of . Plan for 2026 too!
Tour Details
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Stroll past the quaint homes in Valparaiso
from $324
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Vina del Mar & Valparaiso

1 Day Itinerary
Activities
Urban Exploration
Activity Level
Relaxed
Visit two distinct and atmospheric cities with a day tour of Chile's Pacific Coast. Begin in Viña del Mar, a leading beach destination and South America's second popular tourist city. Glimpse the ornate wooden buildings that line this charming coastal town before heading inland to Valparaiso, where you can explore cobblestone streets and wander historical markets.
Tour Details
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The Plaza de Armas is located in the heart of Santiago
from $175
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Explore Santiago

½ Day Itinerary
Activity Level
Relaxed
Start exploring Santiago, the capital of Chile, on this half-day tour! Visit La Moneda, and Plaza de Armas. Climb Cerro Santa Lucía and make your way through Bellavista's neighborhood.
Tour Details
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Chilean vineyards
from $2,075
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Colchagua Valley Wine Escape

3 Day Itinerary
  • Enjoy horse ride at VIK winery
  • Trek across the Colchagua Valley
  • Visit the Lapostolle Winery
Starts / Ends
Santiago / Santiago
Activities
Wine Tasting, Horseback Riding
Activity Level
Relaxed
Sample some of Chile’s internationally renowned wines on this three-day getaway in the enchanting Colchagua Valley, exploring the vineyards in style via walking and horseback riding before spending the nights in luxury accommodations after full days of wine-induced decadence.
Tour Details
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Explore Easter Island
from $1,950
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Classic Easter Island Group tour

5 Day Itinerary
  • See the superb Moai Stone Statues
  • Admire spectacular ancient ruins
  • Discover beautiful volcanoes
Starts / Ends
Easter Island / Hotel Otai
Activities
Archaeological Site Visits
Activity Level
Relaxed
Immerse yourself in the mystical culture, epic landscapes, and ocean views of legendary Easter Island. Visit the mysterious Moai statues, walk and drive around the island’s best natural and archeological sites, and learn more about this fascinating island!
Tour Details
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Whitewater rafting adventure on Chile's Rio Futaleufu
from $900
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Lakes District Adventure

4 Day Itinerary
  • Enjoy rafting on the Petrohue River
  • Discover Perez National Park
  • Bike along Lake Llanquihue
Activity Level
Moderate
Explore the Chile Lakes District regions, with its beautiful natural scenery and opportunities for adventure. Enjoy nature hikes, whitewater rafting, biking, and a taste of the Welsh local culture of Puerto Varas. Combine this short extension with other Chile tours and extensions, or the Chiloe Island Adventure!
Tour Details
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Valparaiso, Chile
from $624
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Valparaiso and Viña del Mar

3 Day Itinerary
  • Visit historic sites of Valparaiso
  • Taste local wines
  • Explore Viña del Mar's beaches
Starts / Ends
Santiago / Casablanca
Activity Level
Relaxed
Enjoy a 3-day tour to the Chilean coast to visit the cities of Valparaiso and Viña del Mar. Explore the chic beach-side cities and taste local wines before returning to Santiago.
Tour Details
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Puerto Varas and Volcan Osorno
from $461
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Osorno Volcano and Petrohue Waterfall

1 Day Itinerary
Starts / Ends
Puerto Varas / Puerto Varas
Activity Level
Relaxed
The Osorno and Petrohue Waterfall Day-Tour is the perfect program for those who love the outdoors. Discover the mysteries hidden in the Cordillera de Los Andes and its majestic Osorno Volcano, one of the highest peaks in southern Chile. Visit Llanquihue Lake, fish for trout at Río Pescado waterfalls, and take pictures of the beautiful Lake of All Saints.
Tour Details
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Explore the vineyards and wineries of Chile on a Chile biking tour
from $534
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Wine Tours - Premium Maipo Valley

1 Day Itinerary
Activity Level
Relaxed
Tour Perez Cruz, a boutique winery located on the estate grounds of the Perez Cruz family, then head towards Santa Rita winery to experience its grape variety garden. Enjoy a delicious lunch in Santa Rita's traditional restaurant, "Doña Paula," a beautiful mansion of colonial architecture with paintings displayed from artistic movements.
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Rainbow over Torres del Paine
from $6,262
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Chile North to South Premium

