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

Member Pricing

Maipo Valley Wine Tour: 4 Wineries, Great Views, Fun Tastings

10 hoursFree Cancellation

Price varies by group size

Member Pricing

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

Price varies by group size

Member Pricing

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

Price varies by group size

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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

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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

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Viña Santa Rita sits in the heart of the Maipo Valley, at the foot of the Andes, just 45 minutes from Santiago. It is one of Chile's most iconic wineries, founded over 130 years ago. The estate is a declared National Historic Monument. Few wineries in South America carry this much history. This is more than a wine tour. You walk through a century-old park. You explore cellars where 120 patriots once took refuge during Chile's fight for independence. You taste internationally awarded wines in small, unhurried groups. Three tour options let you choose the experience that fits you. Whether it is your first vineyard visit or your hundredth, the day stays with you. Escape to the countryside without ever leaving Santiago.

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Santa Rita Premium Tour 5 Wine Tasting & Transportation

4 hours 30 minutesFree Cancellation

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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

Price varies by group size

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Taste 10 Types of Wine in 3 exclusive Casablanca’s Vineyard

5 to 6 hoursFree Cancellation

Price varies by group size

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Punta Arenas : Typical Chilean Cooking Class + Chilean Wine

What makes this class special? Learn to cook the most traditional classics of Chilean cuisine while toasting with quality and renowned Chilean wines. Enjoy the best of our wines and gastronomy while learning interesting facts about our country and its flagship dishes. An Authentic & Homemade Class : Traditional recipes handed down with passion. 100% Practical : Put your hands on the dough from the first minute. Intimate environment: Small groups for a personalized experience. Location: depends on the size of the group. Location confirmation 1 to 2 days before class. Immersive local experience for small groups. For All : No previous experience needed. Just want to have fun and learn! At the end, you will sit down to enjoy the banquet that you prepared yourself, a delicious memory that you will take from Chile. Book your place and turn your trip into a palate experience!

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Punta Arenas : Typical Chilean Cooking Class + Chilean Wine

2 hours 30 minutesFree Cancellation

Price varies by group size

Member Pricing

Private Tour: Viña del Mar and Valparaíso Tour with Wine Tasting in Casablanca Valley

8 hoursFree Cancellation

Price varies by group size

Special Offer

Lastarria Food Tour: Wine, Bites & Social Culinary Experience

Our Lastarria food and wine tour brings Chilean regional flavors together through a guided neighborhood walk, wine pairing, gourmet bites, and a three-course lunch. Begin at one of the best wine bars in the world, with signature Chilean labels and pairings such as corn croquettes and artisanal beef. A “North to South” flight traces how the Atacama Desert, central valleys, and glacial south shape different wines. The meal starts with a Pisco Sour and offers a choice of Pacific shellfish, premium meats, or seasonal garden dishes. Our local guides shares stories about Chilean culture and Lastarria’s history, including Iglesia de la Vera Cruz, also featured as the “Burned Church.” The shared format keeps the focus on conversation and local culture. Recommendations for food, shopping, and things to do afterward round out the visit.

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Lastarria Food Tour: Wine, Bites & Social Culinary Experience

3 hoursFree Cancellation

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Start your journey from Santiago with a visit to a vineyard in Casablanca Valley, one of Chile’s top wine regions. Enjoy a guided wine tasting and savor the flavors of this cool-climate area—a perfect start to your day. Next, explore Viña del Mar, the “Garden City.” Admire the iconic Flower Clock, stroll along beaches, and visit landmarks like the Moai statue at the Fonck Museum, an authentic piece of Easter Island history. Continue to Valparaíso, a UNESCO World Heritage city known for colorful streets, vibrant murals, and steep hillsides. Wander through bohemian neighborhoods, discover hidden stories, and experience the creativity of this unique port city. Finally, the tour concludes at the Valparaíso Cruise Port, convenient for travelers continuing their journey. Experience the wines of Casablanca, the charm of Viña del Mar, and the culture of Valparaíso in one seamless day trip!

