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One of Maui’s best hikes, this trail climbs 800 feet through the lush Kipahulu area of Haleakala National Park. Half a mile from the visitor center, an overlook provides sweeping views of the gorge and the almost-200-foot-long “horsetail” of Makahiku Falls. Continue on past a sprawling banyan, stopping to marvel at the sunlight trickling through the dense bamboo forest. Here, you’ll also find the even more dramatic cascade of Waimoku Falls, which plunges 400 feet down a sheer-walled lava amphitheater. If you’re wary of tackling the four-mile round-trip hike by yourself, know that park rangers offer guided tours every Sunday at 10 a.m. Reservations are available at 9 a.m. a week ahead of time.

A classic New England bed and breakfast with a boutique hotel vibe, the Union Street Inn is housed in an impeccably maintained 1770 whaling captain’s home just off Main Street in downtown Nantucket. A short walk from the Hy-Line ferry and harbor, the inn has a convenient location in town (including parking, a huge perk on the island) and can also outfit guests with beach gear for a day on the sand. A quintessential gray-shingled exterior contrasts with the bright blue chinoiserie patterns and crisp white Frette and Matouk linens in the inn’s 12 immaculate rooms. Union Street’s cherry on top is the made-to-order gourmet breakfast, which might feature fresh peach cinnamon rolls or homemade carrot cake, depending on the season.

Quinto La Huella is the second location of arguably Uruguay’s most famous and best restaurant, the Parador La Huella in the tiny resort town of José Ignacio. On the fifth floor of the East, Miami, hotel, the eatery uses a wood-fired parrilla (grill) and oven to cook nearly everything on the menu. The dining room is wrapped in wood, and the outside dining area is a garden oasis with leafy foliage, great music, and a homey vibe. The burrata, served with fresh figs, prosciutto, and walnuts, is a standout starter, and don’t forget to order smashed potatoes, which are served as they are in Uruguay: The potato is grilled over the fire and smashed right before serving, to retain the natural texture of the vegetable.

Inspired by vibrant Southeast Asian night markets, D.C. chef Erik Bruner-Yang (of Toki Underground fame) and D.C. streetwear mogul Will Sharp created a sleek, two-story indoor/outdoor space that’s part menswear store, part café and restaurant. The first level is all about shopping, and the floor is lined with glass-encased displays featuring Sharp’s clothing line, Durkl, as well as a library full of designer sneakers. Upstairs, sip locally roasted Vigilante coffee while snacking on Frenchie’s pastries and desserts. The best part, though, is when you step onto the patio and take a seat at the open kitchen serving up Yang’s blazing hot and flavorful Cambodian and Taiwanese cuisine. Don’t miss out on the American Wagyu tartare, the Khmer tamarind salad, the steamed pork bao buns, and zha ji pai (Taiwanese fried chicken).

An offshoot of the highly acclaimed restaurant Talulah’s Garden, this neighboring cafe and market offers a casual spot for eating in and gourmet foods and treats for taking out. Located directly on Washington Square park, the cafe serves wine and beer and premium La Colombe coffee. Talulah’s Daily is a comfortable place to enjoy healthy prepared foods and creative sandwiches, with many options for vegetarians. The gourmet shop offers a variety of unique non-perishable food treats that will survive your trip home.

Stretching high above Fifth Avenue, the Peninsula is a glamorous, classic hotel. Formerly the Gotham Hotel (built in 1905), this building is at the heart of prestigious Midtown Manhattan with neighbors like the Museum of Modern Art and Rockefeller Center. It has a convenient location for Fifth Avenue shopping and exploring Central Park. The Peninsula is a favorite of New Yorkers for its rooftop bar, Salon de Ning, with its mesmerizing views of the city skyline. Rooms are polished and inviting, designed to resemble a luxurious New York City apartment. Kick off your stay with a classic cocktail in the Gotham Lounge, followed by a locally sourced meal at the elegant Clement Restaurant and Bar.

Sitting at the entrance to a secluded red-rock canyon eight miles outside Sedona, Enchantment Resort may be the Southwest’s most visually stunning accommodation. And while the indigenous people who originally inhabited the canyon had more elevated views—their cliffside dwellings are visible to anyone who can tilt their head far enough back—it’s doubtful that even they appreciated the scenery more than travelers arriving from worlds of gray skies and cacophonous congestion. There are numerous guest rooms and configurations, all done in a pueblo style and red-rock hue that blends so well with the surrounding canyon that guests who’ve given into the lunchtime temptation of a second prickly pear margarita at Tii Gavo would do well to carry a resort map (which is handy anyway for the many surrounding hiking options).

For over 20 years, this large open-air market only 7 miles north of Santa Fe showcases a variety of local artisans, importers and designers hawking their wares. As all flea markets go, it’s a hit or miss operation sifting from a selection of turquoise jewelry, rugs, clothing and cowboy boots. It’s also weekends only.

One of the most popular new breweries in town, Black Abbey Brewing Company opens its “fellowship hall” tasting room Thursday through Sunday. Have a seat at one of the communal tables for a bite of cheese, olives and meats while tasting your way through beers like The Rose, a belgian-style blonde, or The Special, a traditional monastic-style beer. Black Abbey’s brews also are available at many restaurants and bars in town.

The Morada Bay Beach Cafe on the bay side of Islamorada is the perfect spot for a Keys lunch. Colorful chairs and tables dot the beach; the food is excellent and the restaurant regularly receives fantastic reviews. Try the Wagyu beef burger. It is delicious. Fresh fish and seafood are popular choices. The conch fritters and conch chowder hit the spot. The staff is very friendly, professional, and helpful. Island music or Jimmy Buffet songs waft across the beach.

If you are a fan of mochi, this is a MUST stop on your visit in the Hilo area. The place is tiny, there is usually a long line, takes cash only, and parking is a bear, but once you take one bite into their massive (and most famous) strawberry mochi you will be hooked for life! They have a wide variety of flavors and all the mochi is fresh, dry where it needs to be dry, and with perfectly seasoned filling.

Coffee and espresso are a big part of the road trip experience for many people, though it usually comes quickly through a drive-thru window, or across the counter at a big chain coffee shop. The Big Lodge Espresso shop is different. This giant concrete teepee rests on the outskirts of Browning and serves up some of Montana‘s best coffee, 89-cent pastries, and two-dollar muffins. And, once again, it’s a giant concrete teepee! Get your camera ready.

Step back in time and treat yourself to a thick frosty milkshake at the Parrot Confectionery. Little has changed since its opening in 1922; from the shiny soda fountains to the old-time juke box against the wall, much of the the interior has remained unaltered for nearly a century. The Parrot rewards their customers with delectable treats such as sundaes, malts, homemade sodas, milk shakes, as well as hand dipped chocolates, homemade fudges and caramels.

There are over 100 excellent guest ranches in the Western U.S., offering a range of family vacations. Brush Creek Ranch, in southern Wyoming, is one of the more exclusive properties, offering an enormous range of activities on 15,000 acres of stunning high-mountain ranchland. This is the main lodge building, looking out over the horse pastures.

Cerrillos, New Mexico was the center of the turquoise mining trade in the late 1800’s, and almost became New Mexico’s capital. The Clear Light Opera House was built to house performances by East Coast luminaries like Sarah Bernhardt. One of the ghost towns repopulated by artists along the now famous Turquoise Trail, it’s a great day trip from nearby Santa Fe. Check out the Trading Post, pet a llama, and visit artist Bill Skrip’s sculptures.