Santiago Tours in May 2027
Planning for a trip to Santiago during May? We offer 20+ tour packages to Santiago departing in May 2027 that have 10+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Santiago on your May holiday.
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10 Best May 2027 Tours in Santiago
Join one of these handpicked Santiago May 2027 tour packages, tailored to the season.
Imagine a weekend where rolling vineyards, award-winning wines, and gourmet cuisine fill your days. The 3 Day Wine & Dine Tour in Chile’s Colchagua Valley invites you to indulge in the region’s celebrated cabernet sauvignons, malbecs, merlots, and carménères, all set against a tranquil rural backdrop just 180 km south of Santiago. Enjoy guided wine tastings, stroll through lush vineyards, savor exquisite meals, and even opt for a horseback ride if you’re feeling adventurous.
Perfect for couples or anyone seeking a romantic escape, this tour lets you tailor your stay—choose between a boutique hotel in Santa Cruz or a cozy countryside lodge. The Colchagua Valley’s rich culture and award-winning wines make this getaway special. Its unique blend of refined dining, scenic landscapes, and immersive wine experiences ensures that every moment feels like a celebration of Chilean hospitality and flavor.
3 days
fromUSD 965
Concha y Toro New Experience available from May 15, 2025
The Concha y Toro Wine Center is a space where Chilean winemaking tradition merges with innovation and modernity.
This new destination offers visitors a unique and immersive experience that takes them through centuries of history, art, gastronomy, and, of course, the finest wines of the house.
The tour begins with hotel pickup to head to the Concha y Toro vineyard. Once we arrive, our tour begins with a visit to the century-old, 22-hectare park and the exterior of the iconic Don Melchor House, which dates back to 1883. At this point, visitors can admire the estate’s original architecture, which faithfully preserves the essence of its time, immersing them in the rich winemaking history of Chile.
Next, the journey continues with the new Casillero del Diablo Sensory Experience, where visitors will discover what makes Chile an ideal place for winemaking, while learning about wine itself and its production process. The tour includes new rooms dedicated to the iconic Casillero del Diablo brand, highlighting its legacy and importance within the company, followed by access to the historic underground Casillero del Diablo cellar.
The experience then leads to the Alto Aging Cellar, a space dedicated to the aging of Concha y Toro’s high-end wines. Here, visitors can explore an exclusive gallery that reflects on the four great milestones in the winery’s history, showcasing its legacy and impact on global viticulture.
From the Concha y Toro Viewpoint, guests can enjoy stunning panoramic views of the Pirque vineyard and explore the Varietal Garden, which features the main vitis vinifera varieties used in global wine production. This part of the experience also includes the tasting of four distinguished wines from the winery.
The tour continues in the Concha y Toro Plaza, a space dedicated to wine, gastronomy, and art. Here, visitors can explore the iconic Concha y Toro Cellar and enhance their visit with a wine and culinary experience at Restaurant Bodega 1883 or La Gran Barra Bodega 1883, where they can enjoy a wide selection of Concha y Toro wines.
To conclude this experience, guests can visit the new Wine Center Store, offering a broad variety of exclusive Concha y Toro wines and wine-inspired products—perfect souvenirs to remember this memorable visit.
Return to Santiago to drop you off at your hotel
5 hours
fromUSD 128
Ready to experience Chile’s vibrant coast in just one day? The "Full Day Tour Valparaiso, Viña del Mar and Casablanca" is a small-group adventure perfect for families seeking culture, color, and a taste of renowned Chilean wine.
Departing from Santiago, this nine-hour trip whisks you to the UNESCO-listed streets of Valparaíso, where you’ll ride historic funiculars through hilltop neighborhoods bursting with murals and charm. Next, soak up the seaside ambiance of Viña del Mar—stroll the beach, marvel at a genuine Easter Island Moai, and snap a photo at the famous flower clock.
