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Hyde Park is happening. Catering to the University of Chicago crowd and its visiting dignitaries, the five-year-old Sophy takes inspiration from hometown literary and musical heroes, whose artworks ornament the walls in the popular and always convivial Mesler restaurant. Taking the title of the first boutique hotel on Chicago’s South Side when it opened in 2018, the property occupies a prime spot on 53rd Street—a vibrant commercial hub lined with shops and restaurants owned and frequented by a diverse population that range from academics to local politicians to the city’s cultural influencers. Former UofC professor Barack Obama’s home (and his under-construction presidential library) are nearby.

Lahaina, with its many Victorian flourishes, may look picturesque today, but the port town teemed with sailors, gamblers, and prostitutes in the 19th century. The Pioneer Inn changed all that when it opened for business in 1901, foreshadowing the tourist industry that would ultimately replace whaling, sugar, and pineapples. Step through the swinging doors of this vintage bar, which now bizarrely anchors the courtyard of a Best Western, and you’ll be transported back in time. Oars, harpoons, and a ship’s figurehead still adorn the space, looking down on platters of coconut shrimp, Parmesan-crusted fish over coconut rice, and margaritas made with POG (a mix of passion fruit, orange, and guava juices). Come during happy hour, which runs daily from 3 p.m. to 6 p.m., for discounted beers and cocktails.

Upon first glance, Circa Las Vegas revolves around sports betting: There’s a three-story sports book in the on-site casino and the pool deck features giant TV screens on one side and tiered, stadium-style pools and lounge chairs on the other. But the first new casino Downtown in more than 50 years also celebrates Vegas history: The design harkens back to Old Vegas dramatics, with art deco lighting in the high-limit areas of the casino and images of old-school gamblers inside the elevators. Owner Derek Stevens has even given a new permanent home to Vegas Vickie, a two-story neon kicking cowgirl who once graced the nearby stretch of Fremont Street known as “Glitter Gulch.” Vickie presides over an open foyer, seemingly nodding at guests as they wander around the casino.

Guest rooms at Circa—512 in all—have dark wood accents and carpets with geometric art deco motifs. Rooms in the Flex King category are equipped with king-size beds and couches that disappear when a second Murphy-style bed is pulled down from the wall. (Travelers who value selfies swear by the floor-length mirrors flanked by Green Room–style lighting.) Floor-to-ceiling windows offer epic views of either Stadium Swim or the Fremont Street Experience, a covered pedestrian walkway that forms the cultural and entertainment center of Downtown and was the main drag in the Vegas of yesteryear until the destination expanded with mega resorts to the south. The hotel also is a short walk from the unmissable Mob Museum, which offers a peek into the history of organized crime and runs a moodily lit speakeasy bar in the basement.

Related: 7 Hotels to Book for “Non-Vegas” People

Wobbly floors, a crooked staircase, dusty books, an old piano, and a few hundred years of character mix together in the beating heart of old Dublin, the Temple Bar. I spend more than half of every year on the road, calling in at one hotel and the next, and I’ve been lucky to have spent time at some fabulous hotels and holiday homes. This joint at No. 25 Eustace St. is near the top of the list. From the Irish Landmark Trust website: “The Irish Landmark Trust saves heritage buildings throughout the island of Ireland that are at risk of being lost through neglect or inappropriate use; conserving and restoring these buildings so they can be let as holiday homes.” The next time you’re in Dublin with your family or a large group, forget about calling in on modern digs, and check out No. 25, or one of the other heritage properties managed by the trust. It was a beautiful experience, and I can’t wait to check in again. Next time I plan to visit an old lighthouse, fort, or country home.

With majestic views of the Alps and a medieval old town, Innsbruck is not short on charm. Get lost among the colorful Baroque buildings of Herzog-Friedrich-Strasse, see the famous Golden Roof, view Lucas Cranach the Elder’s “Madonna and Child” at the St. Jakob cathedral, and enjoy the splendid rococo style at the Hofburg.

My favorite way to start a day in Tianzifang is with a hearty breakfast at Kommune. With a notably large courtyard, it’s a fabulous place to kick off a warm-weathered day and even if you’re a little chilly, the coffee comes in bowl sized mugs that will warm you right up. Open from 7am-1am daily. (They also have a great wraps at lunch and a happy hour from 5pm-7pm.)

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.

