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There was some trepidation among locals when Rosewood first announced its plans for this 13 plus–acre resort—the largest in the UNESCO World Heritage Site’s cobblestone historic center. But it didn’t take long for both residents and repeat guests to embrace it. The property evokes an authentic sense of place, with buildings made with the limestone used to build parts of the old town, decor crafted by local artists and artisans, and the same beloved ladies making fresh tortillas and sopes at breakfast since the hotel was under construction. Designed to feel like a hacienda, the 67 rooms and seven multibedroom townhouse residences—some of which are available to rent—are scattered around intimate courtyards and gardens, many featuring art and sculptures; a large outdoor pool, rotating indoor art gallery, and spa featuring treatments inspired by indigenous healing traditions are also on-site, while programs such as the Art Concierge help engage guests with the destination. The cuisine is also a big draw: Savor reimagined Mexican flavors and learn about regional wine at the gourmet restaurant; try a tequila tasting at the bar, which turns into a sushi-and-craft-beer spot on the weekends, or join locals for the popular Sunday brunch.

Hailed as one of the country’s first true boutique hotels, Hotel San José started its life as a 1930s tourist court and became a 1950s roadside motel before falling into disrepair in a bad part of town. In the mid-1990s, Liz Lambert bought it and transformed it into a minimalist, mid-century–inspired hot spot, the first of her distinctive Bunkhouse hotels, and the South Congress neighborhood changed with it. Although it’s now a must-visit for out-of-town hipsters (and its bar a hangout for trendy locals), the hotel stays true to its roots; a majority of the furniture was made by local artisans from reclaimed wood and Texas leather, the three most affordable rooms have a shared bath, and Lambert’s experience renovating the hotel and contributing to the neighborhood’s gentrification prompted her to make the documentary The Last Days of the San Jose.

Nowadays, SoCo is Austin’s hottest neighborhood, and Hotel San José is in the heart of the action, hosting local and touring bands in its courtyard and parking lot, and offering some of the city’s best coffee at Jo’s, its affiliated café. Plan to spend at least one evening making new friends over Shiner Bocks at the long tables in the courtyard lounge.

The Victorian-era glass and wood structure, which looks like a sugar-coated castle atop a grassy slope, is Golden Gate Park’s oldest building. It’s also one of San Francisco’s most splendid historic sites. Wander through five different galleries housing 1,700 species of aquatic and tropical plants along with the world’s largest public collection of high-altitude orchids. The potted plant gallery features rare flowering plants and an assortment of decorative urns and containers from all over the world, including a leftover from San Francisco’s 1915 Panama-Pacific International Exposition. Keep your eyes open for special exhibits, including the annual Butterflies and Blooms, which transforms the conservatory into a magical garden aflutter with hundreds of butterflies.

What could make a spa with all the typical trappings of luxury even better? Wall-to-wall windows overlooking La Concha bay, that’s what. La Perla does not disappoint, and it’s a great way to spend those finicky winter days when visiting San Sebastián. They also offer massages, which I highly recommend.

Be Bop is a staple in the San Sebastián night scene. If you are with a diverse group and uncertain how to reconcile their tastes, take them to Be Bop. Be Bop plays a wide range of music, from Michael Jackson to The Band to Bruno Mars. Drinks are cheap and the crowd is eclectic. It’s great for the hours before the discos begin to be crowded.

Shop for an authentic souvenir in Everything but Match, a store inspired by a T-shirt line designed by the owners’ 6-year-old daughter. In this shop in Old San Juan, you’ll find original art, accessories, and children’s clothing made by local artists and artisans. From unique jewelry to brightly colored throw pillows, you’re sure to fall in love with something unique to bring home in your suitcase.

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.

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.