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Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.

Sure, the Hotel Vintage is classic (it was built in 1894 as the Hotel Imperial, one of Portland’s most iconic grande dames, and is listed on the National Register of Historic Places), but its name references another kind of vintage: the many renowned wines of the surrounding Willamette Valley. When the hotel reopened in 2015 after an extensive renovation, it announced partnerships with 117 local wineries (one for each guestroom), each of which sends a representative at least once a quarter to pour at the guest-only wine hour held every evening. Rooms feature original artwork made from recycled corks, and the trendy lobby bar (named for Bacchus, the god of wine) and local landmark of a restaurant offer an impressive list of some of the best local and Italian wines.

Even those who don’t share the hotel’s passion for vino will find plenty to love, from the famously superlative Kimpton service to the private outdoor hot tubs and custom Public bicycles available to borrow. Also on-site is a game room—an extension of the lobby bar where guests and in-the-know locals mingle over retro video game consoles (Atari, anyone?), shuffleboard, and pool. We’ll raise a glass to that.

Rising from the ashes of the 60’s Red Lion Hotel is the east side’s latest entry into Portland’s hip hotel scene—the Eastlund. Cut from the same pedigree as the downtown Modera Hotel, the Eastlund is a welcome upgrade in the evolving convention center area. The fun starts in the bright, expansive lobby, where eye-catching art welcomes visitors. The staff is tuned to deliver exceptional customer service, and the vibe is genuine and unpretentious. Amenities include great food, local spirits, tech-savvy rooms, and super-fast Wi-Fi throughout the property.

The rooms and public spaces put art front and center, while the meeting areas are wired for productivity. Business and leisure travelers also benefit from attention to detail and a staff committed to getting it if it’s not already available. The efficient, comfort-forward rooms boast big flat-screens and colorful décor, and the river and city views from the upper levels are spectacular day and night. An easy MAX ride from the airport, The Eastlund is also delightfully located within walking distance of a variety of transportation, entertainment, meeting, and dining opportunities. With so many on-site amenities, however, you might just find yourself pleasantly planted during your Portland stay.

Houston’s first boutique hotel, the Lancaster is also the oldest continually operating hotel in town. Built in 1926 by Sicilian-born Houston investor Michele DeGeorge, it’s now owned by Texas-based hoteliers Matthew Newton, Jay Shinn, and their respective families, all of whom work hard to maintain the hotel’s reputation for personalized service and classic style.

Extensive renovations following Hurricane Harvey brought classic Regency style to the traditionally Italiante property, from clean, elegant lines to a more-open floor plan. The hotel also added a focus on visual arts, bringing in a collection of more than 200 contemporary works by renowned Texas artists to be displayed throughout the public spaces, suites, and 93 guestrooms. Rich in Houston history, the Lancaster was named a Texas historic landmark in 1984 and is now the city’s only member of Historic Hotels of America. Rooms are comfortable and immaculate—albeit cozy quarters. And just as if you were a guest in a friend’s home, there’s complimentary Wi-Fi and a full-service American breakfast buffet with coffee, housemade scones, granola, fruits, farm-to-table eggs, bacon, and sausage. At on-site restaurant Cultivated F+B, guests can also look forward to contemporary American dishes like deviled eggs, braised short rib tacos, and cast iron–seared scallops.

First opened in 2004 in a former office building in the Central Business District, the Loews New Orleans Hotel completed a $4 million renovation in November 2014. The new look is modern, but with a nod to the Big Easy: rooms and suites (which, by the way, are among the most spacious in town) are done up in soothing blues and grays, and feature local photography on the walls, and the carpets have a wrought-iron fence motif. Large picture windows afford vistas of the city or the Mississippi River.

Run by the legendary Brennan family and named after the vivacious Adelaide Brennan, the hotel restaurant also got a makeover—think canary-yellow seats, teal tufted banquettes, and Andy Warhol–esque pop art of its namesake.

Opened in April 2015, this is one of the newest additions to New Orleans’ hotel scene. It’s also one of the most unique. Set in an 1854 warehouse near the Port of New Orleans, the property pays homage to its past as well as to its Arts District location. The look is contemporary industrial, with plenty of original architectural details (hardwood floors, exposed piping and brick, wall-to-wall windows) paired with Tivoli radios, flat-screen TVs, free Wi-Fi, and other modern conveniences. The hotel lobby is part art gallery, with a rotating collection curated by the New Orleans Center of Creative Arts, part commissary, with locally crafted products displayed in chandlery cases, and part coffee shop, with pastries from the neighboring restaurant—which is one of the hottest openings this year.

