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A year ago I had dinner at the Clifton, then under the supervision of Tucker Yoder. Mr. Yoder was elsewhere that evening, but I spent several hours at the “chef’s counter” in the kitchen, watching executive sous-chef Jarad Adams work his own delicious magic. Naturally Mr. Adams was meticulous with his food prep, but he was also surprisingly generous with his time for me. Imagine my delight when I returned this year to find Mr. Adams had been promoted to Executive Chef. On this visit, Mr. Adams’s tasting menu showed the same attention to detail as I remembered, but with a greater sense of adventure — even whimsy. From the amuse bouche (a spoonful of polenta topped with pork belly, apple, and a sprig of fennel) all the way through to the sticky toffee pudding with candied pecans, dates, and caramel ice cream for dessert, I was enchanted. The tasting menu consists of four courses and varies by the season. My first course was a toss-up between the butternut squash and apple soup and the shaved winter vegetable salad with hazelnuts, black cocoa, and a buttermilk dressing. I had no regrets about my choice of the salad, especially as butternut squash was the foundation of my next course: the most perfectly seared sea scallop I can remember. From there it was onto monkfish with beluga lentils, with Brussels sprout leaves dancing on top. Mr. Adams knows what he’s doing in the kitchen, and the Clifton — and Charlottesville — is lucky to have him.

Touting itself as “killer burgers and manly drinks,” Urban Stack is an upscale bar food restaurant that just happens to be LEED certified. Choose from one of their signature burgers, with selections like standard beef burgers, alongside lamb, chicken, turkey and veggie patties. Urban Stack also prides themselves on their bar, which leans heavily on bourbon and, of course, “Tennessee whiskey.” Try the Dixie 8, made with Chattanooga Whiskey. The renovated Southern Railway Baggage Building is the best place to enjoy a cocktail in Chattanooga.

Beyond the crowds of central SoHo—in a formerly industrial nook with historic roots on the edge of the Hudson River—a neighborhood is emerging: Hudson Square. This is the home of Hotel Hugo, a stylish loft-inspired retreat with an Italian spirit that has brought a bit of European-inflected flair to the neighborhood. This extension of SoHo has long been known by New Yorkers for its nightclubs, restaurants frequented by locals, and of course, the gorgeous Hudson River Park, an uninterrupted promenade that stretches the length of Manhattan. Now it has a chic hotel, complete with a rooftop that has a Cuban cantina vibe that serves cocktails against a backdrop of the Hudson River.

In a peaceful pocket of the vibrant Chelsea neighborhood, the High Line Hotel is a charming boutique with many stories to tell. There is the tale of the grounds once being home to a 17^th-century apple orchard, or the history of the cloistered seminary inspired by the architecture of Oxford and Cambridge. This Federal Historic Landmark (where “‘Twas the Night Before Christmas” was written) softly transports guests to another era with its gas lamps, Gothic-inspired brick buildings, and original details including fireplaces. This property was thoughtfully created, from its historic preservation to the hand-selected furniture of antique fairs and vintage markets. With hardwood floors, whimsical prints, and tall windows overlooking the Parisian-inspired garden, these rooms feel more exclusive guesthouse than sleek hotel. Kick off your day with a latte from the Intelligentsia lobby bar.

Many New York hotels have style, but not all have character—the Marlton is a fine example of a property where the two are powerfully present. Originally built in 1900 as a cheap place to stay (and attracting the likes of writers including Jack Kerouac) this nine-story property was taken under the wing of hotelier Sean MacPherson (the Bowery Hotel, the Jane) and transformed into a downtown hot spot where no one seems to care that the rooms are tight on space, even according to New York standards. What square footage the rooms lack, the common spaces make up for—there’s a fire burning in the lovely lobby, complete with an espresso bar, along with a cocktail bar and French-feeling restaurant, Margaux, at the back, with a gorgeous, sunny solarium (a charming feature that has inspired many return guests). Rooms are thoughtfully designed, with inviting bathrooms. Striking the right balance between hip but not too fancy, the Marlton is a comfortable property that provides much more than just a place to sleep.

