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The San Francisco Proper Hotel is the hottest new hotel in town. The reason why? International grande dame of maximalism, designer Kelly Wearstler, revamped a down-and-out tourist hotel deep in the heart of the city, and established the Proper as a magnet for trendsetting visitors and locals. When guests arrive at the 131-room hotel and step inside the flatiron building, they’re treated to Wearstler’s signature pattern-on-pattern aesthetic. In the ground floor lobby, Wearstler sets the mood with salon-style seating areas using richly reupholstered vintage furnishings and Cubism-inspired paintings. Michael Adams, formerly of Central Kitchen, oversees the hotel’s main restaurant, Villon. And while the Proper isn’t the place for those looking for a Zen retreat, it is the place to order a Fifi the Flea cocktail (Tequila Ocho Plata, Ancho Reyes, Ancho Reyes Verde, grapefruit, honey, vanilla, lime, smoked salt) at Charmaine’s, the stylish rooftop bar. Between the fire pits and the bird’s-eye view of Market Street all the way to the bay, it’s no wonder the Proper has become the destination to see and be seen.

About half an hour south of Cancún stands the rickety wooden entrance sign to La Ruta de los Cenotes, a small highway leading into the jungle, populated only by the occasional souvenir stand or rental cabins. But the real attraction here is the cenotes: natural springs connected to the Yucatán Peninsula’s extraordinary underground river system. Ideal for swimming and snorkeling, the pools often feature diving cliffs, picnic grills, and maybe even a small zip line. Most forbid sunscreen and bug repellant to protect the water’s pristine quality. Top options include Las Mojarras, Verde Lucero, Boca del Puma, and Siete Bocas.

Starting in 2014, this collection of historic buildings was reinvented as a gastronomic hub—helping to revitalize the city’s downtown in the process. An early 20th-century citrus packing warehouse became the Anaheim Packing House, a virtual United Nations of food: Walking through the 42,000-square-foot hall, you’ll find citrusy ceviche at Urbana, fried chicken sandwiches at Sweetbird, garden-fresh hot pot at Rolling Boil, organic curry at ADYA, and matcha shaved snow at I Am. Craft beer—quickly becoming a signature of Southern California—is in no short supply, thanks to bars like Anaheim Brewery, housed inside a 1925 mission revival building. A circa 1917 marmalade factory became the MAKE Building, where you can linger over a flight of California reds at Pali Wine Co. or a plate of pulled pork at Jav’s Barbecue. The compact district is distinctly Californian, from the succulents and air plants inside to the palm trees and olive groves of Farmers Park outside—a grassy knoll where, at any given time, you might happen upon a free yoga class, a gardening demo, or a live acoustic band playing under the sun.

It’s not that vegetarians aren’t welcome at Costa Mesa restaurant Vaca. It’s that they may not feel the same unbridled excitement as those who enjoy expertly prepared meat and seafood. The innovative lunch and dinner hot spot owned by former Top Chef contestant Amar Santana celebrates Spanish cuisine, from Andalusia, Seville, Madrid, Barcelona, and the Basque region to be precise. The call at lunch is the $28 three-course prix fixe, which changes weekly. Dinner brings an almost paralyzing array of decisions: unparalleled dry-aged rib eye (the restaurant’s name, after all, is Spanish for “cow”), seafood paella, or a collection of tapas such as sea urchin with scrambled eggs, served in the spiky shell with caviar. To accompany it, pick from one of the three drinks on tap: a house vermouth, a red sangria, or a signature gin cocktail named after the restaurant. Tucked between the Segerstrom Center for the Arts and the South Coast Plaza, the restaurant is great for preshow dinner or post–shopping spree lunch. Pro tip: If you’re with a group, request a circular booth; if you’re a pair, go for the heated patio or the bar.

Tucked away on Third Street since 1979, Michael’s is arguably the best-kept secret in Santa Monica—a Cheers-like stalwart for locals, who return to proprietor Michael McCarty’s inviting restaurant and bar regularly. It hasn’t hurt that star chefs Jonathan Waxman, Nancy Silverton, Sang Yoon, and Mark Peel have all done time in the kitchen. Artwork by John Baldessari, Ed Ruscha, and Cy Twombly set the backdrop for equally creative, flavor-packed masterpieces by the current chef Miles Thompson. Modern California-sourced dishes change seasonally, but octopus is a must-order. (If you’re lucky, Thompson will be serving his confit version with burnt butter and Sichuan peppercorn marshmallow.) A relaxed, jungle-like garden patio invites late-night lingering over a drink from the creative cocktail menu; be sure to try the popular Road to Kyushu, a mix of Japanese whiskey, kumquats, cloves, and barrel-aged bitters. Pro tip: For early birds, Michael’s lounge has probably the best happy hour in L.A.: a $1.79 cocktail from 5:30 to 6 p.m. (to honor its opening year), plus the signature barbecue aioli–topped Smash Burger available in limited numbers until 7 p.m.

