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  • Main St, Roosevelt Island, NY 10044, USA
    For panoramic views of the entire city—for the price of a subway ride—take the Roosevelt Island Tram. As the suspended car runs parallel to the bridge, spanning the gap between Manhattan and Roosevelt Island, you’ll have unparalleled vistas of the New York syline and the East River below. There are few experiences as memorable or accessible, so be sure to ride the tram there and back—it’s particularly dramatic in the morning and evening.
  • 1015 Navarro St, San Antonio, TX 78205, USA
    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.
  • 1357 Main St, St. Helena, CA 94574, USA
    While many of Napa’s other bakeries are known for their sweets, this one, with locations in Yountville, Napa, and St. Helena, is known for something entirely different: bread. In particular, the Model Bakery’s English muffins have achieved nationwide fame and appeared on Oprah’s “Favorite Things” list. The breads are so popular that you have to arrive by 9 a.m. on weekend mornings if you want them fresh. Model bakes other types of bread as well, including levain, harvest wheat, and sourdough, as well as French baguettes and walnut bread. Even the bakery’s focaccia is off-the-charts good. In addition to all these carbs, the bakery also offers hot sandwiches, salads, and pastries.
  • 1150 Queen St W, Toronto, ON M6J 1J3, Canada
    Usually, when you travel, it’s to experience a different side of yourself. The more adventurous side, the slightly less scheduled side, the sleep-in-without-guilt side. And when you stay at the Drake Hotel in Toronto, you can’t help but feel like your cooler side is making a much-needed appearance. The recently renovated property on Queen Street West features the kind of interior design that radiates style whether it’s in the kaleidoscopic lobby, the next door theater, or in two wings of suites. That’s because the hotel commissioned artists to showcase their work on plenty of open surfaces — from a black-and-white squiggle accent wall in guest rooms to personality-driven drawings in the elevator — and the results make for surroundings that are the material equivalent of black sunglasses. Paired with of-the-moment details like pink terrazzo showers and wraparound midcentury sofas, and the Drake Hotel is meant to cultivate a see-and-be-seen vibe.

    But that’s not to say that the hotel sacrifices comfort for being camera-ready. The staff is kind and always available through text, the beds are soft and squarely stationed in front of a well-appointed bar and flatscreen television, and designer toiletries are filled to the brim. It’s also possible to eat throughout the day at the hotel’s delicious cafe and patio (get the French toast), and then spend the night at its second-floor bar or ground floor lounge. On weekends, even if you’re not a guest, you can stop by for regularly scheduled events including a DJ who spins old and new tunes. If you do plan on leaving the hotel to see the city, then you’re right in the midst of it, and the surrounding neighborhood can keep you readily entertained.

