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On a promontory within Bouddi National Park, overlooking a secluded bay and a short walk to an empty rust-red beach, Pretty Beach House lives up to its (classically understated Aussie) name. It’s hard to believe this intimate retreat is only a 90-minute drive from Sydney city center. Its location is spectacular and historic—spot the 2,000-year-old Aboriginal rock drawings on a nature walk nearby.

There are four guest pavilions, each outfitted with wood-burning fireplaces, deep-soaking clawfoot tubs, and sun-drenched decks overlooking Broken Bay and Angophora treetops (three have their own private plunge pools). Dining is included in the stay, and it’s exceptional: Celebrated chef Dean Jones takes freshly caught seafood and local produce and crafts them into modern Australian dishes, which you can enjoy anytime you like in the Beach House’s safari-chic dining room or poolside beneath the shady gums.

Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).

As the name suggests, this hotel’s personality is one part laid-back Californian, one part British aristocrat. Nowhere is that clearer than at the 10th-floor rooftop pool, where plantings inspired by formal English gardens stand out against a backdrop of palm trees and sunny views of the Hollywood Hills. Downstairs, the London Bar channels both influences, too, with an orangeries-style latticework frieze inspired by English conservatories along with a living wall of exotic plants and a menu that ranges from classic (Moscow Mules, Pimm’s Cups) to creative (the Winston Churchill made with Bulldog gin and Laphroig scotch is a favorite).

For a true taste of local life, head to Bodden Town—the Caymanian capital before George Town rose to prominence in the 1800s—and pull over at the roadside fish fry where the likely queue tips you off to the impending tastiness: Grape Tree Café. Granted, on any given day, the crowd may include as many chickens as humans (the former seem to love nothing more than strutting from palm-shaded table to palm-shaded table on Grape Tree’s patch of beach sand). Atmosphere aside, the big lure here is the array of fried fish: snapper, mahi-mahi, swai, and wahoo—served with fritters, cassava, sweet potatoes, and breadfruit.

The 17th-century estate where Simón Bolívar died in 1830 is the site of several Bolivar monuments as well as an art museum featuring works by Latin American artists inspired by Bolívar, the hero who freed Bolivia, Colombia, Ecuador, Panama, Peru, and Venezuela from colonial rule. The estate serves as the city’s botanical garden, also worth your time for its magnificent, centuries-old trees.

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?

Captured this sunset as we drove back to our lodge, Wuksachi Lodge down the General’s Highway. I’ve been to both Yosemite and Sequoia National Parks and while I love Yosemite, I might appreciate Sequoia just a bit more because of its remoteness and the solitude that it can afford. There were far fewer people in Sequoia than Yosemite. I also enjoyed the hiking more in Sequoia than I did in Yosemite. The sequoias there are definitely worth the trip and Moro Rock is a treasure.

The path to Terre-de-Haut’s Pompierre Beach, the most beautiful on Les Saintes, leads you through a dense labyrinth of gigantic coconut trees where goats quietly graze and stroll. Up front awaits a wide stretch of golden and white sand and a sea ideal for swimming. It’s a popular spot but it never feels crowded because of the ample space. Bring your snacks to enjoy on the picnic tables at the back.