No matter what kind of getaway you have in mind, you can find a guestroom to fit at Castle Hill Inn. Rooms in the main house vary in size and décor, but each is kitted out for romance with a fireplace, a king-sized bed, oversized tubs, and windows looking over the water and expanses of lawn. The Turret Suite, a bi-level space, has a bedroom on the first level; on the top floor, a soaking tub on a raised floor takes advantage of the 320° wrap-around windows. Below the main house, the Harbor House’s modern guestrooms feature front-porch views of Newport Bridge and the hotel’s Grace Kelly Beach. At the far end of the 40-acre property, the Beach Cottages and Beach Houses are set along the private beach, offering views that take in both the mansions along Ocean Drive and the wild Atlantic itself. The cottages, slightly smaller and closer to the beach, have peaked ceilings with rafters. The airy Beach Houses, compactly outfitted with galley kitchens, sunny decks, ceiling fans, fireplaces, and curated shelves of books, cast a kind of never-leave spell.

One of the few hotels on picture-perfect Grace Bay Beach that can work for both honeymooners and families, Seven Stars sits on 22 acres of lush grounds at the edge of Princess Alexandria National Park and has studio to four-bedroom plantation style suites available. All feel very private. Besides wraparound terraces with awesome ocean views, the rooms here all feature full kitchens, making it easy to cook your own lunch or make snacks for the kids. That said, the house restaurant, aptly named Seven, is very good, so plan on dining here at least a few times. The spa is also excellent - perfect for honeymooners - and there is a dedicated activities concierge that will arrange all sorts of water sports and even a kids’ camp.

This gem right off Bourbon Street is close to the action but far enough (and insulated enough) to make you feel like you can get away from the frenetic pace of the city’s most famous avenue at a moment’s notice. Guest rooms are well-appointed and comfy, with plantation-shuttered windows, plush beds and sleek bathrooms. Plus, every guest gets a voucher for a welcome drink in the hotel’s smoke-free bar, the Bourbon O. Be sure to catch live music there on Friday nights, as well as bartender Cheryl Charming, whom a local magazine named Mixologist of the Year in 2014. Back at the hotel, the Roux on Orleans restaurant can satisfy breakfast, lunch and dinner desires, and a heated saltwater pool makes lazing about in a lounge chair all day very, very easy. But if you want to be the ultimage envy of Bourbon Street revelers, make sure to reserve a balcony suite; it features a porch overlooking all the boozy revelry below and lets you party above the action.

Willis Tower—originally known as the Sears Tower—was the world’s tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its “bundled tube” design by architectural firm Skidmore, Owings & Merrill was originally inspired by a handful of cigarettes and the innovative bundling changed the construction of supertall, wind-resistant buildings thereafter. The tower’s height is even more thrilling when measured from the 103rd-floor windows of the Skydeck observatory and the Ledge, a glass-enclosed box which juts more than four feet out from the side of the building so that visitors can (gingerly) walk out and stand 1,353 feet above the street.

In 1989, Chilean winemakers Augustin and Valeria Huneeus happened upon a 280-acre parcel of land in the heart of Rutherford that had never been planted with vines. The couple jumped and bought it. The result is Quintessa, one of the most spectacular estates in the Napa Valley. Today there are three different ways to experience Quintessa—all visits are privately hosted and tailored specifically for each guest. The Estate Tasting includes a walk to a scenic viewpoint, followed by a seated sampling session in the main winery building. The “Quintessential Quintessa” includes a scenic drive to a private tasting pavilion atop Dragon’s Hill, which offers unrivaled vistas of the entire valley and revolves around narratives about the property, the terroir, and how winemaker Rebekah Wineburg plies her craft. Finally, the third—and most exclusive—option, dubbed the “Collectors Experience,” offers at least three wines from the Huneeus family cellar, poured alongside the most current release. Time the visit right and Augustin Huneeus himself might come out in his signature cowboy hat to say hello and regale your group with stories of his life in South America before he emigrated to the United States.

