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An ancient atoll, Molokini lies 2.5 miles off Maui’s south coast, where the water is calm, clear, and teeming with marine life. Here, snorkelers and scuba divers can expect up to 150 feet of visibility, allowing for perfect views of yellow tang, parrot fish, black triggerfish, bluefin trevally, and even moray eels. To explore it for yourself, book a tour with Maui Classic Charters, which sails to Molokini in a 55-foot catamaran with a glass-bottomed viewing room. Choose one of the early-morning trips for a better chance of calm seas and bigger sea creatures like octopus and eagle rays, and bring along snacks, sunscreen, and, for those who run cold, perhaps a rash guard or thin wet suit, especially in the winter months.

Built in a former auto garage in Nashville’s Gulch neighborhood, this five-room boutique hotel replaces industrial vibes with low-key sophistication: The whitewashed rooms—some with loft-style living spaces—feature high ceilings, custom furniture, and high-end amenities like Sferra linens and Turkish cotton robes, and the subway-tiled baths gleam with vintage taps.

There is no front desk, but guests receive a passcode for the entry keypad before arrival, and a concierge service is always on call. Have some down time? A comfortable sitting area is set up with board games and a large sideboard stocked with complimentary refreshments and coffee throughout the day, which makes the 404 the perfect spot for urban explorers who like to come and go as they please. But don’t miss dinner at the 404 Kitchen. Housed in a shipping container and accessed through another keycode doorway, it’s one of the city’s top restaurants.

If you happen to be in town for Cherry Creek’s annual arts festival in July, Halcyon makes a great base for exploring the neighborhood’s shops and galleries. Crisp white guest rooms with masculine touches have Nespresso machines, smart TVs, and sculptural turntables, as well as subway-tiled bathrooms with brass fittings and peekaboo showers; upgrade to a terrace room for a private outdoor space in which to bask in the Colorado sun. In keeping with its surroundings, the hotel displays more than 700 works by local artists, with an original piece in each room, but there’s plenty of reason to linger in the public spaces. A rooftop pool is lined with neutral-hued cabanas and white cushioned chaises, and two restaurants satisfy every kind of craving: Departure Restaurant + Lounge’s Asian-fusion menu covers miso ramen and roasted-duck fried rice, while Quality Italian offers shareable lasagna, dry-aged steaks, and cannoli prepared tableside. Just don’t be put off by the $30 per day amenity fee on your bill. Though it includes standards like WiFi and pool and fitness-center entry, it also gets you snacks and drinks at the Kitchen Counter, plus access to a Range Rover shuttle for stops around the neighborhood and the Gear Garage, which lends out everything from snowshoes and a Piaggio scooter to Leica and Go Pro cameras during your stay.

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.

A stay at this resort offers the best of many worlds: easy access to San Antonio and its airport, proximity to scenic Hill Country and its wineries, and plenty of on-site amenities to encourage you to hang around. Spread over 600 acres, the property includes an 18-hole golf course, a nine-acre water park (with a winding lazy river and 650-foot rapid river ride), hiking trails, and a 30-room spa, where treatments incorporate Texas-grown ingredients like lavender and sassafras. The facilities fan out from the LEED-certified main building, which houses 1,000 warm, comfortable guestrooms, many of which look out onto the main pool. There are also enough restaurants to warrant a multi-day stay, from an organic-focused spa bistro and a sports bar with local brews, to a Texas-inspired main restaurant and a fine-dining steakhouse set among the golf greens. Each spot uses ingredients sourced within a 150-mile radius of the hotel, and aims to highlight Texas wine and beer. While the kids are off enjoying the water park or video game arcade, adults can take a tequila tasting class or settle into a rocking chair with a good book—then everyone can meet around the indoor or outdoor fireplaces to trade stories.

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.

If your dream vacation involves the ultimate in luxury, the St. Regis should be at the top of your list. The 151 rooms feature hand-crafted chandeliers, original artwork, and macassar ebony furnishings, as well as Italian marble bathrooms that have soaking tubs and TVs hidden in the mirror. But the real draw is the service: All guests have access to the butler desk, which can fulfill requests both big and small, from unpacking your suitcase to delivering the morning newspaper, and designated pool chamberlains mist guests with Evian and deliver frozen-fruit skewers and coconut water at the 40,000-square-foot Pool Piazza, complete with red-striped chaises and waterside bar. While the promise of massages in the Remède Spa and afternoon tea in the English-style Astor Court make it hard to leave the resort-like premises, the hotel’s location a five-minute walk from the Buckhead shopping complex may sway you. And if you need help hauling your spoils to your room, remember there’s a butler waiting just around the corner.

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

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.

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.

Seeing wild wolves in Yellowstone National Park is nearly impossible without a guide; amateur wolf watchers in any case need high-powered binoculars and tolerance for cold, as the best observation season is winter, when wolf fur stands out against the snow. But at Howlers Inn Bed & Breakfast & Wolf Sanctuary, just outside Bozeman, guests year-round can observe a captive-bred pack from their bedroom window, and even pet a wolf through the chain-link fence of the inn’s four-acre sanctuary. Owners Chris and Mary Martha Bahn originally opened the federally licensed shelter in 1993 for a single rescued wolf that was unable to return to the wild. Built to fund the shelter as it accommodated more animals to live as a pack, the cozy log B&B sits on 42 acres in Bridger Canyon amid boulder-strewn meadows backed by pine-covered hills. Two wolf enclosures, with a seasonal pond and creek, are currently home to five spayed or neutered timber and Alaskan tundra wolves, born in captivity, whose owners could no longer keep them. The Bahns do not breed or exhibit the animals for profit, but they’re happy to discuss wolf conservation as well as the controversial issues of game farm breeding and hunting. Guests are welcome to photograph the human-habituated animals during their stay.

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.

This chalet-style lodge takes its name from legendary Norwegian skier Stein Eriksen, the 1952 Olympic giant slalom gold medalist and 1954 World Cup champion. When he agreed to help develop this ski-in, ski-out spot in the 1980s, he drew from his experiences at the best ski hotels in Europe, lending the lodge an Alpine feel. Inside, fireplaces, stone walls, and rich wood ceilings complement the mountain surroundings. Guestrooms are equally thought out, with beamed cathedral ceilings, stone fireplaces, and leather furnishings. Select rooms have jetted tubs and heated floors.