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The Hole is a geologic formation that offers a dramatic look at the same karst process that created Conch Bar Caves and other limestone sinkholes and caverns found throughout the Turks and Caicos Islands. As its name implies, the Hole is area’s largest limestone sinkhole, about 60 feet deep and 50 feet across. A pool of water at the bottom connects to Juba Sound’s nearby ponds through an underground tunnel. You can rent a car and drive to the Hole on the east side of Juba Sound; however, use caution when walking near the edge, as limestone can crumble.

St. Kitts’ water taxis—basically anyone with a boat willing to make the crossing to Nevis—will drop you right on this beautiful stretch of sand, making Oualie Beach the perfect day trip. Once on land, head to the Oualie Beach Resort, where you can hang with guests and locals at the on-site restaurant and bar. If you’re feeling adventurous, ask the bartender for a sample of one of the house-infused rums, made with a variety of local plants and herbs. Afterward, walk down to the beach, where you’ll find watersport vendors and even a small spa for some additional relaxation.

The second location of the Sydell Group’s New York flagship, NoMad Los Angeles embraces its past as the Bank of Italy—imposing columns and all. In the lobby of the landmarked building, much of the original Neoclassical style, such as the Doric columns, coffered ceiling, and marble floors, was preserved, complemented by the addition of floral textiles in rich jewel tones. Even the original vault, which once housed 12,000 safety deposit boxes, and its 50-ton door were kept intact. The color palette across the 241 lavish rooms draws from the exquisitely maintained gold-and-blue Italianate lobby ceiling, with custom furniture, original artwork from design studio be-poles, and freestanding bathtubs in most rooms adding to the luxurious feel. Details like nightly turndown service, marble bathrooms, and custom linens by Bellino mean a five-star stay is all but guaranteed.

With its historic pueblo-inspired architecture and Spanish Revival style, this landmark Santa Fe hotel looks like it dates back much earlier than 1922, when it was designed by two of the area’s top architects: Mary Elizabeth Jane Coulter and John Gaw Meem. And, in fact, despite the imposing building’s relative youth, the legacy of La Fonda dates back to the 1600s. An inn or hotel has stood on this site since the city’s founding at the end of the Santa Fe Trail.

Now, as one of the city’s most iconic luxury hotels, it presides over the historic Plaza and boasts some of the best views of the city and surrounding mountains and desert. Thanks to a complete (and completely faithful) renovation in 2013, rooms are now bright and airy, outfitted with handcrafted furnishings, local artwork and textiles, energy-efficient casement windows, and all the luxuries expected of a modern grande dame. The fine-dining courtyard restaurant is one of the most romantic dining destinations in town—trumped only by the rooftop Bell Tower Bar, whose sunset views and margarita menu draw locals and in-the-know visitors alike. Throw in a heated outdoor pool (open year-round, a rarity in Santa Fe) and a decadent spa, and it’s no wonder that La Fonda has maintained its reputation for superlative hospitality for so long.

Fans of the Montage brand’s Laguna Beach and Beverly Hills flagships will love this mountain version, a ski-in, ski-out hotel wedged into the head of Empire Canyon. The sprawling, Craftsman-style manor debuted in 2010, solidifying Deer Valley’s standing as one of North America’s most luxurious ski resorts. Service shines, starting with the “Mountain Host,” who greets guests in the majestic lobby rotunda. Up the grand staircase, the full-service Vista Lounge acts as a communal living room, with vaulted ceilings, exposed wood beams, floor-to-ceiling windows, and leather furnishings gathered around limestone fireplaces. To further entertain guests, there’s also a museum-quality collection of Western art, including Carl Runguis panoramas, John James Audubon prints, and Frederic Remington portraits.

The hotel’s X-shaped footprint means nearly every room has small deck with mountain or valley views. Averaging around 600 square feet, large guestrooms are airy and inviting with lofted ceilings and soothing natural hues. Remote-controlled gas fireplaces are the centerpiece of each room, though the bath suite with heated limestone floors, marble vanity, rain shower, and soaking tub could occupy your entire evening.

Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.

The Eastern Market, now a National Historic Landmark, opened in 1873 to serve the Capitol Hill neighborhood (an 1805 version, located down by the Navy Yard, was a casualty of the War of 1812). The brick market hall, packed with butchers, bakers, vegetable markets, cheese vendors, flower kiosks, and a lunch counter, is bright and charming. Under the shed roof outside, additional local produce is displayed and sold. On weekends, booths selling vintage goods and handmade jewelry, housewares, and clothing do a brisk business down the center of 7th Street. Crowds spill out of the cafés, taco joints, and bagel shops occupying the first floors of the row houses along the block, adding to the lively mix at the market.

One of the most popular anchorages in the BVI, Cane Garden Bay is home to a lively boating community. It makes a great day trip, whether you arrive by land or by sea. In this scenic cove, calm blue water laps a gentle arc of blinding white sand. Open-air beach bars offer lounge chairs and rum drinks; a few shops sell souvenirs, along with provisions for the sailors coming in off their boats to stock up.