Since 1983, food lovers in the know have headed to Santa Barbara’s renowned Paradise Café. Housed in an early 20th-century brick and stucco building with a relaxed atmosphere, the café’s oak wood grill is fueled by Santa Maria live oak—also known as California live oak—a wood that’s essential for the area’s regional style of barbecue. The flavors brought out by the oak in steaks, pork chops, roast chicken, shrimp and sausage, ahi tuna, rainbow trout, and salmon keep added seasonings to a minimum, so fresh ingredients remain the focus of the menu. The crowd favorite, the half-pound signature Paradise Burger, is grilled over oak, topped with Tillamook cheddar cheese, and placed on an onion roll—and best enjoyed with a glass of Paradise syrah, sourced from local vineyards. If you sit on the patio, give the historic mural more than a glance. It features Leo Carrillo, an old-Hollywood actor best known for his role as Pancho in the television series The Cisco Kid; he is locally beloved for his involvement in preserving and conserving California open spaces.

Two Florentine brothers were inspired by the history of radio communication to name their cushy bar Mayday—and outfit it with vintage radios (set on the tables and hanging from the ceiling), black-and-white photographs, and tons of other vintage memorabilia. The drinks, too, feel of another time, with their focus on handcrafted preparations, small-batch liquors, and organic and locally grown ingredients. Sample everything from unfiltered brews made from Tuscan barley and wheat, to a rare Scottish whisky or a green tea–infused cocktail. The atmosphere is one of collaboration: There are nightly lively music performances, the walls are lined with art installations and exhibits, and patrons are encouraged to leave their own vintage mementos. Classes in mixology and infusion-making are also available, and are a fun way to hone your skills while mingling with locals.

A clifftop eco-hotel surrounded by 50 barely touched acres on the bucolic North Kohala coast, Hawaii Island Retreat feels as far away as it gets. There are no TVs in the guest rooms, no air-con, and Wi-Fi only in certain spots. Solar and wind power provide all the electricity, while much of the fruit and vegetables are grown right on the property. Resident goats and bees supply the cheese and honey. The inn has 20 simply-furnished bedrooms in the main house, overlooking groves of cedar and pine trees, plus seven yurts a stone’s throw away, so it’s possible—likely even—that a guest might spend days here and rarely see another soul. The owners, a local spa therapist and natural healer and her physician husband, opened the property in 2009 with the express purpose of creating a wellness-focused retreat, which is why guests can sign up for classes in yoga, tai chi, and meditation, as well as facials and massages. Outdoor massage tables, placed under a tent, overlook a deep green valley. There’s also a mediation rock. So health-minded is this little retreat that it’s become a popular spot for guests recovering from serious illness or simply in search of a detox. Various packages have a wellness or spiritual theme.

After a couple of days in Mexico City, once you’re well-rested and adjusted to the altitude, why not try a little street eating? After all, some locals do it every day, and the techniques vendors use have been in place for centuries, if not millennia. A good jumping-off point is the sometimes-grilled sandwich known as a torta. The ingredient combinations are endless, ranging from egg, shredded chicken, and pork loin to the Mexican piece of breaded beef known as a milanesa—and the list goes on. String cheese and chipotles or pickled jalapeños add a lot of flavor, but do it your way. A lot of customers at a stall is good sign both in terms of taste and cleanliness. With a torta under your belt, start thinking about tacos. Or that spot with the caldo de pollo chicken soup, perfect for all kinds of add-ins. Soon enough you’re a seasoned streeter.

Unexpected surprises abound in Amsterdam. On the city’s east side, you’ll find one denoted by a tall windmill: Brouwerij ‘t IJ (the IJ Brewery), a small brewery and pub situated in the former Funen bathhouse, next to the De Gooyer windmill. Opened in1985 by former musician Kaspar Peterson, Brouweij ‘t Ij prides itself on a large selection of unfiltered, non-pasteurized beers and seasonal offerings. All are certified organic and made on the premises. Belly up to the bar next to the big mill and order your beer from a chilled tank. Follow the scent of hops onto the large outdoor terrace, where you can enjoy your brew with an order of peanuts, boiled eggs, abbey-made cheese, salami, ossenworst from Slagerij de Wit or Skeapsrond cheese from Dikhoeve Farm. The adjacent pub serves more substantial meals, as well as drinks and snacks. In addition to beer, Brouwerij ‘t Ij’s menu includes wine and non-alcoholic beverages. Guided tours are offered on weekends.