Two-Week Best of Chile Itinerary

Chile’s sinewy length is matched by a wealth of places to visit. It’s no mean feat to pack in the country’s highlights in a two-week trip. Stand in awe of some of its most jaw-dropping landscapes and remotest national parks while soaking up history and culture. This itinerary is selective and fast-paced. It requires a number of domestic flights to cover the necessary long distances between attractions.


Day 1

Arrive in the morning into Santiago’s Aeropuerto Internacional Arturo Merino Benítez and take a taxi to the city center. Drop your luggage at the stylish boutique hotel The Aubrey, in the heart of Barrio Bellavista.

aerial views of top of Cerro Santa Lucía
Views on top of Cerro Santa Lucía. Photo © Diego Grandi/

In the vibrant Barrio Lastarria, take the paved path to the top of Cerro Santa Lucía for dazzling panoramas across the city to the mountains beyond.

Head to the Plaza de Armas, Santiago’s main square. Visit the 18th-century Catedral Metropolitana before spending an hour or so in the superb Museo Chileno de Arte Precolombino, exploring the underground room dedicated to pre-Colombian Chilean textiles, ceramics, and religious artifacts.

For dinner, get acquainted with the country’s diverse organic wines and creatively plated Chilean dishes at Polvo Bar de Vinos.

Valparaíso and Valle de Casablanca

Day 2

Take the 1.5-hour bus ride west to the wine region of Valle de Casablanca and rent a taxi to take you around the nearby wineries. Drop in for a tasting and vineyard tour at Viñamar and Emiliana, then have lunch at Tanino, the on-site restaurant at Casas del Bosque.

Hop back on the public bus; it’s an hour-long journey to Valparaíso, where you can stay the night in Winebox, a hotel owned by the former winemaker of Casas del Bosque.

Day 3

Start early for the 1.5-hour bus ride to Casa Museo Isla Negra, the sea-inspired home of poet Pablo Neruda, south of the city. Dine on baked parmesan razor clams at the museum’s restaurant, El Rincón del Poeta, before returning to Valparaíso.

Spend the afternoon visiting viewpoints in the graffiti-daubed hills of Cerro Alegre. Pop into the Museo Municipal de Bellas Artes for a history lesson about the city. Be sure to ride on a couple of the creaky ascensores, historic funiculars that transport passengers up the city’s steep hills.

view of Puerto Natales with a building in the distant, flowers, and crystal blue waters
Puerto Natales. Photo © Emicristea/

Southern Patagonia

Day 4

Catch the bus to the Santiago airport and take an early-morning flight to Aeropuerto Internacional Presidente Carlos Ibáñez del Campo (3.5 hours), the main airport in Patagonia. From the airport, a bus (3.25 hours) runs north to Puerto Natales, where you can wander among historic weatherworn buildings and watch birds from the banks of the mountain-fringed sound on which the town is situated. Note that it’s possible to fly directly to Puerto Natales from Santiago during high season. This will allow enough time for a half-day horseback tour at a nearby ranch.

Rent a car for the following day’s drive. Have dinner at the innovative Lenga (make a reservation ahead of time) before getting a good night’s sleep in elegant VinnHaus.

Day 5

Leave early for the 2.5-hour drive to the southern entrance of Parque Nacional Torres del Paine. Take a three-hour boat tour with Turismo Lago Grey to the snout of the dazzling Glaciar Grey.

Have dinner at Hotel Lago Grey, where you’ll get views of bobbing icebergs on the lake. This is also a good spot to spend the night.

Day 6

From your hotel, take the road through the national park to the Centro de Bienvenida. From here, take the trail to Mirador Las Torres (15km round-trip, 4 hours), a viewpoint of the park’s eponymous towers. It’s a steep climb up a rocky valley to reach the lake and granite peaks. Return the way you came.

Drive back to Puerto Natales. Treat yourself with a night in the gorgeous fjord-side hotel Simple Patagonia. Dine next door in The Singular Patagonia, with its lavish wine menu and gourmet Patagonian-inspired cuisine.

View of Glaciar Perito Moreno with fall trees
Glaciar Perito Moreno. Photo © Saiko3p/

Day 7

It’s time to visit Argentinean Patagonia. Board a bus (5hr) for El Calafate, Argentina. Continue on to Parque Nacional Los Glaciares, 1.5 hours by bus from El Calafate. In this park of extreme contrasts, you can get within a few hundred meters of Glaciar Perito Moreno, one of only three glaciers in the world that’s growing.

