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In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”

The roots of this Mediterranean Revival-style boutique hotel go back to 1914, when a local grocer created the tropically inspired property to house his visiting vendors. Nearly a century later in 2010, hotelier and style guru Liz Lambert added the place to her mini-empire, reviving the grounds that still feature magnolia, palm, and cypress trees planted by the original owner. Set on a quiet section of the River Walk near the museum corridor, the restored building (which is on the National Register of Historic Places) houses 27 guest rooms decorated in a designer-meets-flea market aesthetic, with bright pops of color and plenty of personality. All are pet-friendly, and feature stocked SMEG fridges, Red Flower bath amenities, custom serape bathrobes, and complimentary coffee and Wi-Fi; suites have sitting areas, terraces, or other perks. Room service comes from the in-house Ocho restaurant, but it’s better to head down and eat there in person to take in the cheery setting, river views, pan-Latin menus, and cocktails that highlight rum (as a nod to Havana) and tequila (an homage to San Antonio’s Mexican roots). A regular calendar of happy hours, musical performances, and cultural events round out life at this vibrant hotel.

Surrounded by 40 pristine sand- and grass-topped acres, endless water views, and the sound of crashing waves, Bekal Fort—the largest fort in Kerala—feels like it rose up from the sea. In fact, it was built some three centuries ago as a defense post, lingering evidence of which includes the old ammunition storage areas and the cannon windows lining the outer walls. Today, visitors can wander around the complex, climbing up the observation tower, strolling around parts of the original walls, venturing out to the waterside walkways, and picnicking on the main lawns. (Along with the history and scenic beauty, the filming of some hit movies here has made the fort even more popular with domestic tourists.) After exploring the site, head down to the beach for some sea air and views of the fort from a different vantage point.

Founded in 2004, Cerveza Minerva is one of Mexico’s original—and biggest—independent craft breweries. Sample the spot’s regular brews along with a variety of special editions in its tasting room, where a glass wall offers views into the factory where the beer is produced. There’s also a full food menu to complement what’s on tap.

Expect to be transported back to medieval times during your visit to Château de Chillon. More than 1,000 years old, the beguiling castle has inspired many poetic greats, none more so than Lord Byron, whose poem The Prisoner of Chillon was based on François Bonivard’s imprisonment. Travel across Lake Geneva on a paddle steam boat to arrive at the castle and note that the Rivera Pass, offered by most hotels, grants you half-price admission. Once inside, pick up an audio guide (available in English) and explore everything from cobblestone courtyards and eerie dungeons to secret passageways and castle walls.

With dark walls, natural wood accents, and red curtains in front of the elevators, the trend-setting Andaz hotel feels like more of a scene than any other property in downtown Napa. In the center of downtown Napa, the hotel is mere steps from restaurants, shops, and arguably Napa’s best pub: the Norman Rose Tavern.

On check-in, all guests over 21 receive a complimentary glass of red or white wine. The swanky vibe continues into the 141 guest rooms, where hardwood hickory floors complement white marble bathrooms and midcentury modern furniture. The most convivial space in the hotel is the Mercantile Terrace, a second-story roof deck with a full bar menu and fire pits, a favorite of couples and business travelers alike.

The lounge is operated by Mercantile Social, the restaurant in the lobby that serves small-plate food items and cocktails; it also books live acoustic music sets a few nights a week. (And Mercantile Social sponsors free wine tastings daily.) If you haven’t had enough wine, fear not—on site are two tasting rooms from the wine empire built by Napa native John Anthony Truchard: John Anthony and JaM Cellars.

When the hip Andaz hotel chain opened in downtown Napa in 2012 it brought a youthful energy to wine country. In addition to its affordable rooms and excellent locavore-minded small plates restaurant, Farmer’s Table, the Andaz also gives guests a dose of culture. The brand’s Andaz Salon program introduces art, photography, music, and readings throughout its different properties.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

The mysterious rooftop of Casa Mila both charms and haunts visitors. The glorious October sky above frames the organic forms, each sculpted face watching as I creep up and down the rolling ramps. Children can’t resist playing here, and fortunately there are now fences all around. In my mind, I erase all of those pesky safety features to envision the smooth sculptures growing towards the sky from a scrolling sandy field. Once a site for a scene from Star Wars, the rooftop is now a destination for lovers of Barcelona and Antoni Guadi’s “Modernisma” style. When you visit, you’ll learn the secret behind those long vertical faces rising up above the mystical rooftop.

Mexico City is full of architectural masterpieces, but there is nothing like the experience of being inside a Barragán-designed home. Very few are still in good shape and open to the public, including Casa Luis Barragán (the architect’s former home and studio that’s the only private residency to be named a UNESCO World Heritage site). Once you’ve visited this more famous house, get in touch with the owners of Casa Gilardi and ask for a tour. The last project Barragán completed before he died, Casa Gilardi is known for the huge jacaranda tree decorating its interior courtyard, and for a striking hallway with vertical apertures that bounce sunlight against brightly painted yellow walls and out into an electric blue room with an indoor pool. The artist James Turrell spent a month living in the house, taking black and white photos to study Barragán’s use of light.