13 Day Itinerary
  • Discover Santiago
  • Explore the Atacama Desert
  • Hike on epic trails in Perez Rosale
  • Enjoy rafting on Chile's rivers
Activities
Biking, Whitewater Rafting
Activity Level
Easy Active
Discover Chile's awe-inspiring geographical and natural extremes on this upgraded 13-day, multi-destination trip. From the world's driest desert to the volcanic peaks, the wild Patagonian steppe, the country's vineyards, unique activities, and exclusive boutique accommodation, this trip has everything for a deluxe scenic Chilean adventure.
Tour Details
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A magnificent sunset over Atacama's Valley
from $441
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Rainbow Valley & Yerbas Buenas

Itinerary
Starts / Ends
Atacama Desert / Atacama Desert
Activity Level
Relaxed
Start your adventure in San Pedro de Atacama by driving an hour to the ancient archaeological site of Yerbas Buenas. For an hour and a half, walk around the petroglyphs which date back approximately 10,000 years. Embark on another half-day tour of Rainbow Valley, home to colorful mineral-rich rock formations.
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Looking out over the Atacama Desert
from $333
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Sandboarding at Mars Valley

Itinerary
Starts / Ends
Atacama Desert / Atacama Desert
Activity Level
Moderate
Experience the joy and thrill of sandboarding at Mars Valley in the beautiful Bolivian Altiplano! On a day off from the salt mines, be taken to the best sand dunes in town. Descend an incredible 400 feet (120 meters) on a sandboard. Take home unforgettable memories of this surreal landscape and its deep red color contrasted by its rich dark hue.
Tour Details
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Hot spring in the Atacama
from $316
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Puritama Hotsprings

Itinerary
Starts / Ends
Atacama Desert / Atacama Desert
Activity Level
Relaxed
Take the half- day Puritama Hotsprings tour and enjoy the serenity and rejuvenating properties these mineral springs have to offer. The natural waters have a constant temperature of 35°C/95°F, making them comfortable and relieving muscle tension. This is an ideal way to relax after a long day visiting Machu Picchu and the surrounding areas.
Tour Details
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Puntiagudo Volcano, a snow-cappedd volcanic chain in Chile, near Osorno Volcano
from $2,650
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Chile's Three Lakes & Volcanoes Crossing

Chile Small Group Tour - 4 Day Itinerary
  • Hike the Desolacion Trail
  • Boat ride to Puntiagudo Valley
  • Hike to Lake Rupanco
  • Visit hot springs by Lake Rupanco
Starts / Ends
Puerto Varas / Puerto Varas
Activities
Hiking, Village Visits, Homestays
Activity Level
Moderate
Join a 4-day trek in Chile's Lake District, connecting three lakes and volcanoes. Hike the Desolación Trail to Lake Todos Los Santos, take a boat to Puntiagudo Valley, and trek 8.5 km to a family lodge. On day three, hike 18 km to Lake Rupanco for stunning views. End with a soak in natural hot springs before returning to Puerto Varas.
Tour Details
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The Island of Chiloé
from $7,075
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The Islands of Chiloe & The Route of the Parks of Patagonia

10 Day Itinerary
  • Scenic walking tour of Puerto Varas
  • Osorno Volcano & Rewilding Activity
  • Natural Wonders of Chiloé
  • Visit Castro & Culinary Adventures
  • Explore the Route of the Parks
  • Chaitén Volcano & Scenic Return
Starts / Ends
Puerto Varas / Puerto Varas
Activities
Wildlife Viewing, Cooking Classes, Local Market Visits, Volunteering
Activity Level
Easy Active
Join this 10-day adventure through Chiloé and Patagonia's Route of Parks, beginning in Puerto Varas. Discover Chiloé's culture and landscapes while exploring hidden trails and participating in rewilding projects. Experience the breathtaking scenery of Patagonia, with its temperate rainforests, volcanoes, fjords, and the Andes.
Tour Details
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