From Santiago, take Route 68 as it wanders northwest to the coast. In the heart of the Casablanca Valley, visit a boutique winery nestled in a cold corner with a unique microclimate. First, saddle up with the resident arriero, horseman, and giddy up into the vineyard for a close-up view of the vines. After, meet the resident sommelier to visit this family-run operation that ventured into experimenting with cooler grape varieties Cabernet Franc, and Northern Rhone-style Syrah. Tour the eco-friendly gravity-flow winery followed by a tasting of their finest wines.
Next, visit a small winery tucked in the western corner of the valley on the eucalyptus-peppered hillsides. Here, they excel at making a limited amount of lip-smacking Sauvignon Blanc, satiny Pinot Noir, and electric Northern Rhone-style Syrah. Tap into their passion on the visit with the winemaker and sit down to a tasting of their top wines with a sweeping view of the valley.
Take a lunch break in the town at a favorite local restaurant. The short-but-sweet menu focuses on regional dishes sourced by artisan producers and sustainable meats and fish, in simple, savory combinations paired with fresh ingredients and valley wines.
Overnight in the Rosario Valley, a stone’s throw from the coast. Settle into the century-old guesthouse, which hints of another era with the tasteful décor and a homey ambience. Explore on bikes or simply relax. Tonight, dine in their restaurant. (Matetic Vineyards La Casona)
This morning after a hearty country breakfast, visit a chic winery with a stunning location: its own 25,000-acre valley. Snake through miles of eucalyptus and native pines as the rolling hills gradually reveal the organic slope-planted vineyards. Visit the winery and sit down to a tasting of selected premium wines.
Next stop is a family-run project with breezy, hill-planted vineyards producing Chile’s finest Sauvignon Blanc. The passion and lifelong dream of the owner, the experiment with cool-weather grapes like Sauvignon Blanc, Pinot Noir, and lesser-known whites yielded palate-tingling results. Visit the property with the family and sit down to a tasting of their single vineyard Pinot Noir and Sauvignon Blanc.
Lunch is nearby at a local oceanfront seafood haven where they serve up the catch-of-the-day like sea bass or sweet razor clams. Watch the waves crash on the beach below. Savor another zingy Sauvignon Blanc from one of our favorite regional producers.
Transfer to Valparaiso and check into your hotel in the heart of the UNESCO world heritage site. Overlooking the azure Pacific, this gorgeous 1920s Victorian mansion has a bird’s eye view of the busy port below and colorful hills with colorful, zinc-sided homes seemingly built on top of each other. As night falls, the hills twinkle. Enjoy your dinner in the hotel’s gourmet restaurant. (Casa Higueras)
This morning, take the pulse of Valparaíso and its turn-of-the-century hills on a historical walk. Check out cozy cafés, old-fashioned mom-and-pop shops, and ride the city’s emblematic ascensores, funicular elevators dating back more than 100 years. Drive by busy plazas where children play and eat churros. Stop into the centuries-old market where vendors hawk the freshest daily produce, tangy goat cheese, briny olives, and lots of cheery banter. Valparaíso feels like a time warp—combined with a bohemian vibe and lots of personality.
Drive up the coast through Viña del Mar, stopping in the seaside village of Con Con to munch on the best seafood empanadas in Chile. Every morning, circles of fresh dough are rolled and stuffed with fillings like melted cheese paired with fresh abalones or velvety crabmeat. Try the classic mariscos empanada, stuffed with a medley of shellfish meat in a white wine reduction.
Continue up the coast to lunch in a scenic beach village with cliffs, golden sand, and turquoise waters. You almost feel like you’re on the Riviera—Chile’s version, that is. Dine at a local favorite spot with a wide variety of fresh seafood, rock fish, attentive service, views overlooking the surf, and more delicious wine. Return to Valparaíso in the late afternoon. Tonight, dine at one of the city’s top tables just a few blocks from your hotel. (Casa Higueras)
Take this morning at a leisurely pace with a late checkout to relax by the poolside, linger over an extended lunch or visit poet Pablo Neruda’s museum on nearby Cerro Bellavista. Meet your English-speaking driver in the late afternoon and transfer back to Santiago, or the international airport. Tchau amigos.