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Set at the end of Duval Street, near Sunset Pier and Mallory Square, Pier House takes advantage of its waterfront address with three tiers of balconies and a pocket-sized stretch of private beach. Its location means guests are within walking distance of all of Old Town’s highlights, from the Clinton Square Market to the Harry S. Truman Little White House. Many come to follow in the footsteps of the mayor of Margaritaville himself, Jimmy Buffet, who played his first gig in town in the hotel’s now infamous Chart Room Bar. Order a rum runner, then head to the heated outdoor pool; though it’s on the small side, it has sweet views to Key West Bight. After an adventure-packed day, the rooms and suites offer low-key comfort, decorated with traditional furniture and local art and overlooking the ocean or tropical gardens and koi ponds. Equally serene is the full-service spa, one of the few on Key West.

Bavaria meets Florida at this Marriott Autograph Collection property, midway between downtown Orlando and the theme parks, and close to the Orange County Convention Center. The hotel’s unique decor pairs antlers and fake fur with pastels and palm trees, and adds elaborate chandeliers and original artwork throughout. Accommodations have fairy tale–inspired carved headboards and marble bathrooms; book a corner room for a separate seating area—in a turret overlooking the lush grounds. The Poseidon spa pampers you like royalty with body, skin, and beauty treatments that employ ocean-derived ingredients, and massages can be arranged in room or in the garden. Breakfast and lunch are served at the bright and airy Garden Bistro, with dinner and drinks available in the Antlers Lounge, but you can walk to restaurants and attractions along International Drive, including the Orlando Eye Ferris wheel. Just be back before dark: From the Sky Terraces, guests have views of nightly fireworks and may spot another nearby castle—Hogwarts at Universal Studios.

The first hotel to arrive in Denver‘s up-and-coming River North Art District (RiNo), The Ramble brings even more style to the increasingly trendy neighborhood. Accommodations in the 50-room boutique hotel feel both design-forward and homey thanks to antique Persian rugs, a cool color palette, and rich textures. Personal iPads make room service orders easy, and the mini-bar is stocked with carefully chosen snacks (gluten-free vegan protein bars, organic peanut butter cups). As notable as the rooms themselves are, the drinking and dining offerings—all provided by acclaimed New York bar Death & Co—are the real story. For those many days of Denver sunshine, grab a seat in The Garden, an open courtyard space. An intimate 20-seat bar with a cocktail tasting menu overlooks the lobby restaurant, where dinners feature small bites as well as family-style fare. And at the event space Vauxhall, a dedicated bar will host events like film screenings—and, of course, Broncos game viewings.

The constantly evolving Seaport District just got even cooler with the opening of Mr. C Seaport, the first New York City hotel from Maggio and Ignazio Cipriani. An intimate 66 rooms make up the seven-floor property, each one showcasing a rain shower, 50-inch interactive 4K television, and fine Italian linens by Casa Rovea. Timeless luxury is the goal here, evident in the rich textures, classic color schemes, and thoughtful collection of handmade Italian furniture. Upon arrival, visitors are greeted with an on-the-house Bellini, a gesture that pays homage to the classic cocktail created by Giuseppe Cipriani in 1948. It’s also a nod to the hotel’s restaurant Bellini, which offers an array of rustic Italian dishes (think lasagna Bolognese and bucatini cacio e pepe). When guests feel like venturing beyond hotel limits, they have a couple of options for wheels: a fleet of 2018 Lincoln Navigators for rides within 15 blocks, and a custom collection of Mr. C Seaport bicycles by Fourth Floor Distribution.

This casual, open-air restaurant sits above an untouched stretch of Laguna Beach—and capitalizes on that beautifully. Floor-to-ceiling windows encircle the dining room so it appears to be floating above the ocean, all the better to watch the sunset while eating hand-shucked oysters and sipping Rum for Your Life cocktails. Chef Rainer Schwarz’s menu centers around seafood, prepared with a range of international influences—Spanish octopus is grilled with chickpea puree and zahtar, and lobster stars in a spaghetti carbonara. The spot draws a stylish crowd not just for dinner but also weekend brunch, with a must-try version of eggs Benedict (made with Berkshire ham and blood-orange hollandaise, plus steak or crab). While waiting for a table, sidle up to the Stateroom Bar, the former home library of Old Hollywood actor Slim Summerville, for artisan libations heavy on fine bourbon and whiskey. Pro tip: Locals know best, and they can’t get enough of the whole fried branzino, served with roasted shishitos and ponzu sauce.

