“Valparaíso, what an absurdity you are,” wrote the poet Pablo Neruda in his ode to the city he occasionally called home. “What a head of disheveled hills, that you never finish combing.” While the hills and sea views are the city’s most marked natural features, it’s the profusion of brightly colored buildings smashed alongside each other, ambling for those views with dramatic funiculars, that make Valparaíso so special — and a must-stop on any trip to Chile.

Most tourists to the nation will likely center their journey around the capital, Santiago. But just two hours away, near the beach and with a twin city in the resort town of Viña del Mar next door, Valparaíso is the cultural heart of Chile. A visit to the South American country wouldn’t be complete without a visit to this seaside area, important both in Chilean culture as well as internationally due to its history as the major port linking the Pacific and Atlantic oceans before the Panama Canal was created; UNESCO first designated the city’s historic center in 2003.

With history, art, food, and a great beach for swimming, everyone can find something to do in Valparaíso and Viña del Mar. Here are some places to start.

When to Go

Chile is, of course, in the southern hemisphere—so their seasons are reversed. Still, temperatures are moderate year-round, hovering in the 40s to 60s even in the depths of summer and winter. The warmest season for enjoying Valparaíso’s sea breezes or Viña del Mar’s beaches is December through March.

What to Do

Take a street-art tour.

Aside from houses awash in apple green, purple, and Pepto pink, the historic center of Valparaíso is chock a block with murals and art installations. You could explore on your own (and fill your camera roll with this animated charm) or grab a guide. Valpo Street Art Tours offers eight different tours, including one where participants can spray their own graffiti and that’s tip-based, aka otherwise free. Similar tours are also available through Airbnb’s “experiences” offerings in the city.

Valparaiso
Kaitlin Menza

Ride the funiculars.

The city’s dramatic hills can be climbed on foot or enjoyed via funicular. The railways — called ascensores, or elevators in Spanish, though they’re not strictly vertical — dotted the port city at its commercial peak during the turn of the 20th century but have fallen into disrepair, with only a handful still functioning. Climb aboard one of these rickety things for the history, but also because it’s just convenient and cool and costs a few cents: El Peral, Artillería, and Concepción are popular choices.

Check out the flower clock.

Drive around Viña del Mar for five minutes and you’re likely to pass the flower clock, Reloj de Flores, which was created for the World Cup in 1962. Three arms spin around the bright red and pink flowers that make up the clock face, making for a kind of corny but rather pretty tourist attraction.

Go to the beach.

The twin cities’ dramatic views can only be enjoyed for so long before you start pining for the sand. The hottest beach in Viña del Mar is Reñaca, which is surrounded by restaurants and shops, and is known to be a bit of a scene. Slightly more relaxed is Playa del Sol, a long stretch that still has plenty of cafes and cocktail spots for sunset on the Pacific.

Visit La Sebastiana.

The poet Pablo Neruda, who won the Nobel Prize in 1972 shortly before his death, is one of the proudest figures in Chilean history, and his influence—and lovely word —can be spotted everywhere. He maintained three homes in Chile, all of which are now open to the public through the Fundación Pablo Neruda. His home in Valparaíso, dubbed La Sebastiana for the architect who created it, is a whimsical funhouse of carnival horses, colorful glass, and the cozy armchair from which he wrote. An excellent audio guide accompanies you on your visit, sharing humorous stories and explaining the provenance of interesting objects.

Where to Eat

Tres Peces
As the name suggests, this restaurant is focused on seafood — but also sustainability, as the owners are dedicated to responsible fishing and only serve what was caught that day. Photos of their fishermen as well as diagrams of the region’s fish decorate the walls of what was until recently a private home, and each main dish only costs about $11.

Tres Peces
Kaitlin Menza

Apice Cocina de Mar
One of the most romantic restaurants in the area, Apice offers fine dining of fresh seafood with an unbelievable view of Valparaíso’s port and the Pacific beyond. The tiny menu generally offers just two options per course, with ceviche, scallops, and hake as common options alongside a wine list by local producers.

Cafe Entre Cerros
This charming little spot is the essence of Valparaíso: a little ramshackle but packed with art, heart, and flavor. Exposed beams and a stairwell packed with paintings welcome guests, while the food gets them to stay: inventive sandwiches on homemade bread, fresh salads and fruit juices, chocolate-drizzled desserts, and a long list of interesting coffee drinks make it the perfect daytime stop.

Where to Stay

Sheraton Miramar and Convention Center
Jutting out on its own bluff so that every room feels like it’s floating out on the ocean is this five-star hotel, which boasts 138 rooms and a long history as the centerpiece of Viña del Mar’s resort life. Two restaurants (including a fine-dining option focused on seafood), a bar, two pools, and a spa entertain guests when they’re on the grounds, but the Miramar is also walking distance from many of the city’s biggest tourist attractions—and across the street from the Reloj de Flores.

Sheraton Miramar
Marriott

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Hotel Palacio Astoreca
With its unmissable cherry-red facade in the heart of Valparaíso’s historic center, this 1920s mansion was restored and reopened as a boutique hotel in 2012. The 23 rooms overlook the bay and have chic, minimalist interiors. Plus, the hotel boasts multiple fun extra areas to hang in, including a funky library, sprawling piano lounge, and a wine cellar.

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Casa Higueras
Another converted 1920s mansion, the feeling of Casa Higueras is warm and comfortable, with dark wood enveloping the walls, floors, and furniture. The Valparaíso hotel offers free guided tours of the city and cultural programming, including architectural visits, and the attached restaurant, Maralegre, has a grand terrace, as do many of the rooms.

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Kaitlin Menza

Kaitlin Menza is a freelance features writer. She lives in New York. You can see more of her writing at kaitlinmenza.com