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Why we love it: A historic building turned stylish hotel with a buzzy restaurant and lavish spa

The Highlights:
- Chic decor that mixes historic preservation with contemporary style
- A rooftop cocktail bar with citrus-inspired drinks
- Amenities like an on-site boutique, open-air yoga, and house car service

The Review:
Much has been written about Charleston’s antebellum charms, but modernists seeking respite need look no further than The Dewberry, a 1960s federal building on Marion Square that’s now one of the city’s coolest hotels. Here, a wood-paneled lobby gives way to a cozy living room straight out of Mad Men, complete with mid-century furnishings, antiqued mirrors, live music, and a brass bar serving up deviled eggs and classic cocktails. Up a flight of stairs, the second-floor spa features tufted-velvet recliners and treatments that incorporate Lowcountry flora, plus a full-service fitness center and open-air yoga classes on the hotel rooftop.

The 155 light-filled guest rooms are equally stylish, with luxurious Irish linens, marble baths, and armoires clad in custom-printed linen by local illustrator Becca Barnet. Barnet’s work is also on display in the by-reservation-only Citrus Club, a rooftop lounge with craft cocktails and light bites overlooking the Holy City’s famed steeples. For a heartier meal, guests can head to on-site restaurant Henrietta’s, where traditional French brasserie fare meets local ingredients. Rounding things out are unique amenities like house car service in luxury Volvos, complimentary Papillionaire bicycles, and a boutique curated by Garden & Gun, with fashion, barware, jewelry, and more from Southern artisans and craftsmen.

No one stays at Old Faithful Inn for the amenities: With no Wi-Fi, air conditioning, or TVs in the rooms—some don’t even have private bathrooms—all you can do is watch bison graze unperturbed by the busloads of tourists pulling up, or the namesake geyser spout. The lack of luxury doesn’t seem to deter the crowds, though, who come to sleep under the roof of the original log-and-stone building, which was completed in 1904, and launched the iconic architectural style known as National Park Service rustic, or Parkitecture. Though an east wing was added in 1914, and a west wing in 1927, the lodge remains much as tourists saw it a century ago, with its soaring, open lobby surrounding an enormous four-sided, 86-foot stone fireplace. The pre-existing Crow’s Nest that leads to the roof terrace is off-limits now, but two mezzanine-level interior balconies are coveted seating areas for unwinding with nightly piano performances. While the two wings have better views of Old Faithful and the geyser basin, you can’t beat the Old House for its historic charm.

An undulating steel and glass canopy wows visitors who enter the Kogod Courtyard. Inside you’ll find diners from the museum’s café, tourists soaking their weary feet in the shallow fountain running across the space, and students taking advantage of free Wi-Fi in the light and airy setting. The modern roof seals the center of the old Patent Office Building, currently shared by the National Portrait Gallery and American Art Museum. Architect Norman Foster designed the roof to have minimal impact on the building by creating a support system that prevents direct contact and weight placement on it. Unlike most of the other Smithsonian Museums located on the Mall, this gem is found in the busy Penn Quarter of downtown D.C. It is my favorite place to bring visitors, not only for the impressive courtyard space, but also for the preserved architecture of the patent offices on the top floor. Check the Smithsonian’s website for special courtyard workshops, concerts, or events. The museum is right near the Gallery Place/Chinatown Metro on the green, yellow, and red lines.

There are now 35 locations of Eataly, the massive Italian food hall, around the world, with 18 of them in Italy itself. The New York City one at Fifth Avenue and 23rd Street, which opened in 2010, was the first in the United States (it’s been joined by others in Boston, Chicago, and Los Angeles, as well as by a second outpost in Manhattan, near the World Trade Center site at 101 Liberty Street). For connoisseurs of all things Italian, this is a must-visit—or, more accurately, a must-shop and must-eat stop. Covering more than 50,000 square feet, Eataly NYC Flatiron includes five different restaurants (plus occasional pop-ups) offering opportunities to graze on antipasti, fish, pizza, and other dishes. A popular rooftop beer hall is open all year round (thanks to space heaters and a retractable roof). While you will want to eat your gelato on the spot, there are also a number of stores where you can buy gifts from biscotti to olive oils to take home a little bit of Italy via New York.

With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.

Located at the end of the town pier in Fort William, on the historic Road to the Isles, Crannog Restaurant is purely of its place. Local fisherman Finlay Finlayson opened the restaurant after converting his bait shed—which served as a lookout point during World War II—into this beautiful, red-roofed building, choosing the name “Crannog” as a reference to his concept of catching, curing, and cooking the finest West Highland seafood. Over the past 26 years, the eatery has become synonymous with relaxed fine dining, drawing diners with a regularly changing menu of local catches like West Coast mussels, Loch Creran oysters, and hake, which comes crusted in herbs and topped with basil-walnut pesto.