Relish a traditional lunch with regional flavors before toasting the day’s discoveries in the esteemed Casablanca Valley wine region. With seamless hotel pick-up and drop-off, this tour’s unique selling point is its rich blend of iconic sights, hands-on experiences, and local flavor—all packed into a single, unforgettable day.
9 hours
fromUSD 130
Wine, gourmet cuisine, and the breathtaking landscapes of the Southern Andes await on this 14-day luxury food and wine tour through Argentina and Chile. Designed with both experienced travelers and seniors in mind, this guided journey blends sophisticated tastes with the natural wonders of Patagonia and the Lake Districts.
Start in Buenos Aires, the Paris of South America, where you’ll savor exquisite Argentine dinners paired with local wines and stroll through the city’s iconic milongas. From there, travel to Bariloche, renowned for its lakes and chocolate, and cross the majestic Andes into Chile, soaking in panoramic vistas of lakes, volcanoes, and snow-capped peaks.
Experience the authentic gaucho lifestyle in San Antonio de Areco, visiting traditional ateliers and historic pulperias in the heart of the pampas. Throughout the tour, you’ll indulge in curated wine tastings, gourmet meals, and cultural immersions designed to elevate your senses.
What makes this tour package truly unique is the seamless blend of luxury, local tradition, and natural beauty—offering guests a refined yet adventurous exploration of South America’s most celebrated regions.
14 days
fromUSD 12,600
Marvel at the universe without ever leaving the ground on the Observatory Stargazing Tour from Santiago—a celestial journey designed for the curious and the contemplative. Located just 40 minutes from the city, this private observatory in the Andes offers an intimate introduction to the night sky, guided by an expert astronomer.
Begin with a fascinating presentation on the cosmos, then step outside to observe the heavens through the naked eye, binoculars, and finally state-of-the-art telescopes. The tour wraps up with wine, cheese, and engaging conversation, providing the perfect setting to reflect on the wonders you’ve witnessed.
The unique selling point is the boutique, personalized setting—offering a rare chance to explore the Chilean sky’s clarity and depth, all capped with gourmet refreshments. For those who yearn to see beyond the city and the everyday, this trip is an inspiring and unforgettable stargazing experience.
4 hours
fromUSD 265
Let the hills of Valparaíso enchant you on this immersive private tour of Chile’s most colorful port city. Ride a historic funicular up the steep slopes, sip coffee in cozy hillside cafes, and wander through bohemian alleyways adorned with street art and artisan boutiques. Soak up panoramic views over the UNESCO-listed harbor before choosing between a bay boat trip—meeting sea lions up close—or a visit to Pablo Neruda’s eclectic house, La Sebastiana. The tour’s USP? Its deep dive into the unique character and cultural quirks of Valparaíso, guided by locals who reveal both well-known highlights and hidden corners. Perfect for travelers eager to capture the city’s creative spirit and dramatic scenery in a single day trip.
10 hours
fromUSD 200
Embark on the Best of Argentina and Chile tour, a 25-day adventure starting and ending in the vibrant city of Buenos Aires. This extensive journey takes you through 12 captivating destinations across Latin America, offering an immersive experience in the diverse landscapes and rich cultures of Argentina and Chile.
Begin your exploration in Buenos Aires, delving into its lively culture and renowned gastronomy. Traverse the country to the breathtaking Iguazu Falls, where you'll marvel at the sheer power and beauty of nature. Head north to discover the colorful landscapes that define this region before venturing to the southern tip of Patagonia. Here, you'll be enchanted by pristine lakes, towering glaciers, and the majestic beauty of the wilderness.
Cross into Chile to explore Santiago, the bustling capital, with its unique cultural charm and culinary delights. Experience the stark, otherworldly beauty of the Atacama Desert, home to flamingos and surreal landscapes. Conclude your journey with a visit to Torres del Paine National Park, one of the natural wonders of the world, known for its stunning peaks, glaciers, and diverse wildlife.
This tour package includes comfortable hotel accommodations, expert guides, and delicious meals, ensuring a seamless and unforgettable travel experience. Discover the best of Argentina and Chile, where every stop offers a new and awe-inspiring adventure.
