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Lanai, a sleepy, 140-square-mile former pineapple plantation, is suddenly in the spotlight. Following the island’s purchase by tech billionaire Larry Ellison in 2012, the bay-facing Four Seasons Resort Lanai underwent a multimillion-dollar overhaul that reduced the number of guest rooms from 286 to 213. The rooms shook off their dated look with mahogany floors and walls clad in slate and teak. Guests can dine at outposts of Nobu and Los Angeles–based Malibu Farm, take private flight lessons and horseback-riding excursions, or book one of the resort’s wellness-focused retreats.

Chef Jorge Vallejo spent time in the kitchen at Pujol before he and wife Alejandra Flores opened Quintonil, giving the former boss a run for his money. Their place, too, has become a fixture on best-restaurants lists, and is changing how people understand Mexican food. Taking its name from a weed that not long ago “decent” Mexicans wouldn’t dream of eating, Quintonil seeks to rescue and preserve discarded Mexican ingredients—particularly heirloom vegetable and herbal varieties—as part of the progressive and sustainable eating program it so elegantly advocates. Menus change seasonally, but a recent bill of fare included an avocado tartare with ant eggs and quelite-herb chips; chilacayote squash in mole with basil; and a rich chocolate-and-pinole-flour parfait. A tasting menu of Neronian proportions is also available.

Take the Incline Railway up Lookout Mountain on your way to Ruby Falls and Rock City and you’ll understand why the journey is often half the fun. In operation since 1895, the funicular has a maximum grade of 72.7 percent, making it the world’s steepest passenger railway and earning it the nickname “America’s Most Amazing Mile.” For its age and impressiveness, the railway is now a designated National Historic Site and a Mechanical Engineering Landmark. Before your ride, visit the machine room to see the enormous gears that drive the train, then sit back and enjoy the sweeping views of the valley below as you creep steadily up the track. Sure, you could just drive to the top of Lookout Mountain, but where’s the fun in that?

Laguna Beach’s deep connection to the arts goes back to 1918, when 150 local creative residents started the Laguna Beach Art Association (the city’s population was only 300 then). That association went on to launch what’s now the Laguna Art Museum. Although the museum covers countless genres and eras, there’s one thing every piece has in common: They’re all made in California. The 3,500-strong permanent collection spans the early 19th century to present day, from light and space installations to pop art (and also includes pieces by art-world stars like Ed Ruscha and Wayne Thiebaud). It’s rounded out by a handful of new California-centric exhibitions each year. Highly knowledgeable docents—all have completed an extensive nine-month training course—lead lively one-hour walk-throughs at 11 a.m. Friday to Tuesday; groups of 10 or more guests may book guided tours in advance. Must-do: Hit the museum on a Thursday night when it stays open until 9 p.m. and becomes a community hub, with lectures, film screenings, and live concerts in the galleries.

Housed in a low-rise building on one of Austin’s trendiest streets, the South Congress Hotel is much more than just a place to stay. The boutique hotel is practically a neighborhood unto itself, complete with everything from stores and a nail salon to two restaurants, a coffee shop, and an all-day café. Done up in denim, leather, concrete, and wood, the 83 guest rooms feature Matteo bed linens, rainfall showers, and Apple TVs, plus fun extras like C.O. Bigelow bath products, Finery LA robes, and locally sourced minibars. Guests even enjoy exclusive streaming access to more than 40 movies from Drafthouse Films, a production company based in Austin. For when—if ever—visitors want to leave their rooms, the hotel also features a rooftop pool and bar, as well as a prime location near some of the city’s coolest shops, restaurants, and music venues, which are easily reached thanks to amenities like BMW X5 house car service and Faraday electric bike rentals.

When the Hôtel du Vieux-Québec poured nearly $3 million into renovating what was once an 18th-century nunnery in 2014, it was already recognized for its green leadership and sustainability: it’s the only carbon-neutral hotel in the province and the only one in Canada to use 100 percent biofuels. Today this boutique property on Rue Saint-Jean, convenient to all old-city attractions, furthers its ecocommitment with features like rooftop gardens that not only grow organic produce for its clients and employees but help with cooling. The hotel keeps five beehives as part of the Urban Honey Project, which helps pollinate city gardens, and the honey is used at the hotel restaurant. All of the 45 rooms and six apartments are unfussy yet comfortable, and even standard rooms have mini-fridges and a work desk. Guests are particularly fond of the continental breakfast basket that’s hung from your door each morning (so long as you book directly through the hotel) and the espresso maker and fresh fruit available anytime in the lounge.

Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.

A must-stop on the traditional handicraft circuit, this massive market—stretching four city blocks in Miraflores!—is home to stall after stall of kitschy bric-a-brac, pre-Columbian–style pottery, alpaca everything and an endless array of Andes-inspired arts and crafts. Come and shop around.