Named for a Dominican-style fishing boat, this open-air restaurant and bar in Punta Cana’s elegant Marina Estates sits on a wooden deck built over the water. Whether you’re seated under the thatched palm roof or the open sky, you’ll have perfect views of the marina as you dine on fresh seafood like grouper ceviche and grilled Caribbean lobster. Also available are Mediterranean-inspired dishes such as caprese salad, spaghetti with pesto, and glazed lamb shank, as well as an extensive list of international wines.

On the ultra-exclusive island of Mustique, Basil’s Bar is a stargazer’s paradise—and not just at night. It’s a favorite of celebrities, meaning you never know just who will be seated at the next table. A series of roofs cover the open-air deck to shade diners from the hot sun and occasional shower as they enjoy tropical cocktails and freshly grilled lobster. Come for the dance party on Wednesday, the happy hour on Thursday, or the sunset jazz every Sunday at 5:30 p.m. Basil’s also hosts the Mustique Blues Festival at the end of January, with live music each night for two straight weeks.

Rue Saint Paul is the oldest, the most popular, and the most iconic of Old Montreal streets. It was Montreal’s main thoroughfare in the 18th and 19th centuries, and although it doesn’t hold the same strategic importance today, it’s still at the core of Montreal’s destinations. Despite the tourist shops filled with souvenirs like moose-shaped shot glasses and maple-syrup everything, Saint-Paul Street still holds the grandeur it had back in the day, thanks to its stunning architecture. Ignore the shops and look up, admire the details of the windows and roof lines—to see what the street really is about. This street is ideal for a romantic, dimly lit, post-dinner stroll.

The state-of-the-art, 36,700-seat Marlins Park in the heart of Downtown is the home of the Miami Marlins baseball team. It has a retractable roof that takes just 13 minutes to go from fully closed to fully open, and there’s a floor-to-ceiling glass-walled concourse that overlooks glittery downtown Miami. The venue also houses a nightclub and several bars and restaurants—even one with a swimming pool. Take a group tour to see one of the country’s most high-tech baseball fields up close, including the field, the clubhouse, the batting cage area, the home run sculpture, the bobblehead museum—and the aquarium at home plate.

At this rooftop bar on the South Coast Highway, guests can pair breathtaking ocean views with well-made cocktails and delicious bites. There’s also nightly live music and plenty of high-def TVs throughout the space, making this the perfect place to party the night away or simply catch a game. Drinks range from craft beers and 22 wines by the glass to specialty cocktails like cucumber-jalapeño margaritas, while the food leans Southern, with options like gumbo, butter brisket, and jambalaya. Check the website before you go to see who’s playing that night; it could be anyone from a local DJ to a ’90s rock cover band.

Business travelers might help keep it quiet enough during the week, but when the weekend rolls around, the W Scottsdale earns its rep as a party hotel. By day, a young, trendy, and sometimes noisy crowd hangs at Wet, the rooftop pool, keeping well oiled with sunscreen and bar drinks. By night, the scene remains trendy, and noisy, at the lobby’s Living Room Lounge, or at Shade Lounge upstairs by the pool, often to a background of live music or a DJ, until the revelers are off to bed, or off to some of the many bars and clubs within walking distance. Rooms have all the tech gadgets, and the use of color and frosted glass makes them feel light and playful without going overboard.

Whether you have time to kill while waiting for your train or you simply like architecture, Milan’s main train station, Stazione Centrale, is worth a walk through for its epic 20th-century architecture. Originally designed at the turn of the century, Stazione Centrale has beautiful, monumental Liberty and Art Deco ornament in its main hall and entrances, while the platform area is covered in a gorgeous rooftop of iron arches. If you have a few more minutes, the Stazione also has some great shops, a traditional Motta caffe, and one of the best newsstands in the city.

This purpose-built luxury high-rise hotel has 400 rooms in all, with natural light spilling through floor-to-ceiling windows onto modern, clean-lined furnishings done in ivory and gray tones. Higher floors offer spectacular views of Lake Michigan and Navy Pier. Service here gets high marks for the nothing-is-impossible attitude of the staff, and from early summer to late fall the Streeterville Social, the third-floor roof top outdoor terrace, offers craft cocktails and relaxed dining… and views of the city skyline.

The second location of the Sydell Group’s New York flagship, NoMad Los Angeles embraces its past as the Bank of Italy—imposing columns and all. In the lobby of the landmarked building, much of the original Neoclassical style, such as the Doric columns, coffered ceiling, and marble floors, was preserved, complemented by the addition of floral textiles in rich jewel tones. Even the original vault, which once housed 12,000 safety deposit boxes, and its 50-ton door were kept intact. The color palette across the 241 lavish rooms draws from the exquisitely maintained gold-and-blue Italianate lobby ceiling, with custom furniture, original artwork from design studio be-poles, and freestanding bathtubs in most rooms adding to the luxurious feel. Details like nightly turndown service, marble bathrooms, and custom linens by Bellino mean a five-star stay is all but guaranteed.