When you get back to El Calafate, dine on steak and sip malbec at classy La Zaina before spending the night at the quirky Patagonia Rebelde or the friendly midrange Kau Yatún.

Day 8

Return to Puerto Natales by bus (5-8 hours). Transfer to a Punta Arenas-bound bus (3.25 hours). Once you arrive in Punta Arenas, try the king crab at the beautifully situated La Yegua Loca, which is also an inn. Spend the night here or at the affordable Hotel Lacolet.

Day 9

From Punta Arenas, it’s possible to take a day tour of two different penguin colonies. The closer of the two is the Monumento Natural Los Pingüinos on Isla Magdalena. After a ferry or speedboat ride, you’ll disembark on an island occupied by thousands of chattering Magellanic penguins.

The other option is to take a tour from Punta Arenas to the Parque Pingüino Rey, in Tierra del Fuego. This private reserve protects a small colony of king penguins—the only colony in the Americas.

Day 10

Visit the Museo Regional de Magallanes to learn about a prominent Punta Arenas wool merchant family. Wander the promenade that parallels the Strait of Magellan for potential dolphin sightings.

Take an afternoon flight to Puerto Montt (2.25hr), then transfer from the airport to lakeside Puerto Varas, just 20 minutes away. Dine at La Olla for a feast of traditional Chilean seafood and stay overnight at hostel Compass del Sur to best appreciate the town’s homespun charm.

View of Lago Todos Los Santos in Parque Nacional Vicente Pérez Rosales with crystal blue waters, and vibrant green trees.
Lago Todos Los Santos in Parque Nacional Vicente Pérez Rosales. Photo © Hugoht/

Lakes District

Day 11

Rent a car in Puerto Varas and drive an hour to Lago Todos Los Santos in Parque Nacional Vicente Pérez Rosales. Check out the superb on-site museum, then take a short wander along the lake’s black-sand beach. On your way out of the park, stop to take in views of the majestic Saltos del Petrohué waterfalls.

On the road back to Puerto Varas, stop at the boutique hotel AWA and treat yourself with gourmet dining and a luxurious stay on the shores of Lago Llanquihue.

Day 12

Rise early and return to Puerto Varas, where you can either drive or rent a bike and pedal north around the lake to quaint Frutillar. Catch a show at the glorious Teatro del Lago followed by afternoon tea overlooking the lavender fields at Lavanda Casa de Té.

Back in Puerto Varas, enjoy Patagonian craft beer and pizza with exquisite lake views at La Mesa Tropera. Check into a lodging in town and get a good night’s rest.

Day 13

Catch a bus north to Pucón (5hr) and spend the afternoon sunbathing on the black volcanic sand of Playa Grande or relaxing in the hot spring water of the Japanese-inspired Termas Geométricas. You may feel like you’re in Europe thanks to the authentic Italian dishes at Andiamo. Bed down for an early night in one of the cozy hobbit holes at Chili Kiwi.

View of Volcán Villarrica with clear water and a golden tree on the side.
Volcán Villarrica. Photo © Brizardh/

Day 14

Wake before dawn for the challenging full-day ascent of Volcán Villarrica. Alternatively, catch a bus to Parque Nacional Huerquehue for a gentler hike along one of the park’s trails.

Return to Pucón and toast your Chilean adventures with Mapuche-inspired dishes at La Fleur de Sel and a night at Maison Nomade B&B, with its startling volcano views. In the morning, you’ll fly to Santiago, then back home.

Steph Dyson

About the Author

From hitchhiking along the Carretera Austral to sailing to the very ends of the earth in Tierra del Fuego, Steph Dyson has made it her mission to explore every nook and cranny of the thin, sinewy country that is Chile.

Arriving in Chile in 2016 after a year and a half of exploring South America, Steph discovered that Patagonia, despite its sheer mountains, plunging river valleys, and glaciers, felt a bit like home back in the UK (it was raining, mostly). Further north and able to recognize a good thing when she found it, including a city brimming with book shops and wine bars, she swapped her rucksack and hiking boots for a flat in Santiago, where she continues her love affair with the country.

A full-time freelance travel writer, blogger and former high school English teacher from Bath, UK, she’s lived in three countries in South America and written about many more. A member of the British Guild of Travel Writers, she has published articles both online and in print for various regional and international outlets. Inexhaustibly itinerant, she spends most of her time on the road somewhere in South America, writing about her adventures on her travel blog, Worldly Adventurer.

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