48 Hours in Santiago Itinerary for Solo Travellers DAY ONE: Historic Streets & Andean Sunsets
Morning
Solo travellers, begin your 48 hours in Santiago layover with a sunrise stroll through the Plaza de Armas, the beating heart of Chile’s capital and follow our Santiago itinerary. There’s something magical about experiencing this historic square before the crowds arrive. The morning light catches the colonial architecture just right and you can almost hear the echoes of centuries past. Join the free walking tour that meets daily at 10 AM right by the cathedral. These local guides are absolute gems who’ll share stories that no guidebook ever captures.
⚠️ Tip: The walking tours run daily at 10 AM and 3 PM, but I always recommend the morning slot. You’ll beat the heat and have more energy to explore afterward.
Late Morning
After soaking up Santiago’s history, wander through the pedestrian streets surrounding the plaza. The Paseo Bandera and Paseo Huérfanos are lined with street performers, local vendors and some of the most vibrant murals I’ve seen anywhere in South America. As a flight attendant, I’ve learned that the best way to understand a city is to get deliciously lost in its streets and Santiago rewards wanderers.
Lunch
Escape to Mestizo for a lunch that perfectly captures Santiago’s sophisticated side. I’ve spent countless layovers on their stunning terrace overlooking Parque Bicentenario while I savour modern Chilean cuisine. The open-air architecture blends wood, stone and glass seamlessly. When the afternoon breeze picks up, the staff thoughtfully offer soft blankets — a gesture that never fails to make me smile.
Why Mestizo is Special: This isn’t just lunch; it’s a celebration of Chilean terroir. The menu showcases local ingredients with Latin American flair, while the wine list reads like a love letter to Chilean viticulture. I once had a memorable conversation with the sommelier about a particular Carmenère that paired beautifully with their signature lamb dish. It’s the kind of place where time slows down, and you remember why you love to travel.
Afternoon
The crown jewel of Santiago awaits: San Cristóbal Hill (Cerro San Cristóbal). At 860 meters above the city, this is where Santiago reveals its true majesty. I always recommend the funicular for the nostalgic charm — it’s been carrying visitors up the hill since 1925. But if you’re feeling adventurous, the teleférico (cable car) offers unparalleled views during the ascent, with the Andes Mountains creating a dramatic backdrop.
At the summit, the 14-meter statue of the Virgen de la Inmaculada Concepción stands guard over the city. The benches at her feet are where Pope John Paul II held Mass in 1984 and on clear days, you can see all the way to the Pacific Ocean.
📷 Photo Tip: Golden hour here is absolutely magical. The cable car ride during sunset creates some of the most Instagram worthy shots you’ll ever capture, with the city lights beginning to twinkle below.
Evening
As the sun begins its descent behind the Andes, make your way to Luna Bar atop the AC Hotel by Marriott. I’ll never forget my first time stepping onto that terrace, the Andes Mountains framed by Santiago’s skyline, bathed in that perfect golden hour light that photographers dream about. The mixologists craft cocktails that are as creative as they are delicious and the Spanish-style tapas add just the right touch of sophistication.
✨ Unique Touch: If you only have one night to let loose in Santiago, Sarita Colonia should be at the top of your list. This isn’t just dinner; it’s theatre. The moment you walk in, you know you’re in for something extraordinary. The Peruvian-Asian fusion menu is as bold as the décor and the energy is absolutely electric. It’s the kind of place that becomes a story you’ll tell for years.
48 Hours in Santiago Itinerary DAY TWO: Wine Country & Culinary Artistry
Morning
Day two is all about what Chile does best: wine. The Casa Valley Wine Region is just a short journey from Santiago, but it feels like stepping into another world entirely. Rolling vineyards stretch toward the Andes, and each winery tells its own story of terroir and tradition. I’ve discovered some incredible boutique producers here that you’d never find in international markets. True hidden gems of the wine world.
⚠️ Insider tip: Book your wine tour the day before and ask your hotel concierge for recommendations. Many tours include transportation, which is ideal if you plan to do proper tastings.
Late Morning
Each winery in the Casa Valley has its own personality from centuries-old family estates with underground cellars to sleek, modern operations with gravity-fed systems. I particularly love the smaller boutique wineries where the winemaker might personally guide your tasting. There’s something magical about sipping a Carmenère while the person who crafted it explains the nuances of the terroir.
Lunch
Return to Santiago for what might be the highlight of your culinary journey: Bocanáriz. This isn’t just one of my favourite restaurants in Santiago; it’s become a pilgrimage site for wine lovers worldwide. Housed in a beautifully restored historic building, it seamlessly combines a wine bar, restaurant, and shop. Their Wine Spectator award-winning list has been recognised for six consecutive years and for good reason.
Why Bocanáriz is Special: As a solo traveller, I’ve never felt more welcomed anywhere. The sommeliers here are artists who paint with wine, offering impromptu tastings and sharing stories behind each bottle. I once spent an entire afternoon here, moving from a crisp Sauvignon Blanc to a complex Cabernet, each paired with small plates designed to elevate the wine. The duck with red wine reduction remains one of my most memorable meals anywhere in the world.
Afternoon
Wander through the vibrant Bellavista neighbourhood, Santiago’s bohemian heart. The colourful street art tells stories of Chile’s complex history and the eclectic mix of galleries, boutiques, and cafés creates an atmosphere that’s both creative and relaxed. Don’t miss La Chascona, Pablo Neruda’s whimsical house-turned-museum, where the poet’s love affair with his muse Matilde comes alive through quirky architecture and romantic details.
Evening
End your Santiago adventure with dinner at Don Carlos Piano Bar, where old-world elegance meets exceptional cuisine. This is Santiago’s answer to a classic steakhouse — think perfectly aged beef, an extensive wine list and live piano music that creates the most wonderfully nostalgic atmosphere. It’s the kind of place where conversations linger over the last glass of wine and you realise that 48 hours in Santiago has somehow felt like a lifetime of experiences.
✈️ Flight Crew Tips
•👟 Wear comfortable shoes. Santiago is a very walkable city, and you’ll want to explore on foot.
•🍷 Book wine tours in advance, especially during peak season, to ensure you get a spot.
•⛰️ Check the weather before heading up San Cristóbal Hill. The views are best on a clear day.
•🗺️ Be open to spontaneity. Some of the best parts of Santiago are the ones you discover by accident.
See our other posts on Santiago here
