For the 50+ Traveler

Valparaiso, Chile, is a lively, artsy port city full of history and colorful houses clinging to cliffsides. If that sounds appealing, make the one-and-a-half-hour trip west of Santiago to the Pacific Coast and spend at least one day in the city, which is a UNESCO World Heritage site.

Valparaiso’s bohemian vibe, hilly neighborhoods, majestic views over the bay, historic funiculars, and spectacular street art will have you under its spell in no time. No wonder its nickname is the Jewel of the Pacific. Here’s how to spend the perfect day in hip Valparaiso, Chile.

A street in Valparaiso, Chile.

Take A Free Walking Tour

Taking a walking tour is a fabulous way to get acquainted with any new city in a short time. Valparaiso is very hilly, so bring comfortable walking shoes and water and prepare to explore the warren of streets that make up this city.

There are two free walking tours that I can recommend. Both hold a morning and an afternoon walking tour. Both these tours will acquaint you with the highlights of Valparaiso.

The first is Free Walking Tour Valparaiso This walking tour is a brilliant combination of historical facts and architecture, vistas over the ocean, and riding the funiculars to get from one hillside neighborhood to another.

The second tour that I highly recommend is Valpo Street Art Tours. This walking tour also leads you through the tiny alleys of Valparaiso and up and down the hills. The focus is on the history and background stories of the local street art and artists.

Although the tours are technically free, if you enjoyed yourself and the guide, please tip generously.

A funicular in Valparaiso, Chile.

Ride The Funiculars

Valparaiso and its 42 hills can leave you a little breathless. Don’t worry, there are 15 funiculars that will ensure you still have some energy to explore the city. The funiculars, declared National Historical Monuments, are all more than 100 years old. Many are under renovation, but the seven working ones will get you where you are going in no time! In Valparaiso, the funiculars are called ascensores. Riding one of these is a must-do experience!

Make sure you have some spare change in your pocket as the ride will cost between 100 and 300 pesos (or 10 and 30 cents USD)

Be sure to ride these two ascensores during your time in Valparaiso:

Ascensor Reina Victoria

Ascensor Reina Victoria, built in 1902, has the steepest ascent and delivers you right in between Cerro Alegre and Cerro Concepcion.

Ascensor Concepcion

Ascensor Concepcion is the oldest of all the funiculars, hailing from 1883.

The Concepcion and Alegre neighborhoods in Valparaiso.

Stroll Through Cerro Concepcion And Cerro Alegre

When you spend a day in Valparaiso, you will become familiar with the Spanish word cerro. The cerro, meaning hill, is one of the defining characteristics of Valparaiso. Valparaiso is made of approximately 42 hills, most of which have communities built on them.

You could spend a good portion of the day ambling in Cerro Concepcion and Cerro Alegre. These two neighborhoods are full of ambience, promenades, and sweeping views over the bay. There are plenty of restaurants, coffee shops, and boutiques to enjoy as you meander along the tiny streets. Vendors are stationed in front of colorful houses selling handmade artisan goods, and the astounding street art makes for magnificent photo opportunities. Stroll along with a backdrop of chiming church bells and find Cafe Turri to enjoy a pisco sour and a meal with magnificent views. Why not aim for sunset?

Pablo Neruda's house at La Sebastiana.

Visit La Sebastiana, The Museum Of Pablo Neruda

Pablo Neruda is one of the most famous Chileans. The Nobel-prize winning poet had three homes in Chile. La Sebastiana in Valparaiso is a narrow five-story home with spectacular views over the Pacific Ocean, which provided Neruda with the perfect place for writing. His house was ransacked after the military coup in 1973 but restored in 1991. It is now a museum honoring the poet and full of his treasures and knick-knacks.

Note that the museum is closed on Mondays.

The harbor in Valparaiso, Chile.

