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At Little Italy’s Herb & Wood, Chef Brian Malarkey’s wood-fired dishes include roasted parsnips with pickled raisins, parsley-shallot verde, and molten Marin County brie; roasted beets with sherry, walnut pesto, jamón Ibérico, and burrata; and grilled flat bread with whipped eggplant, za’atar, onions, and pine nuts. But the Mediterranean- and California-inspired menu isn’t the only big draw here: The industrial-boudoir aesthetic is equally inviting, with tufted sofas, soft lighting, and feathery fronds under the soaring ceilings of this onetime warehouse. A charmingly tattered edition of Emily Post’s Etiquette book has pride of place on the hostess stand. But the restaurant is unlikely to call guests on any manners infractions except one. In calligraphy at the bottom of the menu, you’ll find the following note: “Substitutions and additions politely declined.”

In the heart of El Viejo San Juan, the Plaza Colón (Columbus Plaza) is so much more than a place honoring an important piece of San Juan’s history. Sure, snapping an Instagram photo in front of the bronze statue of Christopher Columbus, credited for the first discovery of the island, is definitely a “must-do.” Find a local and in your best Spanish accent say “Perdón, podría tomar una foto por favor?” Or play it safe and ask another tourist in English (they’re not hard to find!). Either way, stay and hang out. Explore the local artists’ tents (like this one, with rings and bracelets made from brightly colored ceramic beads and recycled aluminum, customized to fit). Pick out unique, inexpensive gifts for loved ones and, of course, something to remember the trip! And don’t ignore the ringing bell of the sorbet vendors selling “coco frio” for $1. Try a scoop of papaya y piña to help cool off in the heat of the Puerto Rican sun.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

Montage is a hip, and highly curated collection of vintage men’s and women’s clothing, jewelry, and accessories, focused on the 1940’s through the 1990’s. The jewelry is particularly worthy of note, as much of their collection is made from broken or scrap pieces that have been reinvented and revitalized.

Most visitors never cross the river from the Old Part, and the vast majority overlook what has to be one of the most beautiful hikes from here to California. At the edge of Gros, a trail heads up some stairs (at the end of Calle San Francisco) and continues for hours, all the way to the neighboring village of Pasaia. It’s a family-friendly trail in terms of difficulty, and the views are breathtaking. A must-hike.

Watching the river flow by with a margarita in hand is one of the best ways to while away an afternoon in San Antonio, and at Casa Rio, you can do just that. The restaurant’s colorful umbrellas have lined the River Walk since 1946, providing a postcard-perfect backdrop for sampling enchiladas, flautas, fajitas, and, of course, icy-cold margaritas. The oldest restaurant on the riverfront, Casa Rio is beloved for its authentic Tex-Mex cuisine, but its real charm lies in its ambience. Request an outdoor table and let your worries float away with the river. Just be sure to decide between frozen and on the rocks first.

A piragua is shaved ice with syrup. Piragueros (the piragua vendors) and their colorful wooden pushcarts used to be ubiquitous in Puerto Rico many years ago. Now they’re few and far between (usually found in town squares) and with the heat bearing down more than ever, locals run to every piraguero they can find for equal parts refreshment and reminiscence. The most loved syrup flavors include raspberry, sesame seed, anise, and mantecado (ice cream).

La Gintonería, in the less-traversed neighborhood of Gros, could very well be the best gin-tonic in San Sebastián. With two shelves laden with premium and hard-to-find gins, it’s a gintonaholic’s dream. They have a selection of premium tonics and an arsenal of techniques to match. Watch as they instantaneously infuse your gin with cardamom using a pellet of dry ice. Or inhale as they drip just a few drops of bitters into your fishbowl glass. Whatever gin you choose, you are in for one of the best mixed drinks of your life.

The fragrant, pleasingly cluttered Central Grocery is a holdover from an era when Italian-run groceries occupied storefronts throughout the city. This timeworn shop across from the French Market still boasts an old-world charm, filled with tall shelves crowded with imported goods and various whatnots, mostly Italian. But that’s not why you’ll see lines out the doors. The crowds are clamoring for muffulettas, classic New Orleans sandwiches that originated here about a century ago. (Slogan: “Imitated by many, but never duplicated.”) A muffuletta comes on a type of round, flattish loaf (not unlike a focaccia) that originated in Sicily. The details may vary, but it typically includes cured meats (capicola, salami) and cheese (provolone). What distinguishes it from a hubcap-shaped hoagie is the topping—a tangy marinated-olive salad. Know this: You don’t need to order a whole one; a quarter-sandwich is still plenty filling for one person.

Just to the southwest of Tucson, on the San Xavier Reservation, sits the late XVIII-century Mission San Xavier del Bac, one of the finest examples of Spanish colonial architecture in the U.S. The combination of late Baroque and Moorish-inspired design is a beacon any time of the year, but on this winter day, the flooded fields worked some magic—panoramas of reflected landscapes are almost nonexistent in southern Arizona! The ‘white dove of the desert’ is the oldest intact European structure in Arizona, and it still serves as a parish church for the Tohono O’odham people.

JK Place Firenze is a far cry from Florence’s obsession with all things Renaissance. Set amid the buzz of Piazza di Santa Maria Novella, this onetime private mansion is decked out in black, white, peach, gray, and chrome, with inflections of 1950s movie stars, 1970s pop art, and ornate 19th-century architecture. The reception feels like a library, and the breakfast room is a glassed-over former courtyard with a hefty antique wooden communal table. Free drinks, fresh fruit, and homemade treats (and bubbles at cocktail hour) can be found at all hours in the guests-only lounge area. Impress your well-heeled friends by inviting them to dine on the piazza terrace, presided over by the appropriately black-and-white Basilica di Santa Maria Novella, before moving downstairs to the clubby J.K. Pink Room. Slip upstairs to your individually designed room for a divine night’s sleep, then awake ready to take on one of the world’s most historic cities.

Dario Cecchini is the most famous butcher in Italy and is probably the only one who recites Dante while carving up his carcasses. His small shop on the outskirts of the medieval village of Panzano is a Mecca for carnivores seeking quality meat (plus curious tourists), and he also has a restaurant—Solociccia—where you can sample some of the best bistecca in the region. If you visit his Antica Maccelleria Cecchini on a Sunday morning, when he works to a background track of jazz and opera, you’ll be offered a glass of wine, a hunk of pecorino cheese, and a nibble of some of his meaty products (like the fennel-flavoured salami called ‘finocchiona’) to ease the waiting time.

Centuries-old catacombs decorated with human bones pepper the crypts at this Franciscan monastery dating to 1774. Decked out in impressive Spanish Baroque architecture, the canary-yellow church and monastery also house a remarkable library with some 25,000 antique texts (some predating the Spanish Conquest) and are flush with romantic courtyards and cloisters. Don’t forget to look up: A magnificent Moorish-style cupola, carved of Nicaraguan cedar in 1625, oversees the main staircase.

This isn’t your average shopping mall. Forget about fast-food courts and trinket shops. Phipps Plaza is home to more than 100 stores, including those with names like Tiffany, Saks Fifth Avenue and Versace. Phipps also has an AMC movie theater, Legoland Discovery Center, and a handful of restaurants including Davio’s Northern Italian Steakhouse, The Tavern at Phipps, and Twist.

In Tucson, gelato is, understandably, becoming part of the cityscape. A handful of Italian gelato-masters have settled here, educating desert palates with tempting desserts. Here, just a few blocks from the University of Arizona, Allegro rotates its offerings in style—literally. (I mean, come on, isn’t this the coolest frozen dessert display?) Flavors such as saffron and anise, or even avocado, beckon on a hot evening.