The creative energy of the Garment District in Midtown Manhattan has long been behind closed doors, but Archer Hotel, opened in early 2014, puts that artistic spirit on appealing display. A mix of fabrics, graphic prints, exposed brick, and floor-to-ceiling windows (with dramatic skyline views) pays homage to a neighborhood known for pushing the boundaries of fashion. Beyond its quirky style—including a house art collection with pieces spanning several mediums—this property entices with its rooftop bar, Spyglass, perched on the 22^nd floor with views of the Empire State Building and the Chrysler Building. Archer excels at the small stuff, from in-room Nespresso machines and free Wi-Fi to gorgeous black-and-white subway tiled bathrooms with luxurious walk-in showers. Unwind after your day with an aperitif at the Foyer Bar, complete with seasonal outdoor patio.

A buzz surrounds the Smyth, located smack in the heart of TriBeCa, with its recent reinvention: Chef Andrew Carmellini has revitalized the restaurant space, making it a destination for diners from across the city, and a redesign from Gachot Studios has brought a fresh feel to the decor. The new residential-feeling lobby is meant to be your TriBeCa living room, with all the neighborhood’s shopping, galleries, spas, Michelin-rated restaurants, and attractions right on the doorstep. One of downtown’s most poignant landmarks, the 9/11 Memorial, is a few short blocks away. Mirroring the neighborhood’s style, this hotel is understated and chic. Grab a stool next to TriBeCa’s designers, filmmakers, and photographers for a cocktail at the Evening Bar.

Atlanta is ripe with farmer’s markets and the Freedom Farmer’s Market, held weekly from March to December at the Carter Center, is one of the better ones. It has less stalls than others around town, but many of the vendors come from much further away to showcase their goods. Grab a warm pastry from the Star Provisions tent and a pour over coffee from 1000 Faces Coffee of Athens to sip as you wander the stalls. Bring your own bag to take home your haul of produce. Each week a local restaurant holds a pop up tent to showcase a unique dish only available there. You may even see former president Jimmy Carter walking around!

Want to sleep in Boston’s very first skyscraper? Originally constructed in 1893, the 15-story Ames Building was, for many years, the tallest building in the city. Renowned architect David Rockwell helped reconceive the building as the high-end Ames Hotel in 2009, preserving much of the original detailing. Many celebrities have since stayed in the luxury hotel, that’s now part of the Hilton Curio Collection, a collection of unique hotels steeped in history.

The rooms at the Ames feel more like opulent city apartments, with modernist furniture and eclectic details like feather chandeliers and gold-sequined pillows. The property’s historic roots are reflected in the 13-foot ceilings and Romanesque, floor-to-ceiling arched windows. Other classic elements include decorative marble fireplaces and oak wood floors. Centrally located in downtown Boston, the Ames provides easy foot access to many of the city’s best-known attractions.

Up-and-coming starlets in the 1920s and ‘30s would have stayed at the Crescent. When the palm tree–lined art deco building opened in 1927, it was as lodgings for the budding actresses who’d just signed studio contracts and moved out to L.A. for their big breaks. They, too, sipped cocktails (after Prohibition ended, of course) and listened to jazz (probably not by a live band, though) in the intimate lounge and on the breezy terrace. It’s even just possible there was saltwater taffy at the front desk and a library stocked with an impressive collection of classic and contemporary literature and nonfiction. However, the walls might not have been adorned with paintings and photographs by some of the area’s top artists, and there definitely wasn’t 24-hour room service or iPod docks.

After the studios moved on, and luxury designer shops and trendy restaurants moved in, the Crescent turned into a cozy, quirky boutique hotel known for its prime location, affordable rates, and bend-over-backward service. These things won’t change.

A breezy little beach hotel filled with rough wood, natural linen, and flea market finds, the Rose seems, to the uninitiated, like a pure product of quirky Venice’s hipsterfication. In fact, the historic, wood-and-stucco building was built by the beach town’s founder, Abbot Kinney, in the early days of the 20th century; rumor says it was his private brothel, frequented by such friends as Charlie Chaplin. By the 1970s, at the height of Venice’s drug culture, the building had become a flophouse of sorts, and neighbor Dennis Hopper was known to drop by. Before two British photographers discovered it, the house had turned into a mural-covered crash-pad for surfers, yogis, and beach bums of all kinds.

