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  • Carretera a Tlacolula 190 Km 17, San Jerónimo Tlacochahuaya, Oax., Mexico
    This small archaeological site is situated on a hillside about 12 miles east of Oaxaca city. The name “Dainzú” means “hill of the organ cactus” in Zapotec, although that most certainly was not the original name. The site was occupied in very early times, but its apogee was roughly at the same time as Monte Alban (200 B.C.E. to 350 C.E.). It was excavated in 1965 by Mexican archaeologist Ignacio Bernal. This is one of Oaxaca’s less visited sites, so you’re likely to have the place to yourself. It is quite a nice site, however, and worth a visit for a few special features. The site has a ball court, as well as a gallery of bas-reliefs depicting ball players, so undoubtedly the game was very important to the inhabitants. Another must-see is a tomb that has a jaguar carved into the entrance; the face is carved in the lintel, and the animal’s forearms are on either side.
  • Pilos 240 01, Greece
    In Greek mythology, Heracles slew all the sons of the King of Pylos except Nestor, who became king of Pylos himself. Nestor appears as a sage elder in both the Iliad and the Odyssey, expounding on how things were really tough back in his day. If you visit Voidokilia Beach, about 12 kilometers (7.5 miles) from Pylos, you can take a 15-minute walk to see Nestor’s Cave. First, enjoy your time on the beach, which is renowned for its natural beauty. Then climb over the dunes at the beach’s southwest end and follow the hillside path to the cave, which sits just below the ruins of the Paleo Kastro, the old Pylos castle. As legend has it, this cave is where Hermes hid the 50 cattle he stole from Apollo. The trip is worth it for the views alone: The higher you go, the more you’ll see, as the panorama takes in Voidokilia Bay, the Gialova lagoon, the Bay of Navarino, the Peloponnesian hills and the city of Pylos.

  • Jennings Extension, St. Mary's, Antigua
    By law, every beach in Antigua is public. But at this all-inclusive resort surrounded by 140 acres of undeveloped land on the island’s west coast, guests feel “their” beach belongs almost exclusively to them. The hotel is a 35-minute drive from the airport, and it’s accessed by an unpaved road. Seclusion is a big part of the appeal at this adults-only (except in July and August) hideaway. Its 27 minimalist but spacious cottage suites begin on the beach and are scattered up a hillside that overlooks a picture-perfect bay. All the cottages have outdoor showers, king-size beds with mosquito netting, and at least a partial view of the sea. Expect to see a lot of honeymooners and other romantically inclined couples here, but don’t expect to see much of them, except at meal times, when the foodie-approved mix of European, American, and Caribbean dishes draws out even the most recently married.
  • KM 4 - Apalta Colchagua, Santa Cruz, Región del Libertador Gral. Bernardo O’Higgins, Chile
    Located just outside of Santa Cruz in the heart of the Colchagua Valley, Clos Apalta Residence (formerly Lapostolle Residence) is known for its premium Chilean wine. In 2005, the Marnier family opened the stunning property on a steep hillside in the micro region of Apalta. In addition to a state-of-the-art, gravity-fed winery, they built four villas, giving wine lovers a unique place to stay. Today, Clos Apalta functions as a Relais & Chateaux luxury hotel, complete with beautiful views of the valley and its surrounding mountains. Guests can relax on their private terrace, in the lodge, or by the infinity pool, sipping house wines while enjoying the vistas. They also have exclusive access to the dining room, where chefs use produce from the hotel’s own organic garden, and tours of the owners’ wine cellar during visits to the winery.
  • St John's, Antigua and Barbuda
    The moment you walk into Buba’s, you feel like family. It’s easy to understand why when you consider that surrounding this blink-and-you’ll-miss-it hillside restaurant are Buba’s house, Buba’s sister’s house, and Buba’s Brother’s house across the street. Buba’s own two daughters, nephews, cousins, and other miscellaneous family either host, help in the kitchen, play dj, man the bar, or simply greet visitors from their porches with welcoming, West Indian waves. This homegrown approach extends beyond hospitality to deliciously impact the food as well. Nearly every fruit, vegetable, and herb used in the dishes at Buba’s are all grown on the sloping overgrown gardens surrounding the restaurant. The result is a quintessential island restaurant with no real set menu. Instead, expect the freshest ingredients of the day lovingly coaxed into a collection of authentic Caribbean fare like rice and peas, stew chicken, steamed veggies, salad, and more.
