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A couple of years ago, on Black Friday, my wife and I headed away from the malls of Tucson and into the mountains: Chiricahua National Monument, just west of the New Mexico border in SE Arizona, was one of the last strongholds of the Chiricahua Apaches, who called this area “the land of standing-up rocks.” This particular mountain peak is Cochise Head (elev. 8087'); cock your head to the right and it resembles a man’s profile. The ‘eyelash’ is formed by a tall Douglas fir tree. The volcanic formation is named after Chief Cochise, who died in 1874. About a decade after his death, several hundred of his surviving fellow Apaches were deported to Florida, never to return to their homeland again... The history of the American Southwest is a sobering mix of people on the move with conflicting labels: pioneers/invaders, defenders/terrorists, war/genocide, natives/aliens...It still hasn’t been all sorted out.

What do Al Capone and Bruce Willis have in common? They both did time here at Eastern State Penitentiary. (OK, Willis wasn’t an inmate, but he did shoot the film 12 Monkeys here.) The facility’s first inmate was brought through these doors in 1829, and the prison was in use until 1971. After closing, it became a target for vandals and housed a sizable colony of stray cats. Real estate developers proposed repurposing it as condominiums (high-security, of course), but preservationists won out. They raised funds to stabilize the crumbling interior and remove trees that were growing inside some cells. Wander through its stark interior and learn about the fascinating history of this unique site and its previous tenants, including Capone. Don’t miss the special art installations that are on display here all year round.

Four hundred years of playful history—that’s the purview of the Princeton Doll and Toy Museum, which has a collection of antique dolls and toys from the United States and abroad. Among its holdings are a rare papier-mâché clapper doll and papier-mâché ladies, as well as a “stump doll” that is believed to be nearly 600 years old. In addition to dolls and vintage toys, the museum exhibits feature miniature doll house rooms and all sorts of doll accessories. A research library, gift shop, and appraisal and restoration services are also on-site.

South Point on the Big Island is the most southern point in the United States. The cliffs were ancient mooring places for canoes belonging to the first settlers on the Big Island. Fishermen still use this place to cast their lines, and adventurous locals dive into the turbulent but clear waters below (not recommended for tourists who are not aware of ocean currents, as the undertow is usually quite strong and has swept many lives away in the turquoise clear waters). Several miles up the beach (toward the Hilo side of the Island) is the Green Sand Beach colored by olivine that formed as part of the volcanic eruptions long ago. It is worth hiking to (or paying for a local to drive you in their 4x4). Green Sand Beach is one of only four green beaches in the world.

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.

Bavaria meets Florida at this Marriott Autograph Collection property, midway between downtown Orlando and the theme parks, and close to the Orange County Convention Center. The hotel’s unique decor pairs antlers and fake fur with pastels and palm trees, and adds elaborate chandeliers and original artwork throughout. Accommodations have fairy tale–inspired carved headboards and marble bathrooms; book a corner room for a separate seating area—in a turret overlooking the lush grounds. The Poseidon spa pampers you like royalty with body, skin, and beauty treatments that employ ocean-derived ingredients, and massages can be arranged in room or in the garden. Breakfast and lunch are served at the bright and airy Garden Bistro, with dinner and drinks available in the Antlers Lounge, but you can walk to restaurants and attractions along International Drive, including the Orlando Eye Ferris wheel. Just be back before dark: From the Sky Terraces, guests have views of nightly fireworks and may spot another nearby castle—Hogwarts at Universal Studios.

The Florida Everglades is certainly one of the most unusual places to find a winery and brewery, but Schnebly Redland’s Winery excels in both arenas in what some would call “the middle of nowhere.” Guests are greeted by a stunning wine bar ahead, a beer bar to the right and a counter on the left that sells cheeses and snacks. You can also buy any of the selections you’ve imbibed, either bottles of wine or growlers of beer. The wines are unique, made from local fresh fruits like mango, guava and lychee and made on premises. Schnebly’s beers, brewed for Miami Brewing Company, are equally exotic, with brews like the Big Rod Coconut Ale or the Shark Attack Mango Wheat Ale. Tastings start at $7 and go up if you want to keep the glass. Tours of the facilities are available on weekends.

