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The most high-adrenaline way to see Sydney Harbour, BridgeClimb has been dressing up locals and travelers in jumpsuits and safety harnesses to ascend “The Coathanger” since 1998. Along the way, they learn fun facts about the Sydney Harbour Bridge, like how it was built using six million rivets, which bridge workers tossed to each other when they were white hot and ready to weld. You’ll also gain a new appreciation for the Sydney Opera House as well as the world’s deepest natural harbor, which just so happens to be the birthplace of European Australia. At the top, strike your favorite Zoolander pose, or try “the koala,” which Ben Stiller invented during his climb.

Pearl was founded in 1881 as a traditional brewery. These days, however, the bustling complex is less about beer than its 15 restaurants, dozen-plus retailers, and numerous family-friendly events, including a twice-weekly farmers’ market. Start with lunch at La Gloria, chef Johnny Hernandez’s nod to interior Mexico, followed by dessert at Bakery Lorraine, where you’ll find an enticing rainbow of Parisian-style macarons. If you’re in the mood to shop, pick up a tailored guayabera from Dos Carolinas, or a piece of handcrafted jewelry from Ten Thousand Villages. Pearl Brewery is even home to Hotel Emma, a true gem in San Antonio’s boutique-lodging scene, in case you don’t want to leave.

The centerpiece of Turks and Caicos is Grace Bay, on the island of Providenciales (known locally as Provo), where the miles-long sugar-sand shore routinely tops “best beach” lists for the Caribbean and the world. The inland area along this stretch of northern shoreline is where you’ll find most of Provo’s hotels, shopping, and restaurants. Grace Bay is part of the Princess Alexandra National Park. It has calm waters and a sandy seafloor with no rocks or corals to step on, making Grace Bay the perfect place for swimming, splashing along the shoreline, parasailing, and stand-up paddleboarding.

Sustainability is the name of the game at h2hotel in downtown Healdsburg. The building is certified LEED Gold by the U.S. Green Building Council and has a living roof of grass and succulents that filters rainwater to reduce the impact on Healdsburg’s storm-drain system and neighboring Foss Creek. Inside the 36 rooms, sensors turn off lights, fans, and air conditioners when guests leave, and the bamboo flooring is layered with fair-trade, chemical-free rugs. Even the way the hotel approaches in-room beverages is green; instead of plastic water bottles, guests are given recycled glass wine bottles to refill at water stations around the property (there’s at least one on each floor). The hotel isn’t only eco-friendly; it’s swanky, too. Out back, along Foss Creek, a lap pool is an inviting spot to spend a hot and sunny afternoon. In the lobby, the bar at Spoonbar! Restaurant still turns out some of the tastiest craft cocktails in town. All overnight stays include complimentary breakfast and access to the hotel’s collection of Public bikes. There’s also a free yoga class for guests every Sunday morning. Be sure to see the on-site Hand Fan Museum, a passion project for Pam Sher, the matriarch of the family in charge. Also make time for a meal at Oaxacan restaurant Mateo’s Cocina Latina across the street (chef Mateo Granados is married to the owner of the hotel).

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.

A honeymooner’s dream, the 40-acre Grand Wailea hails from the era of the Hawaiian mega-resort. From its perch over the Pacific, the hotel offers an impressive collection of original art (much of it created by locals specially for the property), 40 acres of lush tropical gardens, and over-the-top water features among the nine swimming pools, including slides, caves, a Tarzan swing, swim-up bars, and a canyon with an enclosed “lava tube.” The resort even boasts Humuhumu, a Hawaiian-inspired restaurant set in a man-made lagoon, and 780 guest rooms, all of which include a private patio or balcony. Opt for accommodations on the Napua Club level for a more intimate “boutique hotel within a resort” feel.

Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.

A historic property, Hiiragiya has hosted many a notable writer, artist, celebrity, and imperial family member since its opening in 1818. Operated by the same family for six generations, the ryokan is steeped in centuries-old tradition, etiquette, and service, with the aim of making guests feel at home during their stay. Rooms are spread across two buildings—the original with its classic style, and the newer, sleeker wing, where the color palette is a bit brighter and the windows and doors are more modern. Both feature updated amenities, however, including flat-screen TVs, minibars, and free Wi-Fi. Among the hotel’s other highlights are the kaiseki-style meals, during which kimono-clad guests enjoy course after beautiful course at low tables. Breakfasts and dinners are both included in your stay, and feature seasonal bites served in locally made lacquerware bowls and boxes.