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Santiago to Valparaiso Cruise Port: Wine & Valparaiso Tour

8 hoursFree Cancellation

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Viña Del Mar-Valparaiso -Casablanca -Reñaca-Oceanic Rock-Concon

9 to 12 hoursFree Cancellation

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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

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Experience Santiago with this small-group, guided, multi-stop, full-day tour that includes transportation in an air-conditioned vehicle between stops. Learn about the city’s origin story, the military coup of 1973, and modern-day life. Visit places like the Metropolitan Cathedral of Santiago, La Moneda, and Plaza de Armas. Wander in modern and bohemian neighbourhoods and stop at an equestrian club.

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Private Santiago City Tour with Cable Car

5 hoursFree Cancellation

Price varies by group size

Member Pricing

"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

Special Offer

Explore beyond Santiago—and see several of Chile's top coastal destinations, all in a single trip—with this seamless, full-day tour. Following morning pickup from your hotel, set off with just a small group for company. Head first to picture-perfect Viña del Mar; then, continue to Valparaiso, where you'll explore its colorful murals and street art. Finally, enjoy an included wine tasting in the Casablanca Valley before returning to the city.

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Valparaíso Viña & Casablanca Wine Tasting from Santiago (Max 7)

10 hoursFree Cancellation

Price varies by group size

Member Pricing

Premium Wine Tasting in Santiago de Chile

40 minutesFree Cancellation

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Venture to the famed winemaking region of Maipo Valley and visit Undurraga Winery, one of the most prestigious wineries in Chile. Explore the vineyards and underground cellars with a professional guide who shares viticulture knowledge on the Sibaris tour, named after the Sibaris Carménerè Gran Reserva 2013, a gold medal winner. Taste several emblematic wines under the Undurraga label and receive a souvenir wine glass! Round-trip hotel transport is provided from Santiago on this half-day tour.

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Undurraga Wine Tasting Tour from Santiago

4 to 5 hoursFree Cancellation

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Enjoy a 100% private tour with hotel pick-up, flexible timing, and a relaxed pace, with no other guests. In the Casablanca Valley, sample up to four distinctive wines, including a rare blue wine and a chocolate-inspired wine. Meet friendly alpacas and browse jewelry crafted from genuine Chilean lapis lazuli. Continue to Viña del Mar to see the iconic Floral Clock and an authentic Moai from Easter Island. In Valparaíso, enjoy a 30-minute boat ride across the bay before discovering this UNESCO World Heritage Site on a guided walking tour through colorful hills, vibrant street art, historic funiculars, and breathtaking viewpoints. Enjoy lunch overlooking the bay. On the way back, return to Casablanca for a guided visit to a premier sparkling wine winery, ending with a tasting of three exceptional sparkling wines. An elegant journey through Chile's finest wines, coastal landscapes, and cultural treasures.

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Santiago: Private Valparaíso + Boat Ride + Sparkling Wine

10 hours 30 minutesFree Cancellation

Price varies by group size

Member Pricing

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

Member Pricing

Private Santiago City Half Day Tour

4 hoursFree Cancellation

Price varies by group size

Member Pricing

Santiago Markets Small Group Bike Tour

3 hoursFree Cancellation

Top Chile Holidays

100+ results

Must-Dos in Chile

Perito Moreno Glacier

Viña del Mar

Cerro Concepcion

Santa Rita Winery (Viña Santa Rita)

Tierra del Fuego National Park

Undurraga Winery (Viña Undurraga)

Perito Moreno Glacier

Viña del Mar

Cerro Concepcion

Santa Rita Winery (Viña Santa Rita)

Tierra del Fuego National Park

Undurraga Winery (Viña Undurraga)

Perito Moreno Glacier

Viña del Mar

Cerro Concepcion

Santa Rita Winery (Viña Santa Rita)