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One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.

Frank Altamura took his time renovating the old Italian grocery store — where he remembers shopping as a child — at the north end of Yountville. His dream was to turn the partly dilapidated building into a casual restaurant with great pizza and Napa Valley wine where locals would love to eat. His dream came to fruition when Ciccio opened its doors in 2013. The menu is simple, straightforward and ever-changing based on what Altamura is bringing in from his Napa ranch, where he also grows Cabernet Sauvignon, Nebbiolo, Sangiovese and Negroamaro for his eponymous wine. Chef Polly Lappetito (former Executive Chef at The Culinary Institute of America) traveled far and wide in search of the perfect pizza crust, but her’s is in a category all its own — prepared in a hand-tiled, wood-burning pizza oven imported from Italy.

The weekly flohmarkt (flea market) in Friedrichshain’s Boxhagener Platz is a popular spot where locals meet up for shopping, drinking, or just a bit of fun each Sunday. While the Mauer Park flea market gets most of the tourists, this one is far less touristy. You’re much more likely to find a good deal on used books, cool T-shirts (some by local designers, even!), music records, and knickknacks. Because the market is relatively small, it’s quite enjoyable to take a stroll through the stalls and then enjoy a picnic on the grassy area in the middle of the square. Many cafes and restaurants are situated on the streets bordering Boxhagener Platz so you won’t be bored for things to do. The market is open Sundays during daylight. On Saturdays in the same area you’ll find a fresh food & produce market.

For the past 10 years, Mario, the owner of VEBorange, has been selling DDR (East Germany) collectables and other German antiques. Most items in the shop on Oderberger Strasse are objects made and sold between 1950 and 1980, making this a great place to find kitschy and totally unique goods. When I visited on a sunny Saturday afternoon, Mario was tinkering with a Sputnik relic from the CCCP. Not everything that he collects or receives ends up on the shelves. Behind the counter are the things deemed interesting or noteworthy—things that might fit in a museum. If the nearby Mauer Park turns out to be too disappointing for you, head over to VEBorange (a short three-minute walk away) to find truly unique and special items. You can find everything from old Soviet war medals to clothes and furniture.

Castle Ho’s motto, the owner of lovely boutique 1861, is quite simple. “Women who love being women and dressing the part.” Such is the premise of her work, and it definitely transposes into her boutique. The store is decorated in what seems to be a vintage fashionista’s dream: airy space, high ceilings,Vvictorian inspiration, and soft eggshell, champagne and pastel pink hues everywhere. No boys allowed! The multi-brand store focuses on feminine, timeless pieces first and foremost, and incorporates up-and-coming designers into the mix, like UK-based Emily and Finn and Torontonians Pink Martini, along with Montrealers lines Coccolily and Arti Gogna. Don’t be fooled by the perfect, fairy-tale decor; the prices are more than fair and very few things are over $100 in the store. Guilt-free, stylish shopping? I like.

RedRocks is a small eatery in the Columbia Heights neighborhood in Washington, D.C. It’s located just a couple blocks off the main commercial area hugging 14th Street. While there are plenty of chain restaurants peppering 14th Street, it’s worth straying a couple blocks to come to RedRocks. This is a neighborhood bistro that’s all about casual dining—perfect for unwinding from a day of sightseeing or shopping along 14th. Neither the atmosphere nor the food is pretentious. I come for the wood-fired pizza, and nothing satisfies me more than their Neapolitan pizza topped with house-cured sausage and pepperoni. You can come here with friends and just hang out to eat and drink and have a good. Sometimes simple pleasures are the best! Metro stop: Columbia Heights

Not just a wonderfully large bookstore—although it is that—the University Bookstore is also a café and a fantastic gift shop. The two-level bookstore has a textbook section for students and general fiction and nonfiction for the public, as well as a good selection of art supplies and kids’ crafts and toys downstairs. The large front room is devoted to all things fun: journals and stationery, makeup counters, bags and silver jewelry, candy and novelty items, soaps and housewares. If you’re a Husky fan, they have plenty of team merchandise, too. The Seattle bookstore has frequent author reading events (shown above: a cupcake-loving dragon sketched by illustrator Jackie Morris during a Robin Hobb reading), so check their calendar and see what’s going on while you’re in town.

The Bonsecours Market is hard to miss, whether you are walking around Montréal’s historic center or looking at the skyline from the harbor. A silver dome caps the long building, which dates from 1844 and was modeled on Dublin’s Customs House. It looks more like a stately civic building than a market, and in fact it was Montréal’s city hall for a while, as well as the seat of Canada‘s parliament for one session. After serving as the central market of the city for nearly a century, it closed in 1963 and was largely abandoned until 1992, when it reopened as the home of a visitors’ center for Montréal’s 350th anniversary. Today it houses a dozen or so boutiques featuring works by local designers, as well as a few restaurants that make for good pit stops on a day of sightseeing.