One thing you’ll likely notice when walking the streets of Cuzco is how many places advertise pizza. If you’re dying for a slice, there’s no better spot than La Cantina. Primarily a wine bar—bottles of all-Italian vintages line the walls—this place also happens to serve the best pizza in town, with a delicately thin crust topped with ingredients like authentic salami, prosciutto, arugula, olives, a variety of cheeses, and more. You’ll also find imported meat and cheese plates, lasagna, bruschetta, and salads. If you’re lucky, there’s tiramisu at the meal’s end, plus artisanal limoncello. Go for the wine, but be sure to try the food while you’re there.

Hop on a lightweight bicycle and learn about the history of the Philippines on a guided bike tour around Manila’s old walled city of Intramuros. The bikes are handmade in the Philippines from bamboo, a natural vibration dampener, and fibers from the abaca plant (similar to a banana); Bambike Revolution Cycles won a Manila FAME Katha Award for Eco-Design in 2015. This is a unique alternative to a walking or bus tour, and takes you inside a walled city that is not normally accessible to bigger groups. Intramuros almost doesn’t feel like Manila: The Spanish influence is evident in the architecture, which includes some of the oldest baroque churches in the Philippines. Fort Santiago still houses underground dungeons as well as a tiny underground chapel, hidden at the end of a tunnel. At the Rizal Shrine you will learn about the life of José Rizal, the country’s national hero who played an instrumental role in the Philippine rebellion against Spanish colonial rule, and follow in the footsteps he made as he took his last walk in the fort from his cell to his execution.

Set in a refurbished Victorian hunting lodge on a 26,000-acre estate, Shieldaig Lodge is the epitome of Highland romance. With everything from breathtaking views of Shieldaig Bay to log fires, cozy lounges, and an extensive whisky and gin collection, the hotel offers Scottish hospitality at its finest, surrounded by stunning scenery. Quietly elegant, the 12 guest rooms come furnished with antiques and luxurious touches like Egyptian cotton sheets, goose-down duvets, and homemade shortbread from the hotel’s kitchen. For utter opulence, book the suite, which features a four-poster bed, separate sitting room, and rolltop tub with views of the bay.

At the restaurant, rare-breed lamb, Highland cattle, and deer from the hotel’s estate provide the raw ingredients for the sumptuous menu. Also available are crabs, lobster, langoustines, oysters, and scallops caught by hand right in front of the property, and vegetables grown in the on-site walled garden. After dinner, grab a nightcap in the Liberator Bar, which stocks an ever-growing collection of more than 110 gins and 250 whiskies from around the world. The next day, visit the lodge’s falconry (home to eagles, falcons, hawks, and owls), or have the concierge arrange a local activity, from deerstalking and fly-fishing to hiking, boating, and pony trekking.

San Miguel is known as a community of artists, but to fully appreciate that understatement, every traveler should get closer to the city’s arts community. This village is a place where many have reinvented themselves as the next Picasso or Basquiat. First stop? The art galleries at Fábrica la Aurora, where visitors browse, shopping to add to their collections, with choices from the genres of painting, drawing, and sculpture. Longtime local favorites include Peter Leventhal—whose Rubenesque nudes adorn many a wall across the globe—and his wife, multimedia artist Terra Mizwa; abstract artist Merry Calderoni; and Annie Evans, whose sculptures of devilish women are mesmerizing. Art galleries also abound in the Centro and nearby San Antonio district. Events calendars detail monthly art walks.

Stirling Castle is one of Scotland’s most impressive castles, particularly for its role in Scottish history—several kings and queens were crowned here, including Mary Queen of Scots. Tour the Great Hall, the lavish Royal Palace, the elegant Chapel Royal, and the Great Kitchens, then check out Argyll’s Lodging (Scotland’s finest 17th-century town house, built just beyond the castle walls for a great nobleman serving the royal court). Also worth exploring are the peaceful Queen Anne Gardens and the Stirling Heads Gallery, which features 16th-century oak medallions carved with images of royalty, Roman emperors, and characters from the Bible. When you’re done roaming the interiors, head outdoors and walk the ramparts to appreciate the castle’s commanding position above the Royal Burgh of Stirling.

Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, but the original clean lines and sharp angles of the midcentury modern architecture coupled with Kelly Wearstler’s playfully eclectic interiors are still unmistakable at this stunning property overlooking Meads and Barnes bays. Epitomizing tropical modern luxury, the property is awash in marble, natural stone, and wood, with dramatic views of the Caribbean Sea from dining rooms and infinity pools that seem to hover from their cliffside perches. Spanning 35 acres, the resort is home to 166 spacious, serene, and stylish accommodations ranging from suites to townhomes and private villas. Indulge at five dining venues, including the aptly named alfresco Sunset Lounge for sushi and the fine-dining Cobà, where fresh seafood is paired with choice cuts of meat and an impressive wine list. With three swimming pools and two distinct beaches to choose from, the most stressful part of the day is deciding where to lounge.