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One of the world’s most epic drives, the Hana Highway connects Kahului with Hana in eastern Maui. The scenic stretch is just 64 miles long but can take up to three hours to drive, thanks to 62 twists in the road as it winds through rain forests and past waterfalls, natural pools, and seascapes. Plan at least a half day to properly experience the drive, or slow it way down and spend a night in Hana so you can linger at places like Twin Falls, the Keanae Peninsula, the Garden of Eden arboretum, and the black sand beach at Waianapanapa State Park. Sun worshippers should also budget plenty of time for stops at Hamoa Beach and Ho’okipa Beach Park Beach Park.

Rising from the corner of Park City’s Main and Heber streets, the six-story, 33-suite Main & SKY blends a modern loft vibe with traditional ski-lodge service. Concrete, steel, and glass define the building and interior design, from the fireplace in the lobby to the elevator whisking beautiful people to their rooms. The hotel’s state-of-the-art lofts are unique to Park City, and the one-, two-, and three-bedroom suites feature floor-to-ceiling windows, full kitchens, living rooms with fireplaces and private decks with hot tubs. Sliding wall panels open to the master bathroom, the centerpiece of which is a soaking tub filled by a ceiling-mounted faucet.

Esperanza is located on the southern side of Vieques island with a laid-back vibe reminiscent of Key West. This small town has an main street that runs parallel to the ocean called “El Malecón” that is dotted with friendly guest houses, funky bars and even gourmet restaurants. It makes a great base for exploring the island’s treasures: it’s walking distance to Playa Esperanza and Sun Bay and only a 10-20 minute drive to the secluded beaches in the wildlife refuge.

This Neoclassical building from the mid-19th century stands at one end of a large urban park. The interior of the Capitol is worth a visit—its rotunda and historic rooms reflect the history of lawmaking and governing in this state. The small exhibits from every California county highlight the natural beauty and local specialties from all parts of the state. They line the downstairs addition, which is enhanced with Art Deco details and includes the governor’s office. Outside the Capitol is Capitol Park, one of my favorite outdoor spaces in Sacramento. The paths wind past trees from all over the world (a map is available), memorials, a succulent garden, and a rose garden at the other end of the park.

Located in downtown Santa Fe, this perfectly sized museum is dedicated to the artistic life of Georgia O’Keeffe (1887–1986) and houses the single largest collection of the artist’s work in the world. Rotating exhibits often include O’Keeffe’s iconic desert landscape paintings alongside lesser-known gems painted in Lake George and Hawaii (where she was commissioned by the Dole pineapple company). Often, notable pieces from established peers and contemporaries like Ansel Adams, Jackson Pollock, and Andy Warhol join hers on the walls.

“Straight ahead for 42 Miles” said the automated, slightly pitchy, woman’s voice. My road trip buddy and I looked at each other as if to check what we’d just heard. Sure enough though, the GPS was right. Straight as a die, but much, much more interesting with stops on the way to check out a coyote crossing the road, a sign marking a public phone that wasn’t there, and the remnants of some poor animal carcass that didn’t quite beat the vehicles before us.

Restaurateur Brooks Reitz built his name with this chicken-and-oyster joint that feels old-school despite its carefully crafted ambiance. On a first visit, it’s sinful not to order the perfectly salted, crispy/juicy fried chicken amalgam shellacked with a glaze of Old Bay and cayenne suspended in melted lard. That necessitates a second visit to gorge on the poached char-grilled lobster and sausage, or the Leon’s Fish Fry, a platter of shrimp, oysters and catfish. Leon’s was the first to open way-Upper King, now the restaurant hotbed, and it’s held onto its cool status thanks to its thoughtful buildout in a restored auto body shop, retaining the exposed rafters and a rollup garage door that opens to a patio out front.

No trip to D.C. is complete without ordering the district’s signature dish, the half-smoke. And while many restaurants serve it, there’s only one worthy of your order: Ben’s Chili Bowl. The popular landmark diner has been feeding the community and cultural icons since the area’s “Black Broadway” days, when jazz greats such as Miles Davis enjoyed this comfort food classic. When riots broke out after Martin Luther King’s assassination in 1968, Ben’s remained open and served both police and protesters. While the U Street Corridor has undergone an urban makeover, Ben’s has remained the same, serving its quarter-pound of half-pork/half-beef smoked sausage on a bun with mustard and onions, all smothered in spicy homemade chili sauce. The prestigious James Beard Foundation even took notice, deeming it one of “America’s Classics.” Bring cash and come hungry.