I’m not sure at what age humans develop the skill to stand still and appreciate scenery, but based on a scientific survey of kids who live in my house, it’s not age seven. (On a trip to the Canadian Rockies, as my wife and I snapped photos of the relentlessly picturesque mountains, my son, Luke, investigated how quickly he could break his toy helicopter.) Luke expects Mother Nature to be his playmate. At Bandelier National Monument, about an hour’s drive from Santa Fe, New Mexico, she is. The visitor center offers kids a booklet of activities that, when completed, earn them a Junior Ranger patch. (You could call it a bribe. We prefer the term incentive.) The scavenger hunt sent us off on the Main Loop Trail in search of birds, trees, and bugs, as well as the feature that sets Bandelier apart and makes it perfect for kids: cave dwellings. Ladders of salvaged wood lead to rooms that the Pueblo people carved out of the cliffs here over 800 years ago. “I don’t want to go up, Daddy,” Luke said. “It’s too steep.” “You’ve got this, buddy,” I said. “Just take it slow.” There were no lines of impatient parents pushing their children to race up the ladder. (We saw no more than 20 people on the trail.) Luke could climb the rungs at his own pace. He paused in triumph at the top, then set off to wander the caves. While Mom and Dad squatted—“Watch out for your bald head, Daddy”—Luke could explore without even hunching. After about 45 minutes, we were walking back toward the visitor center. We crossed a nearly dry creek by hopping hand in hand from one downed log to another and were back in time for lunch, before hunger, fatigue, or boredom could set in. It was a parent’s—and child’s—dream hike. This appeared in the August/September 2014 issue.

Vancouver’s most famous urban space, the thousand-acre Stanley Park, epitomizes everything that locals here love about the outdoors, and visitors have many ways to explore the expansive grounds. Hiking trails weave around totem poles and hemlock trees, while at the beaches, you can swim, people-watch and picnic. Rent a bike or a pair of in-line skates for a scenic ride along the Seawall, or wander through the many gardens where rhododendrons, azaleas and roses bloom.

About an hour’s drive south of Barcelona, past scruffy beach towns along the Costa Dorada, Le Meridien Ra Resort and Spa stands out from its neighbors on a beautiful length of the Mediterranean. Inside the resort gates, an elegant central building, buffed out for the 21st century, does not fail to impress. Originally built as a tuberculosis hospital for children, the hotel has turned its focus from illness to wellness: A three-story modern addition contains the Explore spa, with treatments ranging from all sorts of massages and facials to ayurvedic experiences and thalasso body masks with iodine-rich algae. After treatment, clients are encouraged to prolong the self-care vibe with a visit to the roof, where an indoor-outdoor complex offers glamorous sun beds on a deck, steam and sauna rooms, as well as a pool with stations for bubble jets of varying intensities as well as shoulder-massaging water spouts and soothing currents. Guest rooms are spacious and cleanly modern with midcentury design touches (an angular sconce beside the bed, a curvy Hans Wegner-inspired chair and stool) and a mild color palette. Generous cabinet space speaks to the resort’s summer season—many repeat guests come for a week or two. (For additional space, families can opt to rent one of the on-site apartments.) The resort’s kitchen, which draws inspiration from Catalan traditions, is inventive and playful, employing some molecular gastronomy techniques without any fussiness. Small dishes—accompanied by tiny pearls filled with local vinegar or topped with foam or served in paper cones—are perfect for summer appetites (and can be augmented by more traditional seafood, fish, and ham dishes). The beach itself is a wide, sandy stretch planted with a few palm trees and several rows of beach loungers and umbrellas. Beach servers ferry food and drink from the airy dining pavilion, and a masseuse offers complimentary chair massages. The Mediterranean here, a vivid blue, contains 10% more iodine than elsewhere—a health benefit espoused both by the religious order who ran the sanitarium and by the resort now. As a brand, Le Meridien supports local arts and culture and this hotel is a bright example of that ethos: among many offerings, it hosts literary festivals, visits to the nearby studio of a ceramic artist, cooking lessons on the nuances of Catalan rice dishes, winery tours, live music in the gardens, and is home to four grand bronze sculptures by Salvador Dali. But for all these options, days can pass lazily, too, with a lunch under the grape arbor, or a round of backgammon on the shady terrace facing the beach, accompanied by a glass of rosé. ¡Salud!

