THE TOP 20 Chile Holidays (UPDATED 2026)

Santiago: Viña del Mar, Valparaiso, with Casablanca Wine Tasting

Overview Depart Santiago and journey west across the scenic foothills of the Pre-Andes Mountains on a full-day excursion to Chile’s Pacific coast. Your first stop is Viña del Mar, the “Garden City,” where you’ll see its seaside charm, flower-lined avenues, and iconic landmarks. Continue to Valparaíso, a UNESCO World Heritage port city, to explore a vibrant local market, spot coastal wildlife, and enjoy a guided walking tour through its colorful hills, street art, and historic funiculars. Take time for lunch and sightseeing, before returning inland. On the way back, visit the Casablanca Valley, one of Chile’s premier wine regions, for an included wine tasting experience at a local vineyard. Highlights Hotel pickup and drop-off in Santiago Visit Viña del Mar’s gardens, avenues, and oceanfront Explore Valparaíso’s markets, hills, murals, and historic port Free time for lunch and personal exploration Stop in Casablanca Valley for a guided wine tasting

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Santiago: Viña del Mar, Valparaiso, with Casablanca Wine Tasting

10 hoursFree Cancellation

Price varies by group size

Revel in the vibrant color and culture of Valparaiso Port and Viña del Mar on a full-day tour of the coastal cities from Santiago. Travel through Chile’s spectacular countryside, stopping in the picturesque Casablanca Valley to taste Chilean wine, and then arrive in the verdant city of Viña del Mar. Admire the gorgeous beach and revitalize with a delicious seaside lunch (at your own expense), and then take a tour of Valparaiso’s kaleidoscopic sprawl of houses and hills. Capture photographs of street art and hear of the city’s interesting history before returning to Santiago by luxury coach.

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Valparaiso Port and Viña del Mar with Casablanca Wine Tasting

10 hoursFree Cancellation

4.9

(7,600)

from $75

Price varies by group size

Andes Range Tour at Inca Lagoon & InSitu Winery Snack Included

Immerse yourself in the mountainous splendor of the Andes on an exhilarating full-day excursion to In Situ Vineyard from Santiago. With a professional guide, travel through spectacular scenery to one of the most beautiful lagoons in the Andes Mountains; capture photographs of the water’s iridescent turquoise surface and listen to poignant legends of Incan royalty. Ascend to the vertiginous altitude of Hotel Portillo ski resort; and absorb the verdant beauty of the vineyard before pleasuring your palate with wine samples.

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Andes Range Tour at Inca Lagoon & InSitu Winery Snack Included

10 hoursFree Cancellation

4.7

(869)

from $79

Price varies by group size

Maipo Valley Wine Tour with 4 vineyards from Santiago.

10 hoursFree Cancellation

4.9

(2,494)

from $135

Price varies by group size

Traditional Wine Tour in Viña Cousiño Macul Official English

We are a boutique vineyard in the middle of Santiago City that has as a priority to deliver a more human and familiar touch on our tours. Our more than 150 years has taught us that dealing with people with a more delicate and welcoming way is a very fundamental aspect and we put it into practice everyday. We want everyone to feel engage and in love with the history of the Cousiño family as well as with the winemaking process.

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Traditional Wine Tour in Viña Cousiño Macul Official English

1 hourFree Cancellation

4.9

(372)

from $27

"Premium Wine Tour" Viña Cousiño Macul Official english

We are a boutique vineyard in the middle of Santiago City that has as a priority to deliver a more human and familiar touch on our tours. Our more than 150 years has taught us that dealing with people with a more delicate and welcoming way is a very fundamental aspect and we put it into practice everyday. We want everyone to feel engage and in love with the history of the Cousiño family as well as with the winemaking process.

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"Premium Wine Tour" Viña Cousiño Macul Official english

1 hour 30 minutesFree Cancellation

5.0

(135)

from $45

Santiago Markets Small Group Bike Tour

3 hoursFree Cancellation

4.9

(399)

from $43

Special Offer

Santiago: Valparaiso, Viña del Mar & Casablanca Wine Tour

Even if you have limited time in Chile, the charms of Vina del Mar, Valparaiso, and the Casablanca Valley shouldn't be missed. This comprehensive day tour from Santiago includes hotel pickup and covers all three destinations. Explore Vina del Mar's coastal highlights, walk Valparaiso's colorful bohemian neighborhoods, and enjoy a wine tasting at a vineyard in the Casablanca Valley, one of Chile's most celebrated wine regions, a stop that other tours skip.