One of Playa’s newest hotels, Cacao is being touted as a “kicked-back, relaxed ‘hippie chic’ boutique, 60-room hotel. Conveniently situated on Playa del Carmen’s 5th Ave. in the heart of the destination’s fashionable restaurant, club and boutique scene it is also walking distance to the beach. Spacious, modern rooms and suites provide comfortable amenities, including bathroom toiletries by Italian fashion designer Missoni and distinctive touches by architect Rodrigo de la Peña. Dramatic architectural elements such as huge canvas accents in geometric shapes and a central court with a hyacinth lily pond combine with clean interior design and contemporary, bold color accents. The roof-top bar boasts innovative “coctelería” (mixology) experiences, along with spectacular views of the Caribbean and Cozumel Island as a scenic backdrop. Onsite Nibs Restaurant dishes up gourmet food in a serene setting, while a rooftop pool provides a refreshing escape

Situated at the base of the Park City slopes, this Autograph Collection Hotel (part of Marriott International) exudes an old-world ski-resort vibe, with a grand lobby featuring soaring ceilings, exposed-wood beams, and a stone fireplace surrounded by leather club chairs. The same rustic elegance extends to the 100 suites, each of which comes with its own fireplace, jetted tub, and private balcony or patio for enjoying a glass of wine alongside views of the Wasatch Mountains or 18-hole Park City Golf Course. Start the day with some laps at the outdoor heated pool or hit the slopes, then experience après-ski bliss in the 10,000-square-foot spa, which includes herbal-infused steam rooms, a dry cedar sauna, and recovery treatments like a therapeutic mineral soak and reflexology foot massage. There are also two on-site restaurants—Ruth’s Chris Steak House and the more casual Bandannas Bar & Grill, where you can pair quinoa burgers with local brews.

Just steps from Pacific Beach Park, Tower23 Hotel has embraced its stunning location to the fullest. Modern rooms and suites reflect inspiration from their natural surroundings. A palette of muted colors translates into a tranquil atmosphere, while teak furniture reinforces beach vibes. If you forget anything, sunscreen and baseball hats are available for purchase in the rooms. New-age features such as chromatherapy baths and electronic “Do Not Disturb” signs set the property apart.

By day choose from a number of nearby recreational activities, including surfing, golfing, fishing, and jet skiing. Hotel staff can help you arrange more adventurous options such as a hot air balloon ride or a yacht charter. In the evening check out JRDN restaurant for its floor-to-ceiling glass beach lookout. This coveted sunset viewing location is best experienced with a cocktail in hand. Don’t leave too hastily, though; the restaurant serves equally memorable California cuisine in a laid-back setting.

Flagstaff, Northern Arizona‘s winter-playground-college-town, is often overlooked as visitors drive through it on their way to or from the Grand Canyon. But if you have time to linger, this town will reveal its charms. In recent years, it’s become a regional mecca for farm-to-table dining, with new restaurants repopulating its 19th-century downtown. After getting your fill of locavore dining and microbrews, work it off by going for a run or a hike up on McMillan Mesa, an ancient lava flow with superb views of the San Francisco Peaks, the highest mountains in Arizona. Buffalo Park has a two-mile loop through grassland and ponderosa pine forest, connecting to trails that go up into the wooded slopes. Remember, though, that Flagstaff is over 7000 ft/2133 m. above sea level--give yourself time to acclimate to the lower oxygen levels...

The city’s most famous snowbird, architect Frank Lloyd Wright, spent winters at his home and architecture school in the Sonoran Desert. Taliesin West brings the horizontal lines and organic materials of Prairie School design to the desert landscape in low, skylighted buildings. Behind-the-scenes tours visit the pop-up structures that students have designed as living spaces amid the barrel cactus and paloverde trees.

The Seattle Great Wheel, completed in June of 2012, is located at the Seattle Waterfront. It is a little expensive, and nerve-wracking on the way up, but it’s worth it. The Ferris wheel is one of the biggest in the U.S., and provides a spectacular view of Elliot Bay, Downtown, and much more. In addition, at one point during the ride, it actually goes over the water!

Philadelphia is an ideal destination for lovers of outdoor spaces and beautiful art. Combining the two is the city’s Mural Arts Program, which was originally developed in 1984 as an anti-graffiti initiative and which has blossomed into one of the nation’s largest public-art projects. Buildings and neighborhoods all around the city have been transformed and revived by the colorful works. The program collaborates on 50 to 100 new public-art pieces each year, providing opportunities for thousands of participants of all ages. There are more than 3,600 artworks covering structures in every district of the city. Tours sponsored by the Mural Arts Program are the best way to view the highlights of the citywide “collection” of outdoor canvases.