  • POB 487, 44850 Comptche Ukiah Rd, Mendocino, CA 95460, USA
    The terraced organic garden that steps down the hillside in front of the Stanford Inn (above Mendocino Bay) provides some of the vegetables and herbs for the innovative cuisine in the hotel’s Ravens’ Restaurant. A stroll through the farm, with a visit to the donkeys and horses and llamas, helps work up an appetite for the vegetable-based whole-food meals that raise the bar on all-vegan fine dining. Innkeeper Jeff Stanford puts his ethics on the plate: Vegan for both health and philosophical reasons, Stanford collaborates with certified nutrition consultant Sid Hillman and the Ravens’ chefs to create dazzling meals, including one of the most innovative and tempting brunch menus I’ve ever encountered. The Inn, a large boutique hotel with panoramic ocean views, an organic farm, luxury amenities, and a bookstore and wine shop, gains additional points for being dog-friendly--even in a special dining area.
  • Unnamed Road
    I love staying in a private villa home over a hotel when traveling with a small group, and Breezy Villa by Island Escapes is both affordable and impressively chic. In a secluded hillside location, complete with multiple, swaying palms for privacy and glassy sea-foam green lagoon views that are just a shade lighter than the infinity pool melting into them, it’s easy to check skinny-dipping in paradise off the bucket list when sleeping here. If naked swimming isn’t your thing, no worries, the pool is also perfect for nighttime stargazing floats. And then there is the leeward lagoon location itself -- it is super calm and you can wade for ages through calm and crystalline water here without gaining much depth. There is no direct beach access, but a series of steps wind their way down from the travertine-tiled pool terrace to a small pier where a ladder offers direct sea access. Breezy Villa’s stylish interior is equally appealing. From the arched doorways and pitched roof in the open living room and modern L-shaped kitchen to the square-shaped original ocean-hued paintings hung on either side of the front door to the Grecian-Roman columns on terrace, I love the Zen beach house meets Italian palazzo vibe. Similar-sized sleeping quarters, each featuring a unique wooden bed frame and French doors opening directly to pool terrace, make this three-bedroom home equally perfect for families, especially those traveling with a nanny. It also works well for multiple couples.
  • 4 Via Vallelunga
    There is a reason why renting a villa in Tuscany is so popular - rustic farmhouses, rolling hills filled with olive and plum trees, golden sunsets, locally-harvested wine, creamy cheeses, and cool evenings spent with friends and family. Renting a villa provides a relaxing base for your sightseeing in the region. Almost all Tuscan towns allow easy day trips to the main sights: - Florence‘s art and Renaissance history (Duomo, Uffizi Gallery, Michelangelo’s David) - Cortona’s steep, narrow streets and medieval walls - Siena’s cultural city center, now a UNESCO World Heritage Site - San Gimignano’s fortified towers set amidst picture-perfect Tuscan hillsides - Montelpulciano’s world-famous wineries and more This offers the best of both worlds - after a dusty day of sightseeing, you can relax at your villa with a jump in the pool and a glass of wine. Watch the sun go down in a purplish haze, unwind with friends, and enjoy the lovely moment. I recommend YourTuscany.com, which is where we found Villa Coloniale (above) in the town of Pergine Valdarno. The infinity pool and covered patio are guaranteed to put you in a relaxed, Italian frame of mind!
  • Vagia Beach, Serifos 840 05, Greece
    While the Cycladic island of Serifos has stayed blissfully under the radar for most tourists, savvy Athenians have been quietly snapping up property while preserving its dusty charms. COCO-MAT Eco Residences, opened by the eponymously named Greek sleep-product company, is emblematic of this mindset: Its 13 rooms were reclaimed from stone miners’ houses built in 1910 at the foot of a hillside, just steps from the sand and calm waters of Vagia Bay. The one- or two-bedroom units feature bedrooms on the (cooler) bottom floor and living spaces and kitchenettes above (they’ll do the grocery shopping); you choose your mattress preference from the brand’s sustainably made line. Carved into the cliff face, the Lounge Bar serves buffet breakfast in the morning, lunch and light snacks during the day, and dinner in the evening—including right on the shore (for an additional charge). The hotel also supplies car or motorcycle rentals should you want to explore the island, and also will arrange diving trips and excursions to different beaches.
  • Piazza dei Mulini, 23, 84017 Positano SA, Italy
    Formerly the private residence of Gioacchino Murat, king of Naples and Napoleon’s brother-in-law, Palazzo Murat has the mark of aristocracy—white-walled interiors are outfitted with elegant antiques, oil paintings, and decorative tiled floors—but also the welcoming atmosphere of a dear friend’s home. The 18th-century villa is tucked away behind cascades of bright bougainvillea and greenery-filled grounds fragrant with jasmine and citrus trees yet centrally located in Positano’s pedestrian zone, making it an ideal base for shopping holidays and seaside idylls alike. The pool is especially impressive, flanked by a lawn studded with chic sunbeds and backed by a storybook scene of pastel-hued houses stacked higgledy-piggledy along the hillside. Just steps away is the charming Al Palazzo restaurant, which incorporates ingredients from its vegetable patch and twinkles with candlelight in the evenings. As for the guest rooms, soothing white spaces are accented with pops of blue and lemon yellow, and French doors open onto lovely balconies with views of the gardens, town, or sea.