    When you stay at the Drake Hotel, don’t be surprised if you feel relaxed, in-the-know, and decidedly cooler once you check out. These are sides of yourself the hotel may have encouraged, but feel free to hold on to them after you return home.
  • 34631 N Tom Darlington Dr, Scottsdale, AZ 85262, USA
    Nature may have spent 12 million years creating the rock formation that is the centerpiece of this 1,300-acre Hilton Curio Collection resort in the foothills of the Sonoran Desert, but late-coming humans have done a commendable job of adding the finishing touches. Although the Boulders, with its casita accommodations blending into the landscape, its championship golf courses, and its upscale shops, is as luxurious as any resort in the Scottsdale area, it’s also where guests are most likely to feel they are truly in the desert. An early-morning walk along groomed paths, when the first rays of light are turning the landscape golden, is as likely to produce the sounds of woodpeckers or owls calling from their nests in saguaro cacti as it is the whack of a ball against club or racket.
  • 3398 Longteng Ave, Xuhui Qu, Shanghai Shi, China, 200000
    Wang Wei and her husband, Liu Yiqian, are voracious collectors of Chinese art, both contemporary and traditional. The first Long Museum opened on the Pudong side of the river, in the suburban neighborhood of Jinqiao; the second is located on West Bund, a mere 15 minutes’ walk from the Yuz Museum. The building, done by lauded Shanghai architects Atelier Deshaus, might just stun you, with its enormous ceilings and open rooms that flow one into the other. Most exhibitions are of Chinese artwork—past shows include a retrospective of the work of cartoonist Zhang Guangyu and a selection of Qing Dynasty paintings. But big-name Western artists also show here, among them James Turrell and Olafur Eliasson.
  • 300 East New England Avenue
    Just 10 minutes from downtown Orlando, in village-like Winter Park, the Alfond Inn has a unique legacy: The boutique lodging was created to provide income for scholarship funds at neighboring Rollins College, one of Florida’s oldest liberal arts schools. If helping students isn’t reason enough to book a stay, the hotel offers lots more incentive. A skylit domed atrium in the Spanish colonial–inspired main building draws your eye to a rotating collection of artwork curated by Cornell Fine Arts Museum, and pet-friendly guest rooms are simple and cheerful. While the hotel is not a full-fledged resort, it offers guests plenty of opportunities to linger. Fire pits and rocking chairs are dotted around the property, and shaded areas for loungers enhance the rooftop pool’s already undeniable appeal. Hamilton’s Kitchen restaurant serves modern Southern cuisine paired with wines selected by an award-winning sommelier. And shops, wine bars, and independent boutiques like Rifle Paper Co. line the town’s Park Avenue, a few blocks away. You can also take a pontoon boat tour for views of many of the Mediterranean-style mansions along the waterfront. Perhaps best of all, Disney and Universal theme parks are only a half-hour drive away.
  • 360 Kangding Road
    You don’t know you need a paperweight shaped like a dumpling until you see it. Hidden behind sliding doors on an unassuming street corner in Shanghai‘s Jing’an District, Spin is the best place in the city to buy modern Chinese ceramics. The shop works with artists in Jingdezhen, China’s porcelain capital, to make original, limited-edition works of art at competitive prices, from a small porcelain and wood display table to delicate celadon-green teacups and dainty chopstick rests shaped like chili peppers. Spin ships worldwide at a reasonable cost, so you don’t have to worry about lugging a vase the size of a small child through Asia.
  • Vicolo dell'Oro, 5, 50123 Firenze FI, Italy
    A hotel with the words “gallery” and “art” in its name would be remiss not to include at least a nod to the art world in its decor (though more than a few establishments have been known to throw up a wall-sized painting by a well-known artist and declare themselves art hotels). As Florence’s pioneering design hotel, the Gallery Hotel Art doesn’t skimp. Virtually the entire ground floor, from the lobby through to the lounge and trendy Japanese-Mediterranean-Peruvian fusion restaurant, is one giant gallery, its sleek white decor acting as the calming, understated counterpart to the contemporary art and photography not often found in this city.

    Indeed, don’t underestimate the groundbreaking nature of this hotel. Design hotels may be a dime a dozen these days, but when the Ferragamo family’s Lungarno hotel collection launched with this modern getaway designed by Michele Bönan, its clean-lined furnishings and chrome, white, and natural wood hues were a challenge to a city outfitted in rich brocades and dark wood antiques. As such, the Gallery Hotel Art isn’t the flashiest stay, but it is the kind of place you can relax and unwind and feel like you aren’t living in the Renaissance days.
  • Via della Scala, 18, 50123 Firenze FI, Italy
    Hundreds of years ago, at the height of Florence’s Renaissance heyday, visitors to this cultural capital wouldn’t have stayed in the kinds of luxury hotels that now line its picturesque streets. Rather, the well-heeled would have come at the behest of friends, lodging in private homes whose unassuming facades in the best neighborhoods belied their sumptuous interiors and private gardens, outfitted with art and artifacts collected from around the world.

    A guesthouse to its core, Casa Howard continues this Florentine tradition; there is neither lobby nor restaurant, and the owner Massimiliano Leonardi di Casalino lives in his own apartment here while in town (note, it can be rented when he’s away). Jennifer Howard Forneris, one of the design-conscious proprietors who has since passed away, was the daughter of renowned textile designer Luciano Forneris. She gave each room its own look, with finds from her and Leonardi di Casalino’s world travels. A media room is the sole common area, and a hammam steam room and an on-site concierge service are the only nods toward traditional hotel services. Insider recommendations are personalized according to guests’ preferences, and the honor bar feels more like a friend’s (well-stocked) fridge.
  • Calle Vallaresso, 1323, 30124 Venezia VE, Italy
    The Bellini was born in Venice at Harry’s Bar, which has been hopping since 1931. Declared a National Historic Monument by the Italian government in 2001, this San Marco bar and restaurant is a cultural institution. Even though it doesn’t do the best food in Venice, and prices are ridiculously expensive, it’s worth dining here once just for the experience. Over the decades it has served a global collection of writers and artists, including Ernest Hemingway, Charlie Chaplin, and Orson Welles, and today it’s still popular with Venetian movers and shakers.