Over the past few years, the Catskills region has been heating up with boutique lodgings that make it easy to soak in fresh mountain air in style. One such spot is Eastwind, a 1920s bunkhouse with 16 cozy, Scandinavian-inspired rooms (think reclaimed-wood flooring, Turkish rugs, Frette linens, and en-suite baths with farmhouse sinks and walk-in showers). For those who prefer to commune more closely with nature, the hotel also offers three minimalist, A-frame glamping cabins with private fire pits, as well as a hot tub and sauna for soothing steams after a day spent hiking Kaaterskill Falls or swishing down the slopes of nearby Windham Mountain. Each morning, guests can enjoy an impressive breakfast spread of pastries, eggs, make-your-own crêpes, and more in the bar-cum-living-room, equipped with a communal table, velvet armchairs, and a wood-burning fireplace. Come evening, they can return to the same space for expertly made cocktails and games like chess and backgammon.

For a New York experience that’s equally extravagant and convenient, visitors should consider a stay at this five-star hotel, located just blocks away from Midtown Manhattan sites like Central Park, the Museum of Modern Art, and Carnegie Hall. Built in 1904 by John Jacob Astor, the Beaux-Arts building houses 239 rooms across 20 floors, plus an incredibly prized means of accessing each one—an original brass-and-marble staircase runs from the lobby level to the 19th floor (a development that cost Astor $1 million of his $5.5 million investment in the hotel). Once guests do land in their rooms, it will be tough to leave thanks to the signature butler service, available 24/7 for any number of requests, from the everyday to the once-in-a-lifetime. One of your asks should most definitely be a reservation at the on-site King Cole Bar, where bartender Fernand Petiot allegedly invented the Bloody Mary in 1934.

When it opened in 1969, the Fairmont Dallas set the bar high for luxury hotels, dazzling visitors with opulent interiors, a Neiman Marcus outpost in the lobby, and 11 separate kitchens. Its legendary Venetian Room hosted acts like Ella Fitzgerald, Jerry Lewis, and Ike & Tina Turner. Now an integral part of the downtown skyline, the hotel remains a favorite for a whole new generation. The 545 rooms are bright and sophisticated, with city views, marble bathrooms, and minibars stocked with organic options. In a nod to its Arts District location, the hotel hosts a unique local artist-in-residence program, and the Four Diamond–rated Pyramid Restaurant and Bar pulls ingredients from a 3,000-square-foot rooftop vegetable and herb garden for its “terrace-to-table” modern American fare. There’s no spa, but wellness is represented with a 24-hour gym and a Junior Olympic–size pool, where guests can also enjoy family-friendly “dive-in movies” and evening DJ sets in the summer.

In December 2017, one of the country’s oldest Ritz-Carlton properties was rebranded as The Whitley, and though the name may have changed, the property’s high standard of elegance endures. The 507 stately guest rooms—which start at a spacious 720 square feet—are currently undergoing a refresh (but still include comforts like high-thread-count sheets and Nespresso machines), and the restaurant and bar have been reimagined as Trade Root, a Mediterranean-meets-Southern lounge featuring house-made pastas, an extensive selection of cheese and charcuterie, and craft sodas and cocktails. Guests can avail themselves of the indoor lap pool—a top-floor beauty with a stunner of a glass roof—as well as a fitness center and spa, or indulge in a little retail therapy in the neighboring shops of Buckhead. No doubt further renovations will ensure that this hotel remains an icon well into the next generation.

The Blue Ridge Mountains stand in for the Black Forest at Grand Bohemian Asheville, a 104-room luxury property inspired by old-world Bavarian hunting lodges, complete with stag-antler chandeliers, rich velvet and brocade textiles, and a popular mascot in the lobby—a taxidermied wild boar named Zsa Zsa. In contrast to the more dramatic public spaces, rooms and suites are spacious and light with crisp white bedding and tufted headboards; almost all of the bathrooms have large tubs with shutters that open up to the sleeping area. In addition to the rare original artwork that’s scattered throughout the hotel, there’s a gallery featuring paintings, art glass, woodwork, and sculptures from local, regional, and international artists. George W. Vanderbilt’s Gilded Age castle is across the street, and the hotel is within walking distance of Biltmore Village’s popular restaurants and shops and only two miles from trendy downtown Asheville, making it a convenient jump-off for exploring the Great Smokies.