Hilton Molino Stucky on Giudecca Island is a zippy five-minute boat ride (free for guests) away from bustling Piazza San Marco, and ideally located for those craving a tad more tranquility without missing out on any of those sweeping Venetian vistas. Once a working flourmill, this brick, industrial-era fortress has been reimagined as a luxury hotel with all of the modern bells and whistles. Take a break from museum hopping with a day spent surveying the city below from the city’s only rooftop pool (followed by quality time spent in the spa). Of course, with several dining options just steps from your room, you could happily spend most of your time right here.

If mixing business with pleasure, this hotel—with Executive Suites, a ballroom for events, several conference rooms, and a business center—makes for a superbly scenic day at the office.

The bustling corner of Walnut and 17^th streets is anchored by the Latham, a stone-and-brick tower built in 1907 as luxury apartments for moneyed Philadelphians. While other Center City historic structures met their demise in the late 1960s, a group of investors doubled down on the stately building, transforming it into Philadelphia’s premier business hotel in 1970. The prestigious address completed a top-to-bottom renovation in 2011, bringing the Latham firmly into the 21st century while preserving period artifacts and style.

True to its apartment roots, arriving at the hotel is more like entering a tony doorman building, and the Latham’s residential roots bestow spacious guestrooms with tall ceilings, bay windows, and big bathrooms. Gold and gray hues are complemented by pops of blue, while big bathrooms keep it simple with a tub/shower combination.

The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).

One&Only Royal Mirage, the calmest and most elegant of Dubai’s mainland beach resorts, consists of three Arabian-styled palace hotels set amid a lush, 65-acre palm garden fronted by a three-quarter-mile white-sand beach. The Palace, the oldest and largest hotel, still has the feeling of an intimate escape despite the past decade’s frenetic high-rise construction along the coastal highway. The Arabian Court draws local couples and, in winter, sheikhs who take trained falcons to tea in the lobby. The most exclusive joint, the Residence, is closest to the spa where guests indulge in massage-themed vacations. All rooms share a French-Moroccan decor and courteous staff who continually offer fruit skewers, cold towels, and drinks around four of the U.A.E’s most beautiful outdoor pools.

A delightful peach-colored villa set directly on Treasure Beach, this Jamaican-owned guesthouse is a gem, and feels more like a vacation home than a hotel. There are six spacious guest rooms and two larger suites, each with their own patios or balcony with a glorious sea view. The interior is intricately decorated with carefully chosen African-themed paintings and sculptures, and the owner—who returned after many years in the US—takes pride in providing true Jamaican hospitality. There’s a bar and no restaurant on site, but that doesn’t prevent the large kitchen and staff cook from taking your daily orders for breakfast and dinner, dishing out excellent local specialties that are served poolside with the sea in front of you. It’s one of my favorite places to stay and get away from it all.

A massive stretch of soft white sand calls you to the Caribbean at Cancún’s largest public beach, a quiet spot amid Hotel Zone resorts. The waves can be a bit rougher than elsewhere, so it may not be great for swimming, but the strand is one of the city’s few surfing spots. Playa Delfines also goes by the name El Mirador, thanks to its spacious hilltop deck overlooking the ocean and hotel skyline and its large, colorful “Cancún” sign that’s perfect for photo ops. Among the other welcome amenities: restrooms, a playground, small shady palapas, and an outdoor gym.

You can’t go wrong with any of the Intercontinental David’s rooms, all 555 of which look out onto the Mediterranean, but those seeking the ultimate view should at least consider the Jaffa Suite for its privileged perspective on Old Jaffa, or the Tel Aviv Suite, where the panorama includes Jaffa, Tel Aviv, and the sea. On the other hand, this hotel is so centrally located that you could simply walk to anything you want to see, from the evocative old city of Jaffa with its minarets, stone walls, and bobbing boats, to the Neve Tzedek district full of bohemian cafes and boutiques. Although you’ll be tempted to fill up on produce, halva, and pastries at the nearby Shuk HaCarmel market, save room for at least one dinner at the Intercontinental David—especially the traditional Shabbat meal that takes place in the third-floor Jaffa Court on Friday nights.