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Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.

Original Joe’s has the same birth year as another pretty famous San Francisco landmark: the Golden Gate Bridge. Both are definitely worth checking out, but only Original Joe’s will serve you a hearty Italian meal in a red leather booth. Back in 1937, the restaurant was a 14-stool counter on Taylor Street where immigrant and family patriarch Tony Rodin served Croatian-Italian-American comfort food. Original Joe’s is run by the third generation of the family. A fire destroyed the first location in 2007, but the corner spot in North Beach that opened five years later can’t be beat. Inside, the family’s San Francisco history is revealed by walls hung with black-and-white photos, letters, and other ephemera. The menu showcases some of Tony’s recipes, such as eggplant parmigiana, Joe’s meatballs, and veal parmigiana. Those counter stools are there, too, saved from the fire and brought over to the new Original Joe’s.

Renowned Costa Rican architect Ronald Zürcher looked to his country’s colonial past when designing this hacienda-style property—witness its central courtyard, arched doorways, and terra-cotta roofs. Set amid a 30-acre coffee plantation just outside the capital city of San Jose, the hotel’s 308 traditional accommodations follow suit with dark wood furnishings, but a modern aesthetic pervades renovated guest rooms with streamlined furniture, intricately patterned bathroom tiles, and expansive views that extend from green lawns to forested mountains and urban skyline; some include small balconies that overlook the hotel’s two pools. On-site dining options include gourmet takes on Costa Rican fare at Hacienda Kitchen, Peruvian specialties at La Isabela, and fresh-made sushi at La Castilla, as well as a sports bar and café. The open-air great room invites reading and quiet conversations, but if you’re up for something a little more energetic, there are tennis courts, a driving range, a fitness center, and invigorating coffee scrubs at the spa.

Occupying three whitewashed colonial buildings sheltered from the bustling streets of Old Town Cartagena, Casa San Agustín sits on the site of a former aqueduct and channels its heritage with a swimming pool that tunnels through its stately remnants. Inside, common spaces feature a mix of Colombian art and artifacts with contemporary wicker furnishings and marble floors. The 20 rooms and 10 suites are cozy and a bit more polished than those found at other historic properties nearby: Units feature 200-year-old wood-beamed ceilings and iron canopy beds topped with Frette linens; some have patios with hot tubs or brick terraces with views of surrounding buildings. But there’s plenty of space to unwind throughout the property, namely a library with original frescoes and a lounge with a long wooden bar and ceiling-high wine cabinet. It’s a good idea to make reservations in advance for dinner at Alma, considered among the city’s best restaurants, where the upscale international cuisine includes fresh ceviche and dry-aged beef cured on-site.

Founded in 1971 as the first women-owned and operated community center in the country, the San Francisco Women’s Centers has been working to guarantee a safe space and reliable social services for women and girls in the city. And since 1979, they’ve done it from the Women’s Building—or El Edificio de Mujeres—in the Mission, a women-led community space advocating self-determination, gender equality and social justice. Through education, cultural arts activities, and economic services (all available in both English and Spanish), the Women’s Building helps more than 20,000 low-income women and their families every year. Looking to take part? Visit the website to see their list of events, rental spaces and equipment, and volunteer opportunities.

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.

Thanks to an owner and several staff members who hail from Italy, this Neapolitan-style pizzeria has an authentic feel that locals love. Its popularity shows—San Diego restaurants are rarely crowded, yet Buona Forchetta often boasts wait times of up to two hours. Much of the dining happens outside beneath an awning. Indoors, simple decor lets the gold Stefano Ferrara pizza oven shine. Go for perfectly blistered pies like the Nicola (mozzarella, mushroom, prosciutto di Parma, and truffle oil) or the Isabella (buffalo mozzarella, sun-dried tomatoes, onions, goat cheese, and rosemary). If Point Loma is more convenient, know that there’s a second, larger location called Officine Buona Forchetta in Liberty Station.

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.

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.

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.

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.

Most people who visit Florence know that walking to Piazzale Michelangelo is a must. However, fewer people know that walking a little higher to the old church of San Miniato al Monte is an even better experience. Amble down the Arno River to Viale G. Poggi, up the green pathways to Piazzale Michelangelo, then continue on until you reach the busy square with a bronze cast of Michelangelo’s David at its center. This church facing the square is one of the oldest in the area, a beautiful 12th-century example of Romanesque architecture. Note, especially, the mosaics on the facade and, inside, above the altar; the floor decorations are also worth a look. There is also a small shop next to the church, run by monks. Take in the views from the outside, stroll the grounds, and see the old cemetery. Entrance to the church is free, and if you’re lucky, you might even hear the monks singing.

With killer views of the waves crashing onto Ocean Beach, the Beach Chalet Brewery & Restaurant is one of the best places to grab a bite and watch the sunset in San Francisco. Before its current incarnation, the 1925 Spanish revival building served as a beach changing room, an Army outpost during WWII, and a VFW hall. The disused building was shuttered in 1970, but spared for its landmark WPA murals and mosaics. Come to see the murals, and stay for the food and Ocean Beach views. Upstairs, above the visitor center, the Beach Chalet Restaurant serves fresh fish and steaks. Downstairs, opening out to Golden Gate Park, the sunny and more casual Park Chalet offers burgers or fish and chips, and live music on weekends.