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  • Chemin de Quinson, 04360 Moustiers-Sainte-Marie, France
    When one of the world’s most famous chefs falls in love with one of France’s most picturesque villages, the result can only be La Bastide de Moustiers. After chancing upon Moustiers-Ste-Marie, Alain Ducasse promptly bought a secluded seven-room home, which he later turned into an inn and Michelin-starred restaurant. Complete with charming rooms, an idyllic garden, a shady terrace, and a serene pool area, the inn is more than worthy of an overnight, but guests really come here for the restaurant. The three- and four-course menus change depending on what’s fresh in La Bastide’s vegetable garden, but often include such delicacies as tomato sorbet, stuffed zucchini flowers, and seasonal ratatouille. Whether you sit in front of the majestic walnut fireplace in Le Salon Voyage en Asie, or amid local pottery in Le Salon des Arts Décoratifs, you’re in for a magical meal. The restaurant also features a room for private groups and a salon with a single table for couples, making it perfect for celebrating a special occasion.
  • Via Enrico Figari, 38, 16032 Camogli GE, Italy
    Tucked away on the less-trafficked slopes of Mount Portofino, above the picturesque waterfront town of Camogli and scenic Riviera di Levante, Villa Rosmarino is that Italian friend’s vacation house you’ve been dreaming of. Owners Mario Pietraccetta and Fulvio Zendrini left Milanese corporate life to transform this dilapidated turn-of-the-century palazzo into a midcentury-style oasis with touches of Italian modernism, then moved in permanently, inviting others to experience their personal brand of la dolce vita. The library is outfitted with stylish armchairs, warm wood ceiling beams, and a collection of art and travel books that spans the walls, and the living room’s well-stocked honesty bar is the backdrop for friendly nightcaps. Rooms aren’t numbered, and the sprawling gardens are easy to get lost in. Mario and Fulvio are likely to chat guests up while lounging by the pool or sipping espresso on the balcony, offering their insider knowledge about the area and arranging one-of-a-kind excursions, from visits to secluded beach clubs to rides in their wooden motorboat.
  • Charleston, SC 29401, USA
    Waterfront Park runs a picturesque half-mile along the Cooper River, from an exuberant fountain at its north end (near the cruise ship terminal), to North Adgers Wharf at its southern border. There is much to recommend a stop in this small eight-acre space: a great path for running or strolling with expansive views of ships moving in and out of the harbor; a fountain topped with a pineapple sculpture that splashes water into a small wading pool where children are permitted to play; and, also welcome on hot Charleston afternoons, a tree-shaded promenade lined with benches for those in search of a sea breeze.
  • 98 San Jacinto Blvd, Austin, TX 78701, USA
    Set right on the banks of Lady Bird Lake as it passes downtown, the Four Seasons Hotel Austin performs the impressive juggling act of feeling like both a glamorous city stay and a picturesque, elegant resort. On one side is Live Oak, a local hot spot for live music, on the other the sun-lounger–lined saltwater pool that looks out over the sprawling lawn and the lake beyond. This outdoorsy-meets-hip dichotomy is part of what defines Austin, and the hotel is right at the heart of it: Lady Bird Lake Hike and Bike Trail is the closest of many urban trails, and the food trucks and record stores of the trendy Downtown and Bouldin Creek neighborhoods are within walking distance—a rarity in this expansive city.

