Travelzoo Best Bets: Where to Go in 2026 with Chile Travel

A country this slender shouldn’t hold so much, yet Chile layers entire worlds end to end: a cosmopolitan capital set against the Andes, a desert where the night sky feels close enough to touch, vast Patagonian parks that safeguard wild silence, and a Pacific island where living tradition matters more than spectacle. In episode nine of our 10-part Travelzoo Best Bets Series, Dan and Travelzoo Senior Editor and co-host Gabe Saglie sit down with Jessica Canelo, Marketing Director at Chile Travel, to map a clear, inspiring path for traveling Chile in 2026. From what to see first and how to move smartly between regions to why community-led sustainability underpins every decision, this conversation brings Chile into focus.

We begin in Santiago, a city in the midst of reinvention. Walkable neighborhoods like Barrio Italia invite long meals and late nights, while the historic funicular to Cerro San Cristóbal delivers sweeping views that seamlessly link city and mountains. From the capital, Chile opens outward with ease. Nearby wine valleys Maipo, Colchagua, Casablanca, and Leyda tell a layered wine story, from benchmark cabernets to crisp coastal whites and the revival of heritage grapes like país and cinsault. Carmenere, once mistaken for merlot, now stands proudly as Chile’s signature, perfectly paired with smoky asados and Pacific seafood.