Good, old-fashioned pie can be hard to find these days, which makes Betty’s in Encinitas more than worth a trip. Don’t be turned off by the location in a strip mall, Betty’s pies are delicious; they always use real fruit, pure butter, premium chocolate and local eggs. Betty’s doesn’t sell pie slices, hence the name Betty’s Pie Hole, but they do make sweet and savory pies in individual and full-size portions. The chicken potpie is hearty and delicious—but it’s the fruit pies, like the perfectly balanced strawberry-rhubarb with a flaky crust, that you’ll be dreaming of for days.

If you’d like the space and privacy of a vacation apartment but still want the service and amenities of a hotel, the Cottages & Lofts at the Nantucket Boat Basin are ideal. You’ll be whisked away from the Hy-Line ferry and taken to the wharves of Nantucket’s harbor, about as close you can get to the water without staying on a boat. Cottages and loft rooms range from studio-size to three bedrooms, all with full kitchens and private patios. A complimentary shuttle bus can take you to the beach, and bicycles can take you wherever you can’t walk from the cottages. There’s no restaurant on-site, but plenty of options are at the marina, and guests get a discount at the White Elephant’s Brant Point Grill. Children and pets are VIP guests as well: Kids get fishing and beach gear to use during their Nantucket stay, and a pet concierge will assist with stays at the “Woof Cottages.”

Outdoor and culinary adventurers alike are drawn to this 11-acre property situated at the entrance of a stunning seven-mile fjord in Kachemak Bay. Guests can kayak through hidden coves to glimpse otters and porpoises, hike past alpine meadows, or deep-sea fish for salmon. But where Tutka Bay really separates itself from other Alaskan lodgings is in its culinary offerings. Visitors dig for steamer clams or stop by a local oyster farm for their evening’s feast, and continue the hands-on approach with lessons in the resort’s one-of-a-kind cooking school, housed in a repurposed crabbing boat. The focus ranges from Kachemak Bay cuisine to global influences, prepared with regional seafood and homegrown vegetables. After dinner, you’ll retire to one of six comfortably furnished oceanfront cabins, the most exclusive of which has three bedrooms and is surrounded by old-growth Sitka spruce trees.

The Darcy is high on style and also loaded with substance, thanks its eye-popping design, contemporary art collection, and free amenities that make every guest feel like a VIP. Kids can check out a Darcy Daypack full of items chosen to encourage a space or art-themed adventure in the city. Gentlemen can take advantage of the in-house haberdashery service to borrow or buy a pair of cufflinks or accessory, or have a whole suit custom-tailored in their room. A bike and scooter rental helps guests explore beyond the trendy Logan Circle neighborhood, while a nightly happy hour gives a taste of local grain-to-glass Green Hat gin. The swank captain’s quarters of Siren Restaurant serves a seasonal seafood menu, raw bar and caviar service, and craft cocktails, while the Lil’B Coffee Bar goes full Southern with a day menu of espresso drinks and New Orleans favorites.

Hyperlocalism has fueled Portland’s Old Port District revitalization, with buzzy restaurants and shops with a deep sense of place opening in recent years. The stylish Press Hotel is no exception. A publishing motif runs throughout the 110-room property, which occupies a corner building that once housed the Portland Press Herald. Custom-made wallpaper printed with old headlines adorns the corridors, and desks inspired by those found in 1920s newsrooms are in each room. Works by local artists—including a dramatic installation of vintage typewriters from the late 19th and early 20th centuries by Portland artist Erin Hutton—and woven-wall tapestries by Portland home-goods designer Angela Adams also abound. (There are even a few notable—and welcome—nods to the global luxury market, including Frette linens from Italy atop the plush beds.) The focus at the 65-seat hotel restaurant, Union, is proudly farm- and sea-to-table, with dishes like house-smoked local mussels served with celery cream.