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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.

In 2012, one of the world’s richest men—Oracle founder Larry Ellison—bought 97 percent of the island of Lanai. The single sweeping deal (reputed to cost $300 million) included the exquisite Four Seasons Resort, overlooking a marine reserve. The resort’s dining experience par excellence is Nobu, where celebrity chef Nobuyuki Matsuhisa presides over the perfect marriage of Japanese dishes and Peruvian ingredients. Kick things off with crispy Brussels sprouts or scallops with jalapeño salsa, then move on to sushi, hand rolls, or Wagyu beef. Save room for the Bento Box dessert with green tea ice cream and chocolate flourless cake. Or go old-school, if it’s on the menu, and order the mochi pound cake backed by yuzu-cherry jelly and peanut butter ice cream.

Built in 1906 as a private residence and converted in the 1950s, Rosedon Hotel is a low-key alternative to Bermuda’s pricey chain hotels. Despite being located in the bustling heart of Hamilton, the property’s lush tropical gardens have the feel of a country estate where geraniums always seem to be in bloom and balmy breezes waft through elegant, colonial-style rooms. The 40 individually appointed accommodations have enough chintz to please a dowager aunt, plus iPod docking stations and private balconies to satisfy everyone else in the family. Laid-back pleasures await in the public spaces: sample weekly changing finger sandwiches during afternoon tea or dine on fresh-caught specialties at Huckleberry, the on-site restaurant, or simply lie in the sun on one of the white chaises that surround the small pool. Though the resort doesn’t have a beach of its own, a free shuttle is on hand to take you to pink-sand shores nearby.

Even during Antigua Sailing Week, when English Harbour is chock-a-block with yachts from all over the world, the 28-room Inn at English Harbour remains serenely detached from the chaos. The inn is five minutes by water taxi from the center of things at historic Nelson’s Dockyard, but its tucked-away location on a white-sand beach backed by 19 leafy acres (and a no-kids-under-10 policy) ensures tranquility. Four snug rooms, with marble floors and queen beds, occupy two beachside cabanas, while 25 more generously proportioned suites, all with dark mahogany floors, four-poster king-size canopy beds, and verandas or balconies, are in three wooden buildings sitting farther back among the tropical greenery. Although the Terrace Restaurant and Stone Bar are in the property’s original stone house, the rooms, despite their colonial look, are relatively modern, which means there is a flat-screen TV, an iPod docking station, and Internet access.

One of my favorite spas in Jamaica is located at the well-known Jakes Resort, in Treasure Beach. Small, cozy and away from the big resort towns, it’s a wonderful place to unwind. Opt for a long full body massage in one of only four oceanfront treatment cabanas, with doors open on the sea ahead. The spa prides itself in using fresh ingredients from its on site gardens. When you’re done, walk over to Jack Sprat for a quick bite with a view and take a nap on the beach—not necessarily in that order.

Mission Dolores Park, aka “Dolo”, is one of the most popular parks in San Francisco, especially when the sun is out, since this neighborhood is known for being one of the sunniest in the city.

On a sunny weekend, you’ll be hard pressed to find a patch of green to plant yourself on, but that’s what makes Dolores Park so much fun. Yes there is a playground for kids, and basketball and tennis courts, too. But the real sport here is people watching.

You’ll hear music booming between dog barks; people toss footballs, tightrope walk, and fling their Frisbees. Bodies slathered in oil glisten in the sun; ice cream melts down the arms of laughing children; the whiff of cut grass (and other questionable varieties) linger in the air. Vendors will also come around to sell a variety of snacks and drinks, and you’ll also encounter people collecting your cans after they’re empty.

The abundant restaurants and markets in the area (Bi-Rite and Tartine are two popular ones on 18th street, just a block from the downhill portion of the park) make make it easy to pack a picnic and fuel your day out. All you need to do is bring a blanket, plop down on a hill where the views reach to downtown, and chill out San Francisco-style.

Dolores Park is named for Miguel Hidalgo, a priest in Dolores, Mexico who urged his countrymen to overthrow their Spanish rulers in 1810, sparking Mexico’s battle for independence. A statue in his tribute stands in the center of the park.

Mexico City’s answer to the Champs-Élysées, the wide, tree-and-statuary-adorned Paseo de la Reforma was first known as the Paseo de la Emperatriz, laid out as a ceremonial lane to take Their Majesties Maximilian and Carlota between the Centro’s government palaces and the imperial residence atop Chapultepec Hill. Today, it functions as one of the city’s most striking business districts, lined with skyscraper banks, offices, apartment towers, and shopping centers, and studded with old-fashioned traffic circles that add big-city excitement. Be sure to hit the roundabout that’s home to Mexico’s Monument of Independence—a beautifully carved column crowned by a gilt, winged Victory that has come to symbolize the city. Great for strolls day or night, Reforma is especially appealing on Sundays when the boulevard is closed to motorized traffic in favor of cyclists, skaters, and just plain walkers.

A cooking school by day (Wednesdays and Sundays, to be specific), Black Sesame Kitchen hosts a 10-course family-style meal on Tuesday and Friday nights that allows visitors to sample Chinese dishes from a variety of regional cuisines. Most who arrive at Black Sesame Kitchen are strangers before the meal—but it isn’t uncommon to make friends over good food and generous pours of wine. ¥300 per person; advance bookings only.