25 days
fromUSD 6,555
13% Off Today
Curious about what makes South America so irresistible? The "Premium Chile, Argentina & Brazil" tour package invites you to explore the vibrant cities and breathtaking natural wonders of these three dynamic countries over 15 indulgent days. Begin your journey in Santiago, an artistic hub alive with energy, before wandering the colorful hills of Valparaiso. Venture into Mendoza, the cradle of Argentina’s famed Malbec wines, and be swept away by Buenos Aires’ intoxicating blend of European elegance and Latin passion. The adventure continues at the awe-inspiring Iguazu Falls, straddling the border with Brazil, before concluding in Rio de Janeiro—renowned for its stunning landscapes and lively spirit. Designed with a relaxed, easy pace, this trip is ideal for seasoned globetrotters and travelers seeking both comfort and cultural depth. Guided by passionate local experts, you’ll experience authentic flavors, stories, and sights at every turn. The unique selling point? Intimate group sizes and immersive experiences reveal the true heart of each destination, ensuring you savor every moment in style and ease.
15 days
USD 10,545fromUSD 9,205
3% Off Today
See the sights of Santiago, enjoy wine tasting in Casablanca Valley and get up close with Eva Peron’s famous balcony in Buenos Aires—all on this immersive tour of South America. Step out with a Local Expert in Brazil for a stunning walk past the misty rainbows and thundering gravity of Iguassu Falls—with panoramic views of San Martin Island. In Rio de Janeiro, Enjoy an authentic lunch at a local churrascaria, a traditional Brazilian steakhouse and quintessential Brazilian experience. Across the border in Argentina, Buenos Aires beckons with a once in a lifetime choice to join South America’s Gaucho cowboys for a horseback ride through the rugged wilderness or a guided sojourn around the Estancia, to learn about cattle-raising and life on the ranch.
12 days
USD 10,598fromUSD 10,280
3% Off Today
Set out on the grandest of South American tours as you discover Lima, the City of the Kings, explore the salt pans of the Sacred Valley and see the mysterious Machu Picchu up close, with an expert-led tour of the lost city. Cruise Lake Titicaca to the Uros Floating Islands, where locals collect reeds to create their floating homes and pause in the Casablanca Valley for a wine tasting at the boutique Kingston Family Winery. In Buenos Aires, take in the balcony made famous by the former First Lady of Argentina, Eva Peron, and adventure onwards to the thundering cascades of Iguassu Falls. Across the Brazilian border in Rio de Janeiro, dial down the pace with cocktails on Copacabana Beach and an authentic lunch at a local churrascaria, a traditional Brazilian steakhouse and quintessential Brazilian experience.
23 days
USD 16,821fromUSD 16,316
See all Santiago May 2027 Tours
Top Santiago Tour Activities for May 2027
From wine tasting tours to city sightseeing and others, here are some popular tour activities in Santiago with departures in May 2027.
Santiago May 2027 Tours for all Age Groups
Santiago tours in May 2027 designed for all ages—families, young adventurers, seniors, and everyone in between.
Santiago May 2027 Tour Types
Discover Santiago May 2027 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Santiago Travel Styles
Explore Santiago with our diverse travel styles! Choose from luxurious tours that pamper you with comfort and elegance, or budget-friendly options that let you experience the beauty of Santiago without breaking the bank. Whether you're indulging in fine dining or discovering hidden gems, there's a perfect adventure waiting for you.
Get a customized trip to Santiago in May 2027
Plan a multi-country or regional adventure across Santiago in May 2027, with help from a local expert.
Omar VillegasTravel Expert in Chile
Maria SzlafszteinTravel Expert in Argentina, Bolivia, Brazil, Chile, Ecuador, Paraguay, Peru & Uruguay
Clara GonzalezTravel Expert in Argentina, Bolivia, Brazil, Chile, Ecuador, Paraguay, Peru & Uruguay
Ezequiel Fernandez EstelrichTravel Expert in Argentina & Chile
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