Even a Brussels native would be forgiven for thinking, at first glance, that the Dominican is a historic building. After all, the façade incorporates many of the features that existed when renowned 19^th-century French painter Jacques-Louis David lived at this address. And, inside, the site’s former incarnation as a 15^th-century Dominican monastery appears in such details as the courtyard colonnade and original stone floors in the serene Monastery Corridor. The soaring ceilings, oversized windows, and ornate ironwork of the Grand Lounge and its adjacent bar call to mind the grand cafés of early 20^th-century Europe, while rooms are adorned with vibrant paintings of classical subjects, like those by David and his contemporaries.

As historic as it all is, though, there’s no doubt that the Dominican is a modern hotel. The contemporary decor harmoniously complements its surroundings, and each of the 150 luxurious rooms has been individually designed. Many afford views of the impressive La Monnaie, the city’s opera house, located next door. The lounge is one of Brussels’ hottest spots for everything from power lunches to date nights, and the gym even has a private boxing room.

On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

The salmon-colored stucco buildings comprising the Elliott House Inn have a long history that runs parallel with the city’s. Built in the aftermath of a citywide fire, the property’s main structure was then shaken in an 1886 earthquake (the characteristic Charleston earthquake bolts are visible on the building’s facade) and battered by 1989’s Hurricane Hugo. The bed-and-breakfast reopened in 2011 after two years of renovation and redecoration, reinventing itself yet again. The main building is a classic Charleston single house, built with its narrow end on the street and a long piazza running along its length.

The rooms, with their botanical prints, hardwood floors, and Oriental rugs, are traditional in a way that’s elegant and charming rather than fussy. Rooms are available both in the main house and the single-story building across. The quiet courtyard provides an oasis from the city streets with its wisteria-dotted pergola and light-draped palmetto trees.

Opened in time for the 2000 Sydney Olympics, the Establishment is a pioneering 31-room boutique hotel housed in an 1890s steel plant near the modern-day stock exchange building downtown. Managed by the hospitality group Merivale—which started as a fashion house specializing in fascinator hats and mini skirts—the hotel is popular among brand executives who book the 328-square-foot Loft Penthouse for product launches and photo shoots. Rooms feature wood furnishings, swinging metal doors, animal hides, and suedelike daybeds as well as such amenities as Apple TV, Bose surround sound, and Lululemon yoga mats. Bathrooms are particularly luxurious here, with marble floors, freestanding tubs, Bulgari products, and tall windows that open up to Sydney’s bustling business district. The best part about the Establishment, though, is the internal access it offers to some of the city’s hottest bars and restaurants, which are housed within the same complex as the hotel. And after enjoying live music and a few stiff cocktails at the speakeasy Palmer & Co, guests are welcomed to bed with Sleep Tight tea and a homemade chocolate chip cookie.

When the swell is up and the waves are high, Sunset Beach is Surf City, UAE. Count on left-breaking waves at the Jebel Ali end and right-breaking waves at the northern tip of the beach. In between, expect a busy beach full of tourists, locals, and expats soaking up the sun. Palace Beach offers easy access to the waterways of the Palm Jumeirah (perfect for kayakers and stand-up paddleboarders), a glimpse of the great sail of a building that is the Burj Al Arab in the distance, sugary white sand between the toes, and crystalline water all the way to the horizon. If you forgot your water-sports equipment at home, Club Joumana at the sprawling JA Jebel Ali Beach Resort rents it all—from Zapcat inflatable racing boats to paddleboards.

Situated to the south and east of Lake Hoan Kiem, the French Quarter has a different feel from the rest of Hanoi—one characterized by a profusion of space. The French began shaping this part of the city in the late 1800s (in part by knocking down Vietnamese buildings and monuments), and by the early 20th century had firmly established their imprint. Today, the district retains the broad avenues, wide sidewalks, and colonial architecture from the era of French rule. Highlights include the Sofitel Legend Metropole, with its distinctive white facade and green shutters, and the iconic Hanoi Opera House, modeled on the Palais Garnier in Paris.

Every city has a building with great views and Chicago’s most famous is the 103rd floor of the Willis Tower. But a little Chicago secret is that the John Hancock building has better views and their Signature Lounge on the 96th floor has free admission so you can enjoy a cocktail while you take in the sights! My favorite time to visit is late afternoon for a happy hour Old Fashioned while the sun sets and the Chicago lights start to sparkle. It’s a great place to take visitors, it’s a great place for tourists, it’s a great place to start or end an evening but I wouldn’t bother with the food, which is overpriced for the quality and selection. The drinks are pricey but the view is truly worth it.