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Santiago: Valparaiso, Viña del Mar & Casablanca Wine Tour

10 hoursFree Cancellation

Indulge in a sophisticated day of wine tasting on this private tour to Chile's beautiful Casablanca Valley! With your expert LGBT+ guide, you’ll escape Santiago for a day of relaxation and flavor, famed for its elegant cool-climate wines. We will visit two handpicked, premium wineries for expert-led tastings of a diverse portfolio, from the valley's iconic Sauvignon Blanc to impressive red wines. Enjoy the comfort and privacy of your own vehicle. This tour is the perfect blend of luxury and leisure. The Pride Tours Difference: This is more than a tour; it's a relaxed conversation in a safe, welcoming space. We've curated every detail so you can simply relax, enjoy the wine, and be yourself.

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Casablanca Valley: Premium Wine Tour with LGBT+ Guide

6 hoursFree Cancellation

5.0

(6)

from $200

Private Transfer from Santiago Airport to Santiago

15 minutesFree Cancellation

4.2

(333)

from $34

Price varies by group size

New Premium Concha y Toro Tour Includes winetasting & Transport

Enjoy a Chilean wine experience on this wine tasting tour from Santiago to Concha y Toro, one of the largest producers of wine from Latin America, known for wines such as Casillero del Diablo and Don Melchor. With a guide, you'll visit the old summer residence of the Concha y Toro family in Pirque to explore its gardens and enjoy a tasting of three varietals. Select a morning or afternoon departure time when booking.

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New Premium Concha y Toro Tour Includes winetasting & Transport

4 hoursFree Cancellation

3.2

(101)

from $87

Portillo & Inca Lagoon Private Andes Experience + Chilean Wine

9 hoursFree Cancellation

5.0

(5)

from $230

Price varies by group size

Andean Horseback Ride: Scenic Trails & Wine Picnic

4 hoursFree Cancellation

5.0

(187)

from $210

Price varies by group size

Santiago: Full day tour to Valparaiso and Viña del Mar city

Discover the colourful port city of Valparaiso and the garden city of Viña del Mar on this full-day tour of Chile’s Pacific Coast gems, including hotel pick-up and round-trip transport from Santiago. Explore the UNESCO-listed historic quarter of Valparaiso, admire the views from the hilltop elevator (your expense) and opt to visit the house museum of Nobel Prize winner Pablo Neruda. Then, marvel over the landmark flower clock and cool off at the beaches of Viña del Mar.

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Santiago: Full day tour to Valparaiso and Viña del Mar city

10 hoursFree Cancellation

4.1

(199)

from $44

Price varies by group size

Private Santiago City Half Day Tour

4 hoursFree Cancellation

4.1

(423)

from $77

Price varies by group size

Viña Concha y Toro: Premium Wine Center Tour

Discover the new premium tour of the Concha y Toro Wine Centre, in the heart of the Pirque Valley. A sensory and immersive experience The experience begins with a walk through the centuries-old park and the exteriors of the historic Casa Don Melchor. Then live the Casillero del Diablo Sensory Experience and tour the iconic underground winery that brings this iconic brand to life. Visit the exclusive Guarda del Alto Winery, discover the historic landmarks of the vineyard and enjoy a panoramic view from the Mirador Concha y Toro. Tour the Variety Garden and taste four premium wines in a unique setting. End your visit in Plaza Concha y Toro, with dining options and exclusive wine shop. Includes: • Transportation through the facilities • Access to all areas of the route • 4 glasses of premium wine *Experience and tasting only for over 18 years, in the case of minors only transfer service is included.

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Viña Concha y Toro: Premium Wine Center Tour

5 hoursFree Cancellation

4.8

(845)

from $105

You don't have to travel for hours to enjoy the mountainous landscapes of Chile. This private horseback riding tour whisks you to the Andes mountains in just 30 minutes from Santiago, letting you inhale fragrant woodland air as you ride across gentle streams, mountains, and ravines with your guide. At the end of your ride indulge in a picnic lunch of seasonal fruits, cheese, ham, and fresh bread paired with wine.

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Private Horseback Adventure in the Andes, with Picnic & Wine

6 hoursFree Cancellation

4.9

(62)

from $279

Price varies by group size

Cousiño Macul Vineyard and Bahai Temple Cultural Tour with Wine

Discover Chile’s rich winemaking tradition on the tour of the Cousiño Macul Vineyard and the Baha’i Temple. Starting in Providencia, Santiago, you will visit this iconic vineyard with more than a century of history, where you will learn about the winemaking process and enjoy a tasting of three of its best wines. Then, head to the top of Santiago Hill to explore the Bahai Temple, with its unique architecture and spiritual atmosphere. Discover two great traditions on a 4.5-hour tour culminating with breathtaking views of the Chilean capital. - 4.5 hour tour combining wine and culture in Santiago - Visit to the Cousiño Macul Vineyard and tasting of three wines Explore the Baha'i Temple and learn about Baha'i - Enjoy spectacular views of the mountain range and the city of Santiago

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Cousiño Macul Vineyard and Bahai Temple Cultural Tour with Wine

4 hours 30 minutesFree Cancellation

5.0

(2)

from $94

Visit the Cajón del Maipo area on this full-day tour from Santiago. Located southeast of the city, Cajón del Maipo is known for its massifs, hills, and rivers and is a great spot for nature lovers looking to explore some of Chile's great outdoors not too far from Santiago. You'll visit San Jose de Maipo to learn about the area's history, and then travel into the mountains and to a lake. A wine and picnic are provided.