  • Costa S. Giorgio, 2, 50125 Firenze FI, Italy
    The Bardini Garden is one of Florence‘s best kept secrets. It was built in the 12th century as part of a large estate owned by the Mozzi family. During the 20th century it was closed for many years and only reopened in 2005 after significant restoration. The garden is small and easy to walk through in about an hour and its hillsides offer spectacular views of Florence. Wandering among the terraces and flowers is an excellent way to escape from the touristy historic center and instead feel part of what this old city once was. During the off-season and in the morning or late afternoon, you may be the only visitor! The Bardini Garden can be accessed in two ways. One is by going into Boboli Gardens and exiting on the left side—this can be hard to find, but is marked on the Boboli Gardens map you receive on admission. The second way is via street da Costa San Giorgio 2. The garden opening hours vary according to season. It is closed the first and last Monday of each month. Admission is included in the Boboli Gardens ticket, or can be purchased separately for around 10 euros (and includes admission to the villa). There is also a restaurant with beautiful terrace views.
  • 25250 La Paz Rd, Laguna Hills, CA 92653, USA
    When this wine country–style restaurant opened in the Laguna Hills in 2016, it was instantly embraced by locals. Maybe it’s the hillside location—no bikinis in sight—that allows diners to breathe easy and indulge. Maybe it’s the warm wood-clad dining room with its lively open kitchen. Or maybe it’s the craft cocktails and 25-plus international wines poured by the glass. Regardless, Ironwood is not the place to come while on a diet. The biggest reason: the house-made giant meatball, served with fresh, made-from-scratch herb pappardelle, spicy pomodoro sauce, and ricotta salata. Limited numbers are made each night, so it’s worth going early (the dinner-only restaurant opens each evening at 5 p.m.). The menu also features American Wagyu burgers, mac and cheese skillets, and pork shanks with fried green tomatoes and fresh burrata—plus colorful, palate-cleansing salads incorporating handpicked local ingredients. When the weather’s good, a retractable roof is pulled back from the heated patio to reveal views of the picturesque Saddleback Mountains. Must-order: the warm fromage blanc brownie with Nutella ice cream.
  • 50135 Settignano, Metropolitan City of Florence, Italy
    The Belmond Villa San Michele knows something about history. Michelangelo designed its facade, Franciscan monks tended its gardens, and Brigitte Bardot stayed here. But, like any elegant host, it’s not brash about its pedigree. Manicured Italian gardens—designed by 15th-century friars—beckon you for sun-soaked strolls. The colonnaded loggia is a pleasant place for a sunset aperitivo or candlelit dinner, especially with a view of Florence and the Arno Valley. The hotel’s expansive rooms are already decked out in the most tasteful, almost understated interpretation of Renaissance luxury—terra-cotta tile floors, heavy wood furnishings, just a dash of red velvet, and plenty of cream-colored walls—and then the panoramic views, original frescoes, and modern Carrara marble bathrooms steal the show. There’s a real-deal cooking school, where the chef actually works with each person in hands-on preparations—no demonstrations-only here. Other perks include the hillside pool, the concierge service that can get you into the Uffizi outside of operating hours, and, from the Loggia Restaurant, a view of the ancient Roman road that once connected Florence to Fiesole.
  • Via Alberto Cadlolo, 101, 00136 Roma RM, Italy
    The Rome Cavalieri, like the Hassler and St. Regis, is synonymous with five-star luxury in Rome. The hotel, opened in the 1960s, channels a Versailles-meets–Dolce Vita vibe, and given its unbridled opulence, it’s a top destination for honeymooners and jet-setters seeking the ultimate comforts. Its location atop Montemario, a hillside residential district north of the Vatican, offers spectacular views of the city from various terraced levels and many of the rooms. The very location, affording such panoramas, is also a drawback for travelers wishing to be in the thick of it all, so the Rome Cavalieri is best suited to those who relish spending significant time in the hotel rather than out on the town.

    There are plenty of appealing amenities for guests who choose to stick around the property. The outdoor pools, the finest in Rome, are set amid lush gardens. The pool area doubles as a sort of private club for local elite and is ripe for Italian athlete and celebrity sightings. Back inside, the lobby and rooms are sumptuously furnished and feature antiques and original works of art.
  • Medellín’s urban renewal, following decades as one of the world’s murder capitals, has drawn international attention. Perhaps nothing symbolizes the revival more than the Metrocable, a system of cable cars that connect the city center to steep hillside neighborhoods that were once reckoned to be the city’s most dangerous. Grab a ride on Line K up to Santo Domingo and treat yourself to spectacular views. Once on the ground again, take a short wander around the neighborhood for a taste of the real Medellín and its friendly residents (known as Paisas), and see the small shops and the beautiful library whose original benefactor was the government of Spain. From Santo Domingo, another cable car continues to Parque Arví, an expansive nature reserve and weekend escape favored by overheated locals.