    The interior decor has not changed since Giuseppe Cipriani opened Harry’s on the eve of World War II (and during the war, Harry’s was one of only a handful of restaurants in Venice that would serve Jewish patrons). The food is classic Venetian. Try the baked sea bass with artichokes for a main, and make sure to save room for dessert. Harry’s is famed for crêpes flambées and also its Cipriani chocolate cake. Reservations are imperative; when booking ask for the ground floor because dining here is all about seeing and being seen, and the second floor is considered much less cool by Venice society (although it has much better views and more dining space).
  • 100 John F Kennedy Dr, San Francisco, CA 94118, USA
    The Victorian-era glass and wood structure, which looks like a sugar-coated castle atop a grassy slope, is Golden Gate Park’s oldest building. It’s also one of San Francisco’s most splendid historic sites. Wander through five different galleries housing 1,700 species of aquatic and tropical plants along with the world’s largest public collection of high-altitude orchids. The potted plant gallery features rare flowering plants and an assortment of decorative urns and containers from all over the world, including a leftover from San Francisco’s 1915 Panama-Pacific International Exposition. Keep your eyes open for special exhibits, including the annual Butterflies and Blooms, which transforms the conservatory into a magical garden aflutter with hundreds of butterflies.
  • Praia Castelejo, Portugal
    Each time I visit this beach, I am enchanted anew. These beautiful sands, sea, and cliffs are exotic. I sit on the sand watching swimmers, surfers, boaters, and fishermen. I watch the birds happily flying around. I stare at the brilliant blue sky with its puffy clouds gliding by. And I gape at the huge cliffs that tower over all of us.I collect the rare rocks with white stripes running through the stone that are unique to the area. This is Castelejo Beach on the western coast of Portugal where there are many rugged, wild beaches. From Lagos, you go west to Vila do Bispo and follow the signs to this beach. The road is rugged and narrow and ends just above the beach with a parking lot. Get a good map of the area at your hotel. Hungry? The Castelejo Restaurant is at the top of the path to the beach. This restaurant serves octopus dishes and other fresh seafood. If you are there at sunset you will be lucky enough to see this gorgeous beach bathed in glowing light. Try to visit this beach when in the western Algarve.
  • 1354 Kuhio Highway
    In the heart of old town Kapaa, the Olympic overlooks Main Street with laid-back Hawaiian style. Upstairs in an old building that’s been converted into a collection of ragtag shops, the cafe has a commanding presence. Park and wander along the street to make your way to the stairs leading up to the bar and cafe. No pretense upon arrival. The tables lining the open windows in front are choice for people watching and catching the breeze from the prevailing trades. Late afternoon sun streams in and heats things up but is a welcomed delight. There’s always something cold close by to help with the temperature regulation. The bar is a mix of locals and tourists. Happy hour is a draw from four to six with discounts on drinks and select appetizers. I’m a big fish fan when near the source and the fish tacos at the Olympic take the gold. Dressed with a mango salsa and sides of beans and rice, they use two kinds of fish to keep your tastebuds guessing. There is a good selection of island beers and all the fruity umbrella drinks you can imagine. It’s right on the Kapaa multi-use path, so you can cruise in on your beach bomber for a refreshing break. Staff are friendly and service is casually good. Worth a stop when trolling around Kauai for someplace to take a break from vacation.
  • 11 Rue des Gravilliers, 75003 Paris, France
    Among the increasingly trendy streets of the Upper Marais, this intimate hotel offers a refreshingly low-key place to unpack. Named for the classic Francois Truffaut film, and set in a former precious metal factory, Jules & Jim has a low-fi artistic bent. The ground-floor lobby and bar—both set off a central, glass-roofed courtyard and garden—feature a rotating collection of works by local painters, photographers, and graphic artists, as well as residential-style seating and bookshelves lined with bric-a-brac. Spread over three structures, the 23 rooms range in size; the “Jules” options in the main building are the smallest and best for solo travelers, while the “Hi-Macs,” “Sous Les Toits,” and “Duplex” accommodations work better for two guests or longer stays. Some categories include perks like terraces, sofa-beds, Nespresso machines, and views of Montmarte, but all come with Bluetooth sound systems, free Wi-Fi, rainfall showers, and access to 24-hour room service (note that there are no mini-bars or fridges).