Situated at the top of the hill on Park City‘s iconic Main Street, the Italian restaurant Grappa occupies a beautiful 100-plus-year-old renovated building that over the years has been a brothel, bar, and bed-and-breakfast. The name comes from the Italian brandy distilled from the leftover grape skins, stems, and seeds from the winemaking process. And, of course, Grappa serves it! Founder and owner Bill White blends French culinary influences with regional Italian dishes to bring bold and delicious flavors to his customers. When the weather is appropriate, there are five levels of patios, complete with plants and water features for alfresco dining.

Honolulu’s last great tiki bar is tucked behind a row of warehouses, six miles northwest of Waikiki. Set on the edge of Keehi Lagoon, it shelters under plumeria and coconut trees—and will be familiar to fans of Hawaii Five-0. La Mariana defies the kitsch label: All those shell chandeliers, puffer-fish lights, and fishing floats suspended in nets are the real deal, with most items dating back to 1957. Carved tikis abound, alongside high-gloss tables fashioned from koa, the rich-hued wood from endemic acacias and the source of weapons and voyaging canoes for ancient Hawaiians. Go for the ambience and strong mai tais; the menu is straight-up, old-school surf and turf, perfectly tasty but uninspiring.

Often described as the Grand Canyon of the Pacific, this 10-mile-long Kauai valley is a kaleidoscopic array of scarlet earth, verdant valleys, and raw volcanic crags. Bands of color streak the corrugated landscape, each representing a different eruption and layer of lava. Waimea Canyon Drive has a series of lookouts; among the most popular is Waimea Canyon (past the Mile 10 marker on Highway 550), where a number of rivers once cascaded down the gently sloping shield volcano. When part of its flank collapsed, the rivers combined with dramatic results. Continue into the mountains to explore Koke’e State Park beyond. Its small, free museum contains a 3-D map, which sheds light on the canyon’s wild beauty, while the gift shop specializes in local art, crafts, and Niihau shell jewelry.

An easy, 10-minute trail leads to these paired cascades on the west side of the mammoth Morne Trois Pitons National Park—the higher, lefthand fall is known as Father (279 feet) and the smaller as Mother (131 feet). While the path stops at the viewing platform, visitors often descend and bathe in the pools, moving cautiously over the slippery rocks.

In an all-white open-air dining room that spills out onto the sand overlooking Meads Bay on Anguilla’s west end, Jacala serves just 35 guests a night. Chef Alain Laurent’s French-inspired menu includes dishes such as fennel-spiked conch chowder, snapper meunière, and a steak tartare prepared tableside upon request.

Colombian fashion designer Silvia Tcherassi took the design world by storm when she transformed a 250-year-old mansion in the center of Old Town Cartagena into a contemporary refuge that honors both past and present. Mansion Tcherassi’s seven rooms blend fashion-forward decor (think sparkly gold throw blankets) and original features such as restored stone walls and private balconies, but the vibe is much more understated, with ethereal fabrics, soft colors, and natural wood, in the 42 neutral-hued rooms at sister property Tcherassi Hotel & Spa. You can order fresh-caught seafood and icy raspaos (traditional drinks made with fruit and condensed milk) at the restaurant, while carpaccios, pizzas, and ceviches are on the menu on the rooftop lounge; the Italian restaurant at the mansion extends to a cozy patio facing a plunge pool and vertical garden made with thousands of local plants. After a day spent exploring Old Town’s historic buildings, relax with a Chinese medicine–inspired treatment in the spa, or take a dip in one of the property’s four pools.

Anywhere breakfast is served all day usually scores in my book. At Caficultura in Old San Juan, the food is “farm to table” and is as delicious as the creative menu sounds. In addition to the mostly healthy options, the highlight is the maple syrup made with rum, and coconut milk–dipped french toast topped with coconut shavings. The atmosphere was pretty cool—large black chandeliers hang from large wooden beams, and the picture windows face Plaza Colón outside.


Definitely a cool local place to stop into and grab a coffee or brunch while sightseeing throughout Old San Juan’s historic district.

What’s old is new again in Saint-Pierre, a city built under majestic Mount Pelée on Martinique’s Caribbean coast. In 1902, Mount Pelée volcano erupted, leveling the city and killing all 30,000 inhabitants– save one lucky prison inmate, whose thick cell walls protected him from the blast. Today, the rebuilt Saint-Pierre honors its fiery past at the Musée Volcanologique, a mini-Pompeii filled with carefully preserved relics. History meets modernity at the southern entrance where seven inspired, contemporary Caribbean artists have created 32 colorful totem sculptures welcoming guests. There are also popular dive sites nearby, where scuba divers can swim alongside century-old wrecks of ships that sunk in the explosion.