Compere Lapin (French for “brother rabbit” and also a fictional character in Caribbean and Creole folk tales) serves food that draws on chef Nina Compton’s island roots, classic French training, and traditional Creole fare. The result is wonderfully colorful dishes like conch croquettes with pickled pineapple tartare sauce, roasted jerk corn with aioli and lime, and curried goat with plantain gnocchi and cashews.

First opened in 1893 as Grunewald Hotel, this historic building stretches an entire city block and has a storied past that’s equally expansive. The Roosevelt has played host to presidents and senators, duchesses and dignitaries, actors and actresses. Huey Long kept a suite here in the 1930s and could often be found propped up at the Sazerac Bar (where his go-to cocktail was the Ramos Gin Fizz). Entertainers from Ella Fitzgerald and Frank Sinatra to Tina Turner and Ray Charles have performed in the Blue Room.

A $145 million rehab, completed in 2009, restored the hotel to its former glory. Now part of the Waldorf Astoria Collection, the property combines the grandeur of yesteryear with all the trappings of a modern luxury hotel—including a lavish Waldorf Astoria Spa and a hip Italian eatery.

At first glance the small little market open on Thursday evenings at St. Clements Parish in the Makiki neighborhood of Honolulu does not seem like much to stop for. However, I often took friends there or pointed them in that directions for a dinner where trying local food and some old favorites is as easy as visiting a couple of the food stands. The variety of food is great with Thai food, Hawaiian fare, fish tacos, pies, crepes of all flavors, and fruits and veggies to round out a healthy meal. The people are friendly, tables are set up to enjoy your food there or you can take it home for later. Either way, the Makiki market is an great option to easily grab dinner on a Thursday evening. Open Thursdays 4:30-7:30pm

Many New York hotels have style, but not all have character—the Marlton is a fine example of a property where the two are powerfully present. Originally built in 1900 as a cheap place to stay (and attracting the likes of writers including Jack Kerouac) this nine-story property was taken under the wing of hotelier Sean MacPherson (the Bowery Hotel, the Jane) and transformed into a downtown hot spot where no one seems to care that the rooms are tight on space, even according to New York standards. What square footage the rooms lack, the common spaces make up for—there’s a fire burning in the lovely lobby, complete with an espresso bar, along with a cocktail bar and French-feeling restaurant, Margaux, at the back, with a gorgeous, sunny solarium (a charming feature that has inspired many return guests). Rooms are thoughtfully designed, with inviting bathrooms. Striking the right balance between hip but not too fancy, the Marlton is a comfortable property that provides much more than just a place to sleep.

A breezy little beach hotel filled with rough wood, natural linen, and flea market finds, the Rose seems, to the uninitiated, like a pure product of quirky Venice’s hipsterfication. In fact, the historic, wood-and-stucco building was built by the beach town’s founder, Abbot Kinney, in the early days of the 20th century; rumor says it was his private brothel, frequented by such friends as Charlie Chaplin. By the 1970s, at the height of Venice’s drug culture, the building had become a flophouse of sorts, and neighbor Dennis Hopper was known to drop by. Before two British photographers discovered it, the house had turned into a mural-covered crash-pad for surfers, yogis, and beach bums of all kinds.

Looking at the low-key Rose now—the town’s first true boutique hotel, barely half a block from the beach—one would hardly know that the entire history of Venice had passed through it. The rooms are spare but stylish, with large windows, art photography, and vintage furniture. Some rooms are large enough to live in, whereas others share a hallway bathroom. Amenities are minimal—Stumptown coffee, bicycle rentals—but a relaxed beach house that attracts artists and creatives looking to delve into Venice’s eclectic, vibrant culture doesn’t need to try too hard to be cool.

An art deco icon, built in 1939 for the silver screen stars of Hollywood’s Golden Age, the Hotel Shangri-La is a beachfront beauty made for decadence. As the original Shangri-La—the big chain is just leasing the name—the boutique hotel has long been a hideaway for celebrities, a home-away-from-home for design-conscious international elite, and a host of some of Los Angeles’ most elegant soirées.

