THE TOP 20 Chile Holidays (UPDATED 2026)

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

...More

4.8

(230)

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

10 hoursFree Cancellation

from $65

Price varies by group size

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.

...More

4.9

(113)

"Premium Wine Tour" Viña Cousiño Macul Official english

1 hour 45 minutesFree Cancellation

from $45

Special Offer

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.

...More

4.8

(6,928)

Valparaiso Port and Viña del Mar with Casablanca Wine Tasting

10 hoursFree Cancellation

from

$75

$79

Price varies by group size

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.

...More

4.9

(357)

Traditional Wine Tour in Viña Cousiño Macul Official English

1 hour 15 minutesFree Cancellation

from $27

4.9

(2,319)

Maipo Valley Wine Tour with 4 vineyards from Santiago.

10 hoursFree Cancellation

from $135

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.

...More

4.7

(791)

Andes Range Tour at Inca Lagoon & InSitu Winery Snack Included

10 hoursFree Cancellation

from $79

Price varies by group size

4.4

(18)

Santiago: Bali Hai Dinner & Show, Transport and Wine refill

4 hoursFree Cancellation

from $106

Price varies by group size

4.6

(1,949)

Discover Santiago: Tourist Bus, Cerro San Cristobal and Wine

2 hoursFree Cancellation

from $115

Explore the renowned Colchagua Valley, one of the world's premier wine destinations, known for its picturesque vineyard-covered hills, century-old vines, charming colonial estates, and cutting-edge wineries. Just a day trip from Santiago, this region has transformed over the past two decades from a tranquil farming area into one of Chile's largest and most vibrant wine-producing regions. The unique geography of the Colchagua Valley, situated in the southern Rapel Valley, benefits from the cooling Pacific breezes and Andean winds. These natural influences create ideal conditions for growing high-quality grapes, preserving acidity, and producing vibrant red wines with great freshness and aging potential. The valley is particularly known for its Carmenere, Cabernet Sauvignon, and Merlot varieties, while newer coastal plantations show promise for cool-climate white wines.

...More

5.0

(10)

Full Day Colchagua VIK - Montes Wine Experience

10 to 12 hoursFree Cancellation

from $399

Price varies by group size

Save time and hassle by pre-booking this private transfer from your Santiago hotel to Santiago International Airport. An air-conditioned minivan picks you up from your accommodation—or another meeting point—in the districts of Providencia, Las Condes, Vitacura, and Santiago Centro, then transports you to the airport. Don't worry if you have an early or late flight as his service is available 24 hours a day.

...More

4.5

(91)

Private Transfer from Santiago Hotel to SCL Airport

30 minutesFree Cancellation

from $34

Price varies by group size

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.

...More

5.0

(15)

Lastarria Food Tour: Wine Tasting, Bites & Culinary Experience

3 hoursFree Cancellation

from $159

Likely to Sell Out

3.8

(330)

New Concha y Toro Tour Marques with class, extra tasting y food

4 hoursFree Cancellation

from $115

3.7

(224)

Visita Guiada Premium Centro del Vino Concha y Toro

2 hoursFree Cancellation

from $55

5.0

(4)

Private Transportation from Santiago Tour Viña Concha y Toro and Museum

5 hours 30 minutesFree Cancellation

from $110

Price varies by group size

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.

...More

4.9

(62)

Private Horseback Adventure in the Andes, with Picnic & Wine

6 hoursFree Cancellation

from $279

Price varies by group size

Likely to Sell Out

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.

...More

3.2

(99)

New Premium Concha y Toro Tour Includes winetasting & Transport

4 hoursFree Cancellation

from $87

The journey takes you to the heart of the Andes to explore the enchanting Laguna del Inca, a turquoise lake surrounded by soaring peaks and the iconic Portillo ski resort. This serene alpine setting offers breathtaking views and a deep connection with nature. Designed for small groups, the tour ensures a personalized experience that combines world-class wines, stunning landscapes, and the majestic beauty of the Chilean mountain range

...More

4.8

(47)

Andes Portillo & Aconcagua wine tour semi private

10 hoursFree Cancellation

from $129

Head out to the charming coastal city of Valparaiso, known for its beautiful old lanes and huge collections of colorful murals with this trip from Santiago. Your guide will pick you up from your hotel and take you through the countryside to Valparaiso, where you'll visit a local seafood market and have the option to visit one of the former home of poet Pablo Neruda. You'll also stop by the Punta Los Angeles lighthouse before making your way out to a Casablanca Valley vineyard for a tasting on your way back to Santiago.

...More

4.8

(18)

Valparaiso Private Tour with Wine Tasting from Santiago

9 to 10 hoursFree Cancellation

from $195

Price varies by group size

4.4

(1,660)

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

9 to 12 hoursFree Cancellation

from $41

Spend a day in the colorful, hilly city of Valparaiso with a guide by your side. This private tour from Santiago takes you to the UNESCO World Heritage city, to see traditional architecture and ride on the city's famous funiculars. Then get the chance to spend some time in the town of Concón or enjoy a wine tasting in the Casablanca Valley (own expense) before returning to your Santiago hotel.

...More

5.0

(22)

Private Valparaíso Day Tour with Wine or Coast Option

8 to 9 hoursFree Cancellation

from $275

Price varies by group size

This private tour of Cajon del Maipo and Embalse el Yeso lets you walk to waterfalls, sip Chilean wines, and take in stunning Andes Mountain scenery in just one day. Admire views as your guide handles the drive across the Maipo Valley, stopping as often as you want to take photos or ask questions—a private tour means you can customize your itinerary. Details like a picnic breakfast and wine tasting bring effortless luxury to the day.

...More

4.8

(17)

Private Andes Day Trip Maipo Valley with Concha Y Toro Wine Tour

10 hours

from $270

4.9

(15)

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

5 to 6 hoursFree Cancellation

from $250

Price varies by group size

Being a part of this tour will take you on a full day tour to experience the Colchagua Wine Valley: one of the most beautiful wine valleys in Chile for its geography, mountains and identity. The valley is known for being one of the places with the most wine and agricultural production in Chile offering the most emblematic grapes such as: Cabernet Sauvignon, Malbec, Merlot, Syrah and Carmenere.

...More

4.0

(3)

Colchagua Full Day Wine Tour: Casa Silva & L'Apostolle Wineries

9 to 10 hours

from $258

Likely to Sell Out

Vik Winery, ranked as the 2nd best in the world, is a captivating gem nestled in Santa Cruz. Its harmonious fusion of tradition and innovation shines through meticulous vineyard care and exquisite architecture. Expertly guided tastings unveil wines that reflect the essence of the land and the dedication of skilled hands. Vik Winery's journey is a testament to passion, precision, and an unwavering pursuit of perfection, making each visit a narrative of creativity and a deep bond with the land.

...More

4.6

(8)

Private VIK Winery (2nd World Best Wine) & Transfer to Hotel

6 to 7 hours

from $320

Price varies by group size

Top Chile Holidays

100+ results

Top Attractions in Chile

Perito Moreno Glacier

Viña del Mar

Cerro Concepcion

Corporate Museum of Archaeology and History Francisco Fonck

Tierra del Fuego National Park

Undurraga Winery (Viña Undurraga)

Perito Moreno Glacier

Viña del Mar

Cerro Concepcion

Corporate Museum of Archaeology and History Francisco Fonck

Tierra del Fuego National Park

Undurraga Winery (Viña Undurraga)

Perito Moreno Glacier

Viña del Mar

Cerro Concepcion

Corporate Museum of Archaeology and History Francisco Fonck