Since opening as a preserves shop in 2011 (and adding breakfast and lunch service in 2012), Sqirl has become an East Hollywood staple. The tiny space—only 800 square feet—invites crowds of hip Angelenos looking for a bright space for all-day breakfast and brunch that’s carnivore-, vegetarian-, and vegan-friendly. There’s an airy outdoor patio where diners can take in the L.A. sun and sip on the fresh-squeezed juice of the day while ruminating over the eclectic menu. The buckwheat pancakes make for a great healthy unhealthy breakfast: They’re made with buckwheat and cactus flour, cocoa nibs, and toasted coconut, making them vegan, gluten-free, and not-so-sinfully delicious.

Just across from the bus station in Belmopan, on Market Square, is the welcoming Caladium Restaurant. Serving locals and visitors since 1984, it was the first dining room in town to offer take-out service. The main room is adjacent to a gift shop where traditional Belizean art and crafts are for sale. The menu favors local dishes such as chicken with rice and beans but international options like sweet and sour pork are also available. Fresh-squeezed juices from watermelon, tamarind and papaya are available, as are imported beers and soda. I was glad I saved room for the flan, which was perfectly balanced with a caramel sauce tinged with just a hint of liquor. Breakfast is served in the morning beginning at 7 a.m. and lunch is available from 11 a.m. until 8 p.m., Monday through Saturday.

Located on seven-mile-long Estero Island, Fort Myers Beach is precisely the sugar-sand playground you come to Florida’s Gulf Coast to enjoy. Named among the best in America, the beach is long and wide, making it perfect for a stroll or bike ride—especially at low tide. Vendors here sell everything from umbrella and chair rentals to parasailing adventures and eco tours. There are also accommodations, including hotels, inns, and small, family-run motels to fit nearly every budget.

Head to the Gothic Quarter—once home to Barcelona‘s storied Jewish neighborhood, El Call—and look for the Sinagoga Major (Major Synagogue). The museum, built on the site of the city’s oldest temple, is only two rooms, but it contains a stadium’s worth of history. For just 2 euros, you’ll get a tour of the excavation site and a riveting tale of the Jewish faith in Spain—plus an entertaining ancedote about how the ruins were discovered. Nearby, you can sign up for a guided tour of El Call, or shop for books and kosher products at the Barcelona Call Store. The synagogue is open Monday through Friday from 10:30 a.m. to 5:30 p.m. and Saturday and Sunday from 10:30 a.m. to 2:30 p.m.

For a taste of the good life, head to South Beach, known for its Art Deco hotels lining Ocean Drive and Collins Avenue, glittering nightlife, and see-and-be-seen vibe. The long stretch of beach, starting with the pier at the top of historic Washington Avenue, is a great place to take in the Miami of postcards and enjoy the sunset over the cityscape. This is where you’ll find some of Miami’s best shopping, top-tier nightlife, and award-winning restaurants, not to mention great people-watching and luxury-car spotting.

Though from Guadalajara (he never let friends forget), Pritzker Prize–winning architect Luis Barragán lived much of his life in Mexico City, where he designed and constructed this, his last residence, completed in 1948. A UNESCO World Heritage site, the home is open to be toured by small groups—by appointment only; English-language guides are available upon request—who want a chance to tap into Barragán’s brand of minimalism, which involved bold monochromism and a masterful use of light; striking horizontality and framing applied to windows, gardens, and views; a highly sui generis Catholic spirituality; and, not least of all, the architect’s bizarre need for control, in everything from what staircases guests might use to what records got played in different rooms.

The Art is a worthy base for those looking to explore the galleries of the Denver Art Museum, the Clyfford Still Museum, and the Kirkland Museum of Fine and Decorative Arts, which are all within a few minutes’ walking distance. In fact, the glass-walled property feels a bit like an exhibition space in its own right: Upon arrival, guests are greeted by Leo Villareal’s dazzling 22,000 LED–bulb installation above the entrance, while hundreds of other works by the likes of Frank Gehry appear throughout the public spaces—see them on a guided tour of the hotel’s art collection, offered on Saturdays. Minimal guest rooms have light wood furnishings, luxury linens, and neutral walls—the better to serve as a blank canvas for more original artwork—as well as windows overlooking the mountains or city lights. If you’ve worked up an appetite with all that cultural appreciation, order the signature burger with spicy mayo at FIRE restaurant, or sip a Matisse martini with Colorado-made vodka on the fire pit–warmed terrace.