Looking at the low-key Rose now—the town’s first true boutique hotel, barely half a block from the beach—one would hardly know that the entire history of Venice had passed through it. The rooms are spare but stylish, with large windows, art photography, and vintage furniture. Some rooms are large enough to live in, whereas others share a hallway bathroom. Amenities are minimal—Stumptown coffee, bicycle rentals—but a relaxed beach house that attracts artists and creatives looking to delve into Venice’s eclectic, vibrant culture doesn’t need to try too hard to be cool.

As the first boutique hotel in Koreatown, the Line might have been able to get away with cutting a few corners while still attracting a cool clientele. It probably didn’t need to get the hottest young Korean-American chef in L.A. on board (to run one of the most comprehensive and exciting restaurant and bar networks yet seen, by the way), nor did the Sydell Group—the arbiters of cool behind the Nomad Hotel in New York—have to put their stamp on it. The hotel would have been nice enough had the concrete midcentury building not been entirely reimagined by designer Sean Knibb, known for designing half the cool spots in L.A. and more than a few celebrities’ homes. There didn’t need to be a desert greenhouse–inspired pool deck that’s become a hangout for beautiful people at all hours, nor did the famously trendy Houston Brothers (of no Vacancy and Harvard & Stone) have to throw in a midcentury-inspired cocktail bar. Nor did the typical hotel gift shop have to be reimagined as a design and lifestyle store curated by Poketo. The rooms and suites would have been just fine had they not been turned into artsy, industrial-style lofts, outfitted with original commissioned artwork, a minibar of Korean and Western snacks, and Baxter of California toiletries. Of course, all of this did happen, and now Koreatown is home to one of the hottest hotels in L.A.

Perched just up the hill from the white sands of Oneroa Beach on Waiheke Island, the Boatshed fulfills the wainscoted, shuttered, pitch-roofed holiday images that dwell in the minds of beach lovers the world over. Originally the vacation cottages of designer David Scott, the Boatshed now offers six sun-drenched accommodations that complement the laid-back island vibe—a magnet for a free-spirited set of artists, vintners, chefs, and water lovers. Many furnishings were custom-designed by the Scott family and exude the feeling of a boat cabin, especially when placed among the built-in shelves and cabinetry of the bachs—the local word for an authentic New Zealand beach shack. Accommodations range from old boat sheds to a three-story tower that feels like a lighthouse, and outdoor decks provide many opportunities to enjoy the sea breeze. The boutique hotel was the realization of Daniel Scott’s dream—to share the simple pleasures of the beach life with travelers from around the globe.

The first true boutique hotel on L.A.’s east side, the Hotel Covell fits into its trendy Los Feliz neighborhood so well that it feels like it should have been there for years. Created by a veteran of the Los Angeles bar and restaurant scene, the nine-room hotel takes its inspiration from a fictional character’s life: George Covell, an imaginary writer, started out in Oklahoma in the 1930s and ’40s before dividing his time between New York and Paris, where his daughter Isabel grew up. Each distinctively (and painstakingly) decorated suite is based on a place George or Isabel lived, from a rustic-chic Oklahoma house to a 1970s Parisian apartment.

Rising before one of the world’s most famous sailing sites—the host of the Louis Vuitton Regattas, the Volvo Round the World Race, and the Auckland International Boat Show—the Sofitel Auckland Viaduct Harbour blends French and South Pacific influences while respecting the maritime heritage of the area. Glass walls maximize views of the marina and its many yachts as well as the reflective pools that create optical illusions in the hotel lobby. The color palette sets cherry and dark woods, jade greens, and slate grays against cream and white backdrops, while artwork—from ceremonial pieces to a Maori tribal sculpture in the atrium—pays homage to indigenous New Zealanders. Some of the treatments at the SO Spa, like the greenstone massage, also reflect local culture, while others use French products in a nod to the hotel brand’s heritage.

References to Auckland’s volcanic origins also abound, most notably in the back-lit marble walls of the Lava Dining restaurant, an all-day spot for French- and New Zealand-accented dishes; the casual 21 Viaduct Café and panoramic Sabrage Bar are other dining options. And then there are the rooms: from the Superiors and Junior Suites to the exclusive Opera Suite, all have contemporary décor, signature MyBed mattresses, marble baths with Lanvin products and separate showers and tubs, and walls of windows opening out onto a Juliet balcony with views of either the hotel’s atrium, or the city, harbor, and beyond.