Cruising through Prince Christian Sound, passengers only see one sign of human habitation against the stark landscape: the tiny Inuit village called Aappilattoq, which means “sea anemone” in the local Greenlandic Inuit language. Aappilattoq sits perched at the edge of the water with towering mountains all around, making the village virtually inaccessible by land. The cluster of colorful houses is home to around 100 people, rugged individuals who mostly fish and hunt the harsh terrain as they live isolated from the outside world (except for the occasional arrival of a boat or helicopter).

The Coronado Bridge links San Diego to Coronado Island—and the present to the past. In the span of just 2.12 miles, you’ll travel from the digital age to a century when “electrified” hotels were practically unheard of. When the Hotel Del Coronado debuted in 1888, its electric lights and telephones made a sensation—as did its resplendence. In 1892, a young guest named Noel proclaimed in a letter to her family back east that “the red and the white between the bluest sky and the bluest water is like a beautiful dream in a fairy story.” Legions of A-listers have checked in ever since, as a who’s who of vintage portraits attests. But while a stay here is delightfully nostalgic—featuring bike rentals, beachside cabanas, and evening clambakes—the 757-room hotel doesn’t live entirely in the past. Take advantage of its upscale spa, spin classes on the beach, and restaurants serving updated takes on coastal cuisine along with creative cocktails. In the historic Victorian Building Suites, you’ll find modern coastal-chic interiors, streaming TVs, and, of course, Wi-Fi. The Beach Village Suites include additional modern luxuries—like a Sub-Zero fridge and dedicated concierge to help you fill it.

Just outside Capitol Reef National Park, Cafe Diablo serves Southwestern fare with a local twist. From pumpkin-seed-crusted trout to rattlesnake cakes with ancho-rosemary aioli, the dishes are classics in an unexpected way. Casual and family-friendly, the restaurant offers a taste of big-city dining in a low-key atmosphere. Ask the knowledgeable staff to recommend the perfect wine or beer for your meal, or choose something from the extensive selection of tequilas.

Set on 4,200 secluded acres of hillocks, ponds, and gardens at the foot of the Tennessee Smoky Mountains, this award-winning resort, a member of the prestigious Relais & Châteaux brand, is awash in genteel luxury, from its splendid spa to its exquisitely appointed rooms, suites, and cottages. But make no mistake, the family-owned property takes the “farm” in its name to heart: Its James Beard Award–winning restaurant, The Barn, as well as the more informal Dogwood restaurant, were early leaders in the farm-to-table movement, welcoming guests who come to pay homage to the inn’s self-described foothills cuisine.

In addition to several gardeners, the farm employs its own butcher, cheese maker, and beekeeper, along with a preservationist who makes pickles, jams, and jellies. The staff raise their own sheep, pigs, and chickens, and forage the land for mushrooms, berries, ramps, wild crab apples, and muscadines—which you’ll share at the table with other guests (all meals are included in your stay). Thankfully, a roster of on-site activities—including cycling, wakeboarding, archery, paddleboarding, hiking, fly-fishing, swimming, tennis, and golf—allow you to indulge without feeling guilty.

Italy’s beloved region of Tuscany brings to mind bucolic vineyards, rolling hills, and roads lined with towering cypress trees. But there’s plenty else to delight and even surprise travelers. Consider the quaint town of Punta Ala: located along the southern Tuscan coast, it’s under the radar of most travelers, yet the go-to summer escape of generations of Romans and Florentines.

Punta Ala strikes a balance between relaxation and understated elegance that encourages lingering, and the same goes for its premier place to stay: Baglioni Hotel Cala del Porto. Set against the backdrop of the Mediterranean Sea and with two adjacent beach clubs (La Vela and Alleluja), the hotel’s 38 airy rooms offer views of the gardens and marina. In the heart of Maremma, Hotel Cala del Porto is perfectly located for day boating trips out to the island of Elba, wine tasting at notable Tuscan wineries, and some of the best golfing in Italy. The regional park Bandite di Scarlino beckons with hiking trails ideal for early morning risers.

Brandywine is just one of half-a-dozen provincial parks that surround the Sea to Sky Highway like a fir wrap. A trailhead located just 12 miles south of Whistler leads to a 15-minute walk through the mixed hemlock forest to a 200-foot cascade. The falls overview is merely a picturesque appetizer for the fantastic wilderness beyond. The Lava Lake trail provides a marvelous meander through the forest, and if it’s a hot day, you might want to hike all the way to Swim Lake. You can also access the Sea to Sky Trail and head north to the Whistler Train Wreck then hike to the Valley Trail through Whistler and beyond. The park tripled in size in 2010 to fully enclose the habitat of the endangered red-legged frog, so keep an eye peeled for peepers.

There’s a lot of tourists Instagram-browsing in Kyoto’s famed Nishiki Market shops, which hawk salt-pickled cherry blossoms, barrels of other pickled vegetables, and takoyaki (fried octopus balls). But step off the bustling main drag and into this legendary knife shop to discover a rarefied world of chefs deliberating over blue steel boning knives with magnolia handles, or 12-inch Japanese alloy with rosewood and water buffalo horn. The tiny shop is chockful of handmade blades and cutting utensils gleaming like evidence behind glass cases. But Aritsugu is principally known for its custom-made knives, especially popular with lefties. The shop will also engrave your name or initials on your blade for free via the revolving whetstone behind the counter.