It took a 1920s cotton magnate and a 1980s oil heiress to create the city’s most iconic stay, the former incorporating hallmarks of European design into a 10,000-square-foot house the likes of which had never been seen in Dallas—think Italian marble columns, 19th-century Spanish cathedral doors, and a ceiling inlaid with 2,400 separate pieces of wood. The latter transformed it into the Mansion Restaurant, which remains an award-winning favorite, adding a new wing with 143 guest rooms and suites and establishing the first property in the now-global Rosewood chain. Past the signature peach facade, the since renovated accommodations mix modern technologies with gracious amenities, historic touches, and residential-style décor—a combination that’s proved a hit with visiting dignitaries, international business travelers, and privacy-seeking celebs. A small pool, fitness center, and massage treatment rooms round out the facilities in the new wing, while meeting rooms and event spaces are located in the mansion’s gorgeous former living quarters. Young professionals flock to the leather-walled Mansion Bar for after-work craft cocktails and live music on weekends, while the brunch crowd heads to the Terrace restaurant to dine around outdoor fireplaces and oak trees hung with lanterns. Just don’t pass up ordering the legendary tortilla soup at The Mansion.

You will likely see Bronzino’s famous portrait of Eleonora (or Eleanor) de Toledo, in the Uffizi, during your visit to Florence. The Spanish noblewoman who became the duchess of Florence in 1539 when she married Cosimo I de’ Medici was unusual for her time, playing an active role in politics and as a patron of the arts. Her patronage extended to garden design, in its infancy (at least in Europe) in the 16th century. Eleonora commissioned the Boboli Gardens behind the Pitti Palace as a green escape from the city; they continue to provide a retreat for travelers today.

Among the earliest examples of the formal compositions that would dominate garden design through the 20th century, the grounds are dotted with classical statues and fountains while straight axes run up and down the hillside with an apparent disregard for topography. A moment in design history can be experienced first hand here. There’s a feeling that the man who planned the gardens (Niccolò Tribolo) conceived a formal plan and then simply laid it atop the site. Principles of garden design were later to shape city planning. The allées of the Boboli Gardens were early models for grand boulevards leading the eye to distant monuments. One of the pleasures of gardens, however, is that you don’t need to know their histories to enjoy the flowers in bloom or the sounds of birdsong and splashing fountains.

A compound-like hideaway on a leafy street a block from trendy South Congress Avenue, Hotel Saint Cecilia is a retro-glam love letter to the 1960s and ‘70s rock music scene, named for the patron saint of music and poetry. But that doesn’t mean that rock stars smash guitars and throw ragers here (unless they rent out all 14 rooms, of course); unlike at its nearby sister properties, Hotel San José and Austin Motel, only guests and club members are welcome at the lounge, a laid-back affair with a Parisian-café–style patio, chesterfield sofas and a fireplace indoors, and craft cocktails and gourmet small plates. Between the 1888 Victorian main house—originally inhabited by a descendent of Davy Crockett—and verdant grounds that hide private porches and a serene pool, the hotel feels more like an impossibly stylish artists’ retreat than a celebrity getaway.

Each distinctively decorated room is larger than many an apartment, and seems ripped from the pages of a fashion magazine photoshoot. Every detail has been thought through, from the refreshing Grown Alchemist body care products to the Swedish Hästens mattresses (the hotel is the only one in North America with them in all rooms) to the impressive library of LPs to borrow. Everyone’s a rock star, here.

Washington Square Park is only a fraction of the size of Central Park, but it is as almost as much of an icon of New York as its much larger counterpart uptown. It’s likely because it sits in the heart of Greenwich Village, and has thus served as a backdrop for many events in the city’s history. In the late 19th century, it was one of New York’s most fashionable addresses (that period was captured by Henry James in his 1880 novella Washington Square, later the basis for The Heiress, a play that was also adapted into a movie). The arch along its northern side dates to 1892 and was designed by Stanford White to replace an earlier one, in wood and plaster, erected in 1889 to mark the centennial of George Washington’s inauguration. When Greenwich Village became the haunt of artists and writers, the park was a green space for the city’s counterculture; folk singers and street performers are still a common sight, and the park is also frequently used for political protests and rallies. On sunny days, especially during the academic year, the park is filled with NYU students, neighborhood residents, and tourists taking in the scene.