Valparaíso is modern-day bohemia meets sun-drenched seaport, with a healthy dose of college life thrown in just for fun. It’s a unique blend of culture and coastal charm that earned the city the nickname “Jewel of the Pacific”.

The city is informally split into two parts: a flat expanse that leads in from the coast and a short way up the hillsides and the scenic, higher elevation neighborhoods. It’s no surprise, given the steep inclines that partially ring Valparaíso, that the city often draws comparisons to San Francisco, and there are some similarities with architecture and overall vibe as well.

Valparaíso is constantly changing, something the 300,000 or so locals seem to appreciate. Go for a visit, and the city just might change you, too.

Book a Room

Once upon a time, Casa Higueras was a private mansion, but these the 20-guestroom property caters to travelers looking for elegance, historic architecture, and an afternoon or two in the on-property spa. The building housing Fauna Hotel dates back to the late 1800s; the façade is largely original, but the rooms bridge the gap from vintage to modern with warm décor and unique murals created by some of Chile’s most notable artists.

If the city starts feeling a little congested, there’s plenty of peace and quiet to be had at Casadoca, a boutique hotel situated on the ocean about 25 minutes from Valparaíso. Rooms are luxuriously outfitted with everything from high thread-count sheets to LCD flat screen TVs with iPod connections, and some have private terraces with views of the sea or gardens.

Dine & Drink

If you’re working while traveling the globe, you’ll want to start your day (or pause for the afternoon) at Café Astillero, a WiFi-equipped spot that makes up for it’s petite size with monstrously good coffee.

Try Din_399, and innovative coworking space that doubles as a restaurant with Instagram-worthy dishes.

For lunch, try DIN_399, and innovative coworking space that doubles as a restaurant with Instagram-worthy dishes like Italian pumpkin noodles in pomodoro sauce and cold pea soup topped with salmon sashimi and pickled beets and radishes. Boliche Le Pato offers a quicker option: the most savory, flaky, mouthwatering delicious empanadas your mouth will ever be lucky enough to enjoy.

Splurge on dinner at Apice Cocina de Mar, where the French-trained owners turn local catch into masterpieces as beautiful as the restaurant’s ocean view.

See the Sights

Valparaíso’s historic quarter is a collection of five neighborhoods that include retail spots, cafes and restaurants, homes, museums, naval buildings, and public areas ideal for people watching. The area was named a UNESCO World Heritage site in 2003, and it’s well worth a wander, especially if you take the time to appreciate the abundant street art that helps make the quarter so vibrant.

Noted Chilean poet Pablo Neruda once lived in Valparaíso, and one of his abodes, La Sebastiana, has been restored and transformed into a living tribute to the artist’s life and work. The house itself is filled with fascinating details and carefully curated artifacts, but it’s hard to ignore the panoramic view – the reason Neruda bought the villa in the first place.

Sometimes it seems like everything in Valparaíso was once something else, and the Ex Carcel, also known as the Cultural Park of Valparaíso, is no exception. The complex started out as the city jail, then it was an artist commune, and now it’s a cultural center that hosts major events, rents out rehearsal spaces, and includes a public park.

Stop & Shop

Take home some of Valparaíso’s artistic spirit with pieces from Bahia Utopica, a gallery featuring work from some of Chile’s most buzzworthy painters, sculptors, and mixed-media visionaries. Contemporary design goes sustainable at Bazar la Pasión, a high-end retailed with pretty clothing, accessories, and other fun finds all produced with environmental awareness in mind.

One of the best ways to get a feel for Valparaíso is at one of the local markets. Vendors hawk an array of goodies ranging from fresh whole fish still dripping salty seawater to huge, juicy clusters of grapes grown just a short drive away.

What to Know Before You Go

The Best Way to Travel: To get to Valparaíso by air, you’ll have to fly into Santiago’s Arturo Merino Benitez International Airport. From there, you’ll need to hop on a bus (cash only, please) to Terminal Rodoviario Valparaíso, where you can hire a taxi to your final destination or make like a local and get a travel card for the city busses or commuter rail.

When to Go: Valparaíso boasts a temperate climate, with summers that rarely see temps above the lows 70s Fahrenheit and winter lows in the 50s. Remember, though, that this is the southern hemisphere, so the hot months are January, February, and March.

Local Currency: Chilean peso

Native Language: Spanish

Plan To: Conquer your fear of heights thanks to the city’s funiculars, which are essentially what happens when an elevator and an escalator have a baby. They may seem odd at first, but these boxy rides provide some of the most breathtaking views of Valparaíso.

Here’s a Hint: Leave your type-A tendencies at home. The best things in Valparaíso happen by accident. Make a plan to get there, then let the city take over.