Still run by the descendants of its founder, Malcolm Mackay, this 114-year-old family-owned working cattle ranch in Roscoe, Montana, has been hosting guests—Roy Rogers and Robert Redford among them—since the 1980s. Lazy E-L Ranch is often booked a year in advance due to a capacity of just 14 guests who stay in three period cabins furnished with Western art, family pictures, and Navajo rugs. Instead of a formulaic schedule of staged chuckwagons, cowboy sing-alongs, roping practice, and nose-to-tail trail rides, guests have the option of a more authentic experience, joining ranch staff as they manage stock on 12,000 acres roamed by moose, deer, and bald eagles. The main draw here is integrating into ranch life, feeding chickens and horses, cleaning barns, and helping prepare family meals (though chores are optional). There are no guest cattle drives, but experienced riders can occasionally join or observe Lazy E-L professional cowboys moving 2,000 head of cattle. For guests preferring play to work, there’s horseback riding and hiking across pristine alpine pasture and barren plateaus; non-horse people can mountain bike down the terrifying Beartooth Highway, play soccer, baseball, and croquet, fish a private six-mile section of the West Rose Bud River, or raft the Class IV Stillwater River.

This family-owned and -managed 1,000-acre guest ranch in Lewis and Clark County is paradise for riders of all ages looking to improve technique while learning about equine psychology and Western working life. The owners, Zack and Patty Wirth, and two of their six children, all direct descendants of 1860s Montana homesteaders, breed and train quarter horses and hold wide-ranging riding rights on a neighboring ranch of 85,000 acres. Guests, a maximum 20 at a time, ride according to their interest and level; time in the saddle (or bareback) might be spent in the ring, on scenic trail rides, endurance training, or learning to rope and work with the Wirths’ 30 Corientti and Longhorn cattle.

Four cozy rooms of the same size but with different bed configurations have fireplaces and mountain views. The atmosphere is communal and convivial, the hosts dining with guests and taking note of the weather and individual interests to plan activities. Many teen visitors fulfill dreams of unlimited horse time; for non-riding family members or partners there is guided shooting, hiking, and mountain biking. There’s also technical fly-fishing on the Little Prickly Pear Creek, a spawning ground for rainbow and brown trout. For rock hounds, fossil-rich shale cliffs sit just a mile away from the barn and guest rooms.

Peggy Dulany, a New York philanthropist and daughter of David Rockefeller, bought J Bar L to protect the 620-square-mile Centennial Valley, a former Native American hunting ground settled by a few cattle-ranching families in the late 19th century—and which still has no towns, let alone paved roads, gas stations, shops, or subdivisions. To conserve the rangeland way of life, she hired locals to run a holistic grass-fed cattle business on the principles of rotational grazing and natural stockmanship. To share the landscape with nature-loving travelers and to keep the valley looking as it was, Dulany restored several abandoned 19th- and early 20th-century homesteads. These self-contained vacation rental homes range from a Sears Roebuck family house, now solar-powered, to isolated cabins on a bend of the Red Rock River. All come with fully-equipped kitchens and are tastefully filled with Western-themed furnishings and antiques; some have outdoor hot tubs.

J Bar L no longer offers working weeks for would-be cowboys but will match guests with geologists as well as with hiking, bird-watching, and fly-fishing guides. Horse lovers can hire ranch mounts for guided daily rides on rangeland that is home to pronghorn, elk, and Black Angus cattle, or up the slopes of the 10,000-foot Gravelly Mountains where wolves, grizzly bears, and bald eagles roam.

There are helipads but no cell phones or young children at Triple Creek Ranch, a 600-acre luxury Western playground on a slope of 10,157-foot Trapper Peak, Montana’s highest mountain, near the Idaho border. Owned by Craig and Barbara Barrett (he, the former CEO of Intel; she, a former astronaut and U.S. ambassador to Finland), this elegant, high-end dude ranch offers sapphire pan mining, scenic trail rides, fishing from stocked trout ponds, and guided hiking, cross-country skiing, and snowshoeing (including starlit expeditions), as well as themed weekend stays focusing on art, food, and wine. The owners’ no-hunting policy has resulted in large herds of elk and other game gravitating to the property, and guests frequently spot animals from huge log cabins decorated with leather furniture and original Western-themed art and equipped with wood-burning fireplaces, private decks, bar, Blu-ray players, and working Wi-Fi connections. (Though the ranch deliberately has no cell phone signal.) From May through October, for additional fees, the ranch pairs up guests with professional rodeo trainers and Orvis-endorsed fly-fishing operators. In winter, the lodge facilitates transportation, tickets, and equipment rental vouchers for the nearby Lost Trail Powder Mountain downhill ski center (300 inches of snow annually) and Chief Joseph Cross Country Ski Area.