Take A Harbor Tour

Valparaiso has a bustling port full of international freighters being loaded with shipping containers. It is not hard to pass time watching all the activity going on. Cranes are whirring. Ships are coming and going. If you want to get up close to the action, walk down to the port and take a boat tour. There are 30-minute tours during which you are sure to pass by sea lions and through the shadow of a massive ship or two. Looking back at Valparaiso and her colorful houses tumbling down the cliffs gives you another perspective of this historic city. In the evening, the 42 hills of Valparaiso come alive with the glowing twinkle of lights.

A pastel de choclo from Chile.

Eating And Drinking In Valparaiso, Chile

Chile is the land of empanadas, seafood, and the classic pastel de choclo: a meat pie with a filling that contains either beef or chicken, raisins, olives, and a hard-boiled egg. The dish is topped with mashed grilled corn that caramelizes in the oven. Try it. It’s rather delicious and reminiscent of shepherd’s pie. Not a meat lover? You could also try pastel de jaiba, a delicious crab casserole with cheese.

On any visit to Chile, there are two drinks to try, aside from savoring the local wines: the pisco sour and the terremoto. The classic pisco sour is created with Chilean pisco brandy, lemon, sugar, and ice. It makes for a delicious aperitif! I was never brave enough to sample the terremoto, as its name means earthquake. As a local explained to me, after drinking one of these, your legs will be shaking as if there’s been an earthquake. Somehow the combination of pineapple ice cream, grenadine, and a sweet white wine called pipeno can have that effect!

Cafe Turri

Cafe Turri in Cerro Concepcion is the perfect spot for a sumptuous seafood lunch overlooking the bay. Ask to sit outside on the terrace and be sure to request a table with a view.

Delicias Express

Delicias Express at Urriola 358 serves the best empanadas around, and what a variety to choose from -- 81 in all! This is a quick place to pick up a snack and eat it on the run.

El Pimenton

El Pimenton at Av. Ecuador 27, was recommended to me by a Valparaiso resident as a local restaurant serving authentic, homemade Chilean food. The pastel de choclo, that notorious meat pie, was sizzling and delicious. Also recommended was chorrillana: french fries covered in meat, fried eggs, and caramelized onions.

Want more inspiration? Read up on the best local dishes to try in Peru.

Emporio La Rosa

Emporio La Rosa, found at Plaza Anibal Pinto 1185, is the perfect place for an ice cream. Plaza Anibal Pinto is the meeting place for the walking tours, so take the opportunity to indulge in a cone at their sidewalk cafe either before or after your tour. How about trying a flavor you’ve never had before such as lucuma, made with a South American caramel-flavored fruit?

Souvenir prints from Hiperfocal Fotografia Taller Galeria.

Shopping In Valparaiso, Chile

There are plenty of boutiques to browse in Cerro Concepcion and Cerro Alegre. Be on the lookout for silver jewelry and lapis lazuli, which make for a stunning combination.

Bahia Utopica (Av. Almirante Montt 372) makes the perfect spot for browsing and finding authentic souvenirs.

For unique photographic prints visit Hiperfocal Fotografia Taller Galeria (Lautaro Rosas 392), where photographer Alberto Lagos sells black-and-white images printed on fabric.

Where To Stay In Valparaiso, Chile

If you decide that you would like to stay overnight in Valparaiso, opting for a spot right in the heart of the city, either in Cerro Concepcion or Cerro Alegre, is recommended.

Puerta Escondida Bed And Breakfast

Puerta Escondida Bed and Breakfast is in an early 20th-century home and has lovely rooms and welcoming and helpful staff. It is in the perfect location for exploring Valparaiso.

Casa Galos Hotel And Lofts

Casa Galos Hotel and Lofts, located in Cerro Alegre, comes highly recommended.

WineBox Valparaiso

Looking for a truly unique experience? WineBox Valparaiso is one of the world’s few hotels built from shipping containers and 75 percent recycled materials. Every single room has an amazing sea view. WineBox Valparaiso is located in Cerro Mariposa, walking distance from Cerro Alegre.

A local told me, “It’s obligatory as a tourist to leave Valparaiso with sore legs from all the hillwalking.” I would have to concur. Climb the hidden stairways, find the breathtaking views, and leave Valparaiso with tired legs and a heart happy that you ventured to this bohemian city.