Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
In port at Santiago, the bucket-list move is Private Santiago City Highlights with Expert Local Guide. ToursByLocals – Private Santiago Guides runs it — a private, expert-led experience at your own pace, not a 40-person coach. Below: all 6 bucket-list things to do on a Santiago port day, each with the independent way to make it yours.
1culture
A bespoke, chauffeured private tour of Santiago's most iconic landmarks — Plaza de Armas, Cerro San Cristóbal, Bellavista & La Moneda — curated entirely around your pace and passions. This is Santiago distilled to its finest, with no crowds, no rushing, and a vetted local expert who knows every hidden corner.
Book it withToursByLocals – Private Santiago GuidesFrom USD 380 per group (private, up to 4 guests)
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2food
Journey into Chile's most celebrated wine valley for an exclusive estate visit, barrel-room tour and sommelier-led tasting of premium Carménère and Cabernet at one of Maipo's legendary bodegas — paired with a refined lunch. This is Chilean viticulture at its most aristocratic.
Book it withViña Santa Rita (Official Estate)From CLP 35,000 (approx. USD 38) for standard tasting; private premium experiences from USD 120 per person
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3culture
Valparaíso's labyrinthine hillside neighbourhoods, UNESCO-listed historic quarter and world-famous open-air murals are best navigated with a private local guide who can decode every painted alley and Victorian mansion. Ride the legendary Ascensor Concepción and sip cortado in a clifftop café with infinite Pacific views.
Book it withGoWithGuide – Valparaíso Private ToursFrom USD 380 per group (private, up to 4 guests)
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4scenic
Follow the Maipo River deep into the Andes along one of South America's most dramatic canyon roads, culminating at the impossibly turquoise El Yeso Reservoir at 2,500 m elevation. This private full-day adventure delivers Patagonia-calibre landscapes without a flight — just raw Andean grandeur at your fingertips.
Book it withCascada Expediciones (Official)From USD 180 per person (private day tour)
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5landmark
Ascend Santiago's beloved Cerro San Cristóbal aboard its 1925 funicular railway to the summit statue of the Virgin Mary, where the entire city spreads below and the snow-capped Andes fill the horizon. Time it for golden hour and toast with a perfectly made pisco sour at the hillside terrace bar.
Book it withTeleférico Cerro San Cristóbal (Official – Parque Metropolitano de Santiago)CLP 3,400 (approx. USD 3.50) funicular round-trip; terrace bar drinks from CLP 8,000 (approx. USD 8)
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6adventure
Drive the spectacular Ruta 60 through the High Andes to the legendary Portillo ski resort and the Argentine border at 3,832 m — a road-trip through snow tunnels, switchback hairpins and glacier-carved valleys that rivals any mountain drive on earth. Out of ski season, you'll have the epic landscape virtually to yourself.
Book it withCascada Expediciones (Official)From USD 220 per person (private Andes full-day tour)
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