The best way to explore Chile? On a road trip from Santiago to the port city of Valpraiso. Here are the essential stops.


Bocanáriz: With more than 300 wines (35 by the glass), the brick-walled bar—whose name means “mouth-nose”—has the country’s largest selection of Chilean varietals. Bilingual sommeliers will walk you through the list, and the food menu is divided into sections such as land and sea. 276 José Victorino Lastarria. $$

Centro Cultural Gabriela Mistral: The former headquarters of Pinochet’s military dictatorship has become Chile’s biggest cultural center, hosting theater and dance performances. Political photos by native son Claudio Pérez are now on view inside the sprawling copper fortress. 227 Avda. Libertador Bernardo O’Higgins.

Lastarria Boutique Hotel: For a quiet retreat in the boho Lastarria district, book one of the 14 antiques-filled rooms at this 1927 property. Our pick: the top-floor junior suites, with balconies big enough for loungers. Complimentary breakfast and afternoon tea—plus mote con huesillos (a drink of dried peaches, cinnamon, sugar, water, and husked wheat)—are served on the patio. 188 Coronel Santiago Bueras. $

Mulato: Cristián Correa’s cozy restaurant serves fresh Chilean dishes such as pan-roasted hake with lentils and clam sauce. Correa—who helped found a local brewery—shops daily at the farmers’ markets and incorporates red wine into his rustic walnut bread. 307 José Victorino Lastarria. $$

Santiago to Lagunillas

Drive Time: 1 hour, 20 minutes

Matetic Vineyards: This glass-walled winery is known for its pioneering Pinot Noirs, Syrahs, and Sauvignon Blancs made with biodynamic grapes. Its on-site, century-old estancia La Casona has seven wood-accented rooms with views of sloping vineyards and flower gardens. There’s also a pool and hiking, biking, and horseback-riding trails. Fundo El Rosario; includes some meals and activities. $$$$

Lagunillas to Lo Abarca

Drive Time: 20 minutes

Viña Casa Marin: Maria Luz Marin was told she was crazy when she planted vines just 2 1/2 miles from the Pacific Ocean. But despite cold fronts and strong winds, the family-run winery is producing top Sauvignon Blancs. If Marin isn’t there, her brother will give you a tour. Camino Lo Abarca.

Lo Abarca to Isla Negra

Drive Time: 30 minutes

Museum House Isla Negra: The tiny fishing village is home to Pablo Neruda’s quirky, mazelike residence. Built to resemble a ship, it’s filled with the poet laureate’s eccentric collections: tribal masks, ship figureheads, and sperm-whale teeth. Camino Vecinal.

Isla Negra to Valparaiso

Drive Time: 1 hour, 30 minutes

Fauna Hotel: With its reclaimed materials and thrift-store finds, the funky 15-room hotel is a more laid-back answer to nearby Hotel Palacio Astoreca. Take in sweeping vistas of the ocean from the outsize terrace—with a pisco sour, the national drink, in hand. 166 Pasaje Dimalow. $

Hotel Palacio Astoreca: This cherry-red-and-white 1923 mansion is the city’s premier boutique hotel, mixing original details (crown moldings; parquet floors) with modern pieces. El Bulli alum Francisco Araya heads up the seafood-focused Alegre. 149 Calle Montealegre. $$

Parque Cultural de Valparaiso: After a $14.5 million revamp, an old prison has been transformed into a sprawling public park and multi-venue cultural center. A café and shops are on the way. 471 Calle Cárcel.

T+L Tips: Make sure to have plenty of pesos on hand: Chile’s highways are excellent, but you’ll pay for their upkeep at regular tollbooths (around $7 for this drive). Also: Valparaiso’s steep hills can be tricky to navigate, so consider requesting an automatic rental car.

Appeared as "A Slow Rroad Through Chile" in T+L Magazine