Set in a refurbished Victorian hunting lodge on a 26,000-acre estate, Shieldaig Lodge is the epitome of Highland romance. With everything from breathtaking views of Shieldaig Bay to log fires, cozy lounges, and an extensive whisky and gin collection, the hotel offers Scottish hospitality at its finest, surrounded by stunning scenery. Quietly elegant, the 12 guest rooms come furnished with antiques and luxurious touches like Egyptian cotton sheets, goose-down duvets, and homemade shortbread from the hotel’s kitchen. For utter opulence, book the suite, which features a four-poster bed, separate sitting room, and rolltop tub with views of the bay.

At the restaurant, rare-breed lamb, Highland cattle, and deer from the hotel’s estate provide the raw ingredients for the sumptuous menu. Also available are crabs, lobster, langoustines, oysters, and scallops caught by hand right in front of the property, and vegetables grown in the on-site walled garden. After dinner, grab a nightcap in the Liberator Bar, which stocks an ever-growing collection of more than 110 gins and 250 whiskies from around the world. The next day, visit the lodge’s falconry (home to eagles, falcons, hawks, and owls), or have the concierge arrange a local activity, from deerstalking and fly-fishing to hiking, boating, and pony trekking.

Quiet, hidden beaches that once defined the Caribbean are still favored by discriminating travelers. Serene and blessed with a few basic facilities (including parking, restrooms, and changing areas, as well food trucks), Brewers Bay Beach offers visitors an easily accessed, languid, sweeping shore. It’s an ideal spot for grabbing a towel, relaxing, and watching the sun set. With shallow, calm, clear, and reef-protected waters, the beach is popular with families, who can enjoy the gentle surf. Snorkeling is also popular, and the beach is home to stingray and turtle communities. Despite its secluded feel, Brewers Bay Beach is located near the University of the Virgin Islands campus and Cyril E. King International Airport.

Why we love it: A sprawling retreat offering high design and a beachfront location

The Highlights:

• Guest rooms with private plunge pools or whirlpools
• The only Thalasso therapy wellness spa in Baja
• Five separate pools, plus 4,000 square feet of beachfront

The Review
Though the Baja Peninsula has welcomed a slew of luxury properties over the past few years, it seems the 128-room Solaz is only in competition with itself. First, there are the sophisticated stone-and-wood interiors, which balance high-tech details (remote controlled lighting) and luxe amenities (outdoor showers, private plunge pools) with locally sourced decor and wall sculptures by Mexican artist César López Negrete.

Guests even have the option to add personal butler service, which can arrange everything from swimming with whale sharks to ordering a bottle of local wine from the property’s wine cellar. Outdoors, the landscaping features endemic desert plants like agave and cacti, with a hardly a palm tree in sight.

Then there’s the spa, a 10,000-square-foot refuge that features the region’s only Thalasso therapy seawater treatments and a Himalayan salt igloo. Five pools (including two sleek infinity ones that overlook the Sea of Cortez), four dining outlets (a Mexican breakfast spot, a seafood restaurant, a poolside cafe, and a coffee lounge), a beachfront fitness center, and 4,000 square feet of white-sand shoreline complete the desert dream.

Wine aficionados set their sights on the Guanajuato Wine Route, now perhaps second only in Mexico to the trails in Baja California’s long-established Valle de Guadalupe. While wineries have existed in this region for several decades, San Miguel only recently received official designation as a wine route, thanks to wineries like Vega Manchón (owner Ricardo hails from Mexico City); Bodega Dos Búhos, where art by Peter Leventhal mesmerizes visitors almost as much as the wine; or Vinícola Toyán. Newcomer labels like Santísima Trinidad have joined the old-timers in hosting vendimia events every weekend in August, with Santísima adding extra attractions like polo games and olive-oil demonstrations. No going Sideways for oenophiles here; they will head home with a new wine destination secret—and a bottle or two.

For more than 30 years, the Post Ranch Inn, which sits along a cliff 1,200 feet above the Pacific Ocean, has been a go-to retreat for devotees who believe well-being starts with a place that honors its natural environment—and treads lightly on it, too. Big Sur architect Mickey Muennig designed the 40 guest rooms that rely on solar power; all were fashioned out of recycled wood, and the structures blend in with the Santa Lucia Mountains. Views through enormous windows face either the Pacific Ocean or the mountains. Wellness plays a role in every experience on offer, whether it’s a reflexology treatment, a shaman healing session, a doctor-led sleep program, or a private guided hike or meditation session in the nearby ancient forests.

Consistently ranked among the world’s top beaches, and easily among the most popular and visited ones in Anguilla, the white and light pink sands of Shoal Bay host a casual and social atmosphere, with a plethora of bars and eats. The bright turquoise water is what Anguillan dreams are made of; water-sports options abound, from snorkeling right off the beach to parasailing and diving. Weekends get busy, with families flocking here and music echoing along the strand, especially from Gwen’s Reggae Grill. But if you just want to rent a chair and relax for the day, you can normally find a spot of Shoal Bay to call your own.

It makes sense that the California cool of James Perse’s clothing and accessories for men and women has made its way to Cabo, where its sold at one of several shops that opened on the property of Flora Farms in late 2015. Whether you forgot to pack for the coastal climate of Baja or you just want to expand your wardrobe, attentive staff can help you add a few items to your style repertoire.