Just 30 miles from the southern gate of Zion National Park, Quail Creek State Park surrounds a 600-acre reservoir that boasts some of the warmest waters in Utah. Its consistently mild climate draws year-round tourists and day-trippers eager to boat, fish, and swim in the clear blue water. The park is also home to a spacious campground, which proves a popular alternative for Zion visitors who want to stay in a red-rock-desert setting.

When traveling to Miami, it’s important to get a taste of the Cuban culture that started this community decades ago. To immerse yourself in Latin music and Cuban tradition, head to Hoy Como Ayer, a high-end Cuban nightclub in Little Havana. The wood-paneled walls are adorned with portraits of music icons like Celia Cruz and Benny More, stained glass and picturesque old Cuban ads. On any given night you might see one of the best musicians and acts in the Latin Music scene. The most popular event Spam Allstars on Thursdays, where you’ll see the house band perform Latin-fusion music on a small stage at the front of the bar. You might even see a Latin celebrity or two hiding in the corners.

For a taste of the good life, head to South Beach, known for its Art Deco hotels lining Ocean Drive and Collins Avenue, glittering nightlife, and see-and-be-seen vibe. The long stretch of beach, starting with the pier at the top of historic Washington Avenue, is a great place to take in the Miami of postcards and enjoy the sunset over the cityscape. This is where you’ll find some of Miami’s best shopping, top-tier nightlife, and award-winning restaurants, not to mention great people-watching and luxury-car spotting.

Goblin Valley State Park is famous for its series of mushroom-shaped rock formations, also known as hoodoos. While there are a few established trails within the park, the namesake attraction offers three square miles of open landscape, which visitors are free to explore on their own. Beyond the Valley of Goblins, there are seven miles of easy-to-moderate mountain-biking paths, which make five separate loops in various corners of the park. Since it’s so far from any population centers, the area also offers incredible stargazing.

Arizona’s best hotels are as varied as its landscapes. Everywhere from the Grand Canyon to downtown Phoenix to Camelback Mountain, you’ll find glamping retreats, dude ranches, spa-centric stays, historic hotels, and even boutique properties with design-forward guest rooms. Whether you’re seeking a kid-friendly spot for a family road trip or a secluded resort for a romantic getaway, you’ll find it all in the Grand Canyon State.

At Salt Water Farm, students return to the land—and the sea—to learn forage, fillet, and feast.

New Mexico has the reputation for 364 days of sunshine every year. But occasionally it snows a lot, blanketing and softening the rocky scenery New Mexico is so famous for. Ghost Ranch is a conference center about 50 miles northwest of Santa Fe, made famous by Georgia O’Keeffe, who lived in Abiquiu for many years and painted almost every formation with her unique style. You can stay at Ghost Ranch or nearby Abiquiu in one of several B&Bs. For more information, consult the Ghost Ranch website.

The Aubrey sits at the edge of Barrio Bellavista, a few steps from Santiago’s bottle-green 1925 funicular (which takes visitors up to Cerro San Cristóbal) and just below the zoo (sometimes guests can hear the animals when they’re lying by the pool). Open since 2010, this 15-bedroom boutique hotel is housed between two 1920s mansions built by the same architect. The larger of the two houses once belonged to famed Chilean railway magnate Domingo Durán. Today, the hotel is owned by a Brit and an Aussie who spent $3 million and several years transforming it into its current state.

The bedrooms are split between the two mansions, and there’s also an outside block housing a few pool suites. A cobbled terrace runs between the restaurant and piano bar. The interiors are inspired by the early 20th-century art deco movement and feature statement art deco furniture, printed fabrics, and elaborate wallpaper.