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Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

When the Four Seasons took over Johannesburg‘s celebrated Westcliff Hotel (a colonial-style grande dame that was admittedly fraying around the edges), its brief was clear: update the tired ambience with a cutting-edge makeover. For its first property in South Africa, the luxe hotel group spared no expense, closing the hotel down for a year and a half until they were satisfied with the full revamp, which debuted in December 2014. The new Four Seasons has modern elegance in spades, from the minimalist View restaurant (the main feature here is, as the name suggests, the panoramic view over Johannesburg’s lush landscape) to the 117 rooms outfitted with chrome details and local contemporary art.

For generations, the Westcliff has been the bastion of Johannesburg’s most rarefied citizens, who decamped to the hotel for special occasions or met for high tea on the terrace. With its new look, the property is ready to welcome back its longtime clientele while opening doors to a more youthful set in the process.

For authentic souvenirs from all over the world, head to the West Side Bazaar. The incubator on the Grant Street Corridor supports refugees, immigrants, and low-income entrepreneurs on their path to becoming successful business owners, providing them space to pursue their dreams. Start in the stalls, where you’ll find everything from Rwandan peace baskets and Burmese puppets to Sudanese jewelry and macramé art by an Iraqi woman named Nadeen Yousef. Afterward, refuel with your choice of Mexican cuisine, Asian snacks, Ethiopian fare, halal food, and more.

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.

Latitudes is the acclaimed restaurant at the Sunset Key Cottages, on Sunset Key, a small private island accessible only by boat. Take the ferry across the Key West Harbor—your scheduled ferry time is your reservation time. The dreamy ride across the gulf waters sets the tone for the rest of the evening. While most restaurants in Key West have flexible dress codes, if any, Latitudes is a place you should break out the nice clothes. If the weather’s nice, ask to eat on the patio, which is decorated with twinkling lights wrapped around the green palms that surround the courtyard, and features tables set with white cloths and candles.

It was Christmas Day, and the fastest route from Bakersfield to Morro Bay. The route that didn’t involve freeways. {We like that.} So we headed west on Highway 58, through the otherworldly power stations and desolate cotton fields of Rosedale and then up and up and up til we could gaze out over the cold green hills. The winter-dry grass waved in a bitter wind, snow dusted across distant mountain tops. We danced in place, to keep from freezing. A remote and winding road, this one reminds you that even central California has hidden pockets, little spaces where you might, maybe, just vanish.

Philadelphia locals who love the outdoors are particularly fond of walking, jogging or biking the scenic 8.5-mile riverfront “Loop”. The Loop is what we call the recreational path that runs from near the Art Museum to the west side of the Schuylkill River on Martin Luther King Drive, then crosses the Falls Bridge in East Falls, and continues along Kelly Drive back to Boathouse Row, Lloyd Hall and the Art Museum. (Or it can be done in the reverse.) One of the best things about this route for cycling or jogging is that Martin Luther King Drive is closed to vehicular traffic from 6 am to 5 pm on Saturdays and Sundays from April through October. (A small portion of the road from Eakins Oval to Sweetbriar Drive re-opens to traffic at 12 noon.) Bike rentals are available from Wheel Fun at Lloyd Hall. The view of Boathouse Row above is just one of many scenic views from Martin Luther King, Jr. Drive (formerly known as West River Drive) on the west banks of the Schuylkill.

When you’re ready to call it a day on the slopes, take Park City Mountain Resort’s Quittin’ Time run down to High West, the world’s only ski-in gastro-distillery. Tour the space, then try the 36th Vote Barreled Manhattan, made from a pre-Prohibition cocktail recipe that calls for aging the drink for 90 days in white oak barrels. The food goes down pretty easily, too: A bowl of elk chili will warm you right down to the toes of your ski socks. For lighter fare, the popcorn tossed with bacon, caramel, and cashews is sweet, salty, and a nice counterpoint to a glass of double rye.

The city’s most famous snowbird, architect Frank Lloyd Wright, spent winters at his home and architecture school in the Sonoran Desert. Taliesin West brings the horizontal lines and organic materials of Prairie School design to the desert landscape in low, skylighted buildings. Behind-the-scenes tours visit the pop-up structures that students have designed as living spaces amid the barrel cactus and paloverde trees.

Right on Key West’s famous Sunset Pier and next to Mallory Square, Ocean Key is at the center of the action, proven by the flocks of tourists who descend on the pier every evening at sundown. Inside the resort, the contemporary rooms are decorated in tropical colors like bright lime and turquoise, and have bathrooms with rainfall showers and whirlpool tubs and private balconies with views of the Gulf of Mexico or buzzy Duval Street. The angular pool is surrounded by cabanas and day beds; grab a ringside seat for the daily fashion show at Liquid, the kicking poolside bar. Prefer a quieter experience? The spa has a full range of treatments and packages that lean heavily on Asian traditions and ingredients, from Balinese massage to a Javanese rice-and-turmeric body scrub.

IndexG B&B was an art gallery before the owners renovated the second floor into a four-bedroom bed and breakfast. Housed on a sleepier stretch of Gladstone Avenue but close to the action of both the West Queen West and Parkdale neighborhoods, this family-run B&B offers affordable rooms and minimal amenities. Art is displayed throughout the hotel, and it is all available for purchase. With much to do in the area, this is a well-located hub from which to discover the best of Toronto.

Telluride’s literary mecca, this beloved store is stacked with more than 10,000 books at any given time. The expertly curated regional books section is a fount of the Wild West’s writing prowess, with illustrative tomes on the town’s lurid backstory (you’ll want to peruse Tomboy Bride: A Woman’s Personal Account of Life in Mining Camps of the West). When your eyelids get heavy, head to the tiny coffee bar—squirreled away at the back of the shop—for a caffeine jolt to bolster an afternoon of reading.

Dining at one of Negril’s excellent cliffside restaurants is highly recommended, and the gorgeous setting of Ivan’s Bar & Restaurant at Catcha Falling Star makes it a very nice option. The longtime favorite has one of the best views along the coast and serves lobster dinners and classic Jamaican cuisine with a bit of a modern twist. Guests are seated under an open-sided thatched roof or out under the stars at private tables on a patio near the cliff’s edge. Another favorite choice for romantic cliffside dining is the restaurant at Rockhouse Hotel. (If you want more cocktails post-dinner, walk down to LTU Pub and mingle with the locals. Casual eateries and cliff bars along West End Road include 3 Dives and Sips & Bites.)

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.

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.