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Cajon del Maipo/Embalse del Yeso, Tradition Folk Picnic included

9 to 10 hoursFree Cancellation

4.5

(2,891)

from $42

Small Group Tour: Cajon del Maipo with Hotsprings plus Picnic and Andinian Zoo

Cajon del Maipo and Hotsprings + Tradition Folk (ticket included)

9 to 10 hoursFree Cancellation

4.1

(477)

from $59

Half-Day Small-Group Panoramic Santiago Tour

Discover the political, cultural, economic heart of Chilean culture with this comprehensive small-group tour around Santiago. Marvel at the city's impressive architecture at sites like the elegant Club Hípico de Santiago (Equestrian Club), see the seat of Chilean power at La Moneda, and check out the city’s trendy side at hip eateries and boutiques of the Bellavista area before finishing at the Central Market, plus much more.

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Half-Day Small-Group Panoramic Santiago Tour

4 hoursFree Cancellation

4.0

(91)

from $40

Price varies by group size

Lastarria Food Tour: Wine, Bites & Social Culinary Experience

Skip the generic tourist snacks for a premium "Best of Chile" immersion. This isn't just a meal; it's a curated journey through the country’s diverse geography and flavors. A Regional Wine Exploration: Discover how Chile’s terroir defines its wine with a flight spanning the sun-drenched central valleys to the cool glacial south. Land & Sea Menu: Savor the pillars of Chilean cuisine, from savory heritage corn recipes and artisanal meats to the briny freshness of Pacific shellfish. Elite Venues: We partner with world-renowned wine destinations and top-tier eateries to ensure professional-grade tastings. History Between Courses: Explore the bohemian soul of Lastarria and the resilient history of the "Burned Church" with a certified guide. True All-Inclusive: From your first Pisco Sour to a full 3-course gourmet lunch, every detail is handled for a seamless, high-end afternoon.

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Lastarria Food Tour: Wine, Bites & Social Culinary Experience

3 hoursFree Cancellation

5.0

(17)

from $109

Trade the bustle of Santiago for a spectacular hike through the Andes Mountains on this small-group tour that takes care of all the logistics. Set out through Chile's Cajón del Maipo en route toward San Jose Volcano, a stratovolcano with a 2.5-mile (4-kilometer) wide caldera. Marvel at the surrounding mountains, glaciers, and rivers as you walk, enjoying a leisurely lunch and time relaxing by a waterfall before returning to the city.

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Andes Day Volcano 8K - Cajón del Maipo

12 hoursFree Cancellation

4.9

(660)

from $150

Tour to Valparaíso, Viña del Mar, Pablo Neruda Museum and Vineyard

Discover the charms of the Casablanca Valley, Valparaiso and Viña del Mar in one day! The experience begins in the Casablanca Valley, famous for its wines, where you will have the opportunity to enjoy a classic tasting in one of its main vineyards surrounded by a wonderful environment full of aromas and landscapes. We will continue the adventure to the picturesque Valparaiso, one of the main ports of the country, where the House Museum of the great poet, Nobel laureate Pablo Neruda is located. This museum known as “La Sebastiana”, where the tour is made with audio guide so you can know each space that preserves collections of maps, curious pieces and relics. Following the experience, you will take a guided walking tour, where you can walk through the most emblematic sectors of the hills of Porteños. We will finish with a panoramic visit to Viña del Mar, where you will know the famous “Flower Clock” and one of the traditional beaches of the city.

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Tour to Valparaíso, Viña del Mar, Pablo Neruda Museum and Vineyard

10 hoursFree Cancellation

4.9

(2,468)

from $111

Top Chile Holidays

100+ results

Top Attractions in Chile

Viña del Mar

Perito Moreno Glacier

Cerro Concepcion

Paseo Gervasoni

Tierra del Fuego National Park

Undurraga Winery (Viña Undurraga)

Viña del Mar

Perito Moreno Glacier

Cerro Concepcion

Paseo Gervasoni

Tierra del Fuego National Park

Undurraga Winery (Viña Undurraga)

Viña del Mar

Perito Moreno Glacier

Cerro Concepcion

Paseo Gervasoni