    A Hill Country–inspired spa and Latin restaurant draw locals, while elegant rooms (updated in 2017) with lake views and signature Four Seasons service—think seasonal lemonade or hot apple cider on arrival and s’mores (weather permitting) on the back patio—make stays extra special.
  • Kalk Bay, Cape Town, 7990, South Africa
    One of Cape Town’s most picturesque corners, this small fishing harbor sees boats sail in daily with their catches (often trailed by hungry seals waiting for tidbits). Recently, however, the area has also become known for its antique stores, restaurants, and shops—one of the best collections of African curios, materials, and artwork for sale can be found at Artvark, on the edge of town. Expect to see everyone from hipsters to surfers to an old couple who’s lived here for 50 years. A seaside promenade connects Kalk Bay to the colorful beach cottages of St. James and to Surfers Corner in Muizenberg, another gem of an old-world suburb that is becoming a second Kalk Bay. Don’t miss Cucina Labia, a restaurant housed in a mansion built by an Italian who wanted to create a little Venice here.
  • 658 Wharf St, Lahaina, HI 96761, USA
    Lahaina, with its many Victorian flourishes, may look picturesque today, but the port town teemed with sailors, gamblers, and prostitutes in the 19th century. The Pioneer Inn changed all that when it opened for business in 1901, foreshadowing the tourist industry that would ultimately replace whaling, sugar, and pineapples. Step through the swinging doors of this vintage bar, which now bizarrely anchors the courtyard of a Best Western, and you’ll be transported back in time. Oars, harpoons, and a ship’s figurehead still adorn the space, looking down on platters of coconut shrimp, Parmesan-crusted fish over coconut rice, and margaritas made with POG (a mix of passion fruit, orange, and guava juices). Come during happy hour, which runs daily from 3 p.m. to 6 p.m., for discounted beers and cocktails.
  • Av El Sol 395, Cusco 08002, Peru
    La Catedral is actually three churches in one, each of which are exquisite. It is decorated in the Baroque style, with more gilt and gold trimming than you can imagine. In order to convert the Incan people to Catholicism, the Spanish used symbols from Incan religion throughout the church. Look for the hundreds of mirrors, as well as the triangle shape associated with the Mountain God. La Catedral hosts a couple of particularly unique pieces, including a Peruvian rendition of the Last Supper featuring a guinea pig as the main dish. El Señor de Los Temblores is a crucifix that stopped the Cuzco earthquake of 1650, and is featured prominently in the cathedral. Pictures are not allowed inside, but the exterior of La Catedral is picturesque both during the day and at night when it’s lit up with the rest of La Plaza de Armas.
  • Długa, 80-826 Gdańsk, Poland
    At just over 540 yards, Długi Targ, which translates to “the Long Market,” isn’t really all that lengthy. Still, it makes for a lovely walk, stretching from the Green Gate at its eastern entrance through the medieval city of Gdańsk to the Golden Gate at its western end. Lined with cafés, restaurants, and souvenir shops worth a stop, the route is also home to picturesque architecture, including historic tenement houses that were renovated after World War II. Be sure to stop at the elaborate 17th-century Neptune Fountain (which represents Gdańsk’s ties to the sea) and, just behind it, the 15th-century Artus Court (a medieval hall fantastically decorated with hunting trophies and models of tall ships hung from the ceiling). A tiny detour down Kramarska Lane behind Artus Court will take you to St. Mary’s, the largest brick church in the world. In this enormous space, which can accommodate as many as 25,000 people, you’ll find a 500-year-old, 25-foot-high astronomical clock, as well as several Baroque statues of angels playing musical instruments. If you’re not afraid of heights, consider climbing the 409 steps to the top of the church tower.
  • 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.
  • South Korea, Seoul, Jongno-gu, Gahoe-dong, 계동길 49-23
    Meaning “a place where one can enjoy the traditions of times past and rest one’s soul,” Rak Ko Jae certainly lives up to its name. Styled after a Chosun Dynasty–era house, the 130-year-old hanok (traditional Korean house) was used by a secret society during the Japanese occupation of Korea before World War II as a place to study and preserve Korean language and culture. In 2003, a master architect, designated by the Korean government as a “Human National Treasure,” renovated the hanok, and now it’s one of the most picturesque places to stay in all of Korea’s capital. Stepping through the gate into the peaceful courtyard feels like going back in time, and the lotus pond, yellow-mud sauna, and traditional Korean cuisine only add to the anachronistic feeling. Guests staying at the small and intimate Rak Ko Jae can take part in many elements of traditional Korean culture such as making kimchi, trying on a hanbok (traditional Korean clothing), or experiencing an afternoon tea ceremony.
  • Via della Scala, 18, 50123 Firenze FI, Italy
    Hundreds of years ago, at the height of Florence’s Renaissance heyday, visitors to this cultural capital wouldn’t have stayed in the kinds of luxury hotels that now line its picturesque streets. Rather, the well-heeled would have come at the behest of friends, lodging in private homes whose unassuming facades in the best neighborhoods belied their sumptuous interiors and private gardens, outfitted with art and artifacts collected from around the world.

    A guesthouse to its core, Casa Howard continues this Florentine tradition; there is neither lobby nor restaurant, and the owner Massimiliano Leonardi di Casalino lives in his own apartment here while in town (note, it can be rented when he’s away). Jennifer Howard Forneris, one of the design-conscious proprietors who has since passed away, was the daughter of renowned textile designer Luciano Forneris. She gave each room its own look, with finds from her and Leonardi di Casalino’s world travels. A media room is the sole common area, and a hammam steam room and an on-site concierge service are the only nods toward traditional hotel services. Insider recommendations are personalized according to guests’ preferences, and the honor bar feels more like a friend’s (well-stocked) fridge.
  • 215 Charles St, Boston, MA 02114, USA
    While the Liberty Hotel may have deep roots in Boston lore, it’s not for the reasons you think. For more than 100 years the hotel existed as the Charles Street Jail, an in-city penitentiary that housed (in)famous inmates like James Michael Curley, Malcolm X, and Sacco and Vanzetti. Its inspired transformation came in 2007, but the owners maintained some of the jail’s vestiges, from the exercise yard to several jail cells, while turning the building into a 298-room luxury hotel. Richly appointed rooms offer sweeping views of the city skyline and the Charles River.

    The hotel houses five distinct restaurant and bar venues, all of which attract large swaths of locals, especially on the weekends. Located at the foot of Beacon Hill, the hotel is steps away from the boutique and antique stores along Charles Street and also sits next to the picturesque Charles River Esplanade.
  • 512 E Washington St, Orlando, FL 32801, USA
    Orlando’s centerpiece lake sits right in the middle of downtown, close to the pretty neighborhood and dining district of Thornton Park. A pedestrian-only path fringing the water stretches for nearly a mile, offering visitors a great place to stroll or jog. Along the lake you’ll also find an amphitheater for concerts and festivals, a picturesque pagoda overlook, and a kiosk where you can rent pedal boats shaped like swans. Bring the kids to feed the ducks and swans, or visit the farmers’ market, which takes place on the lake’s southeast corner every Saturday morning.
  • Piazzale Napoleone I, 00197 Roma RM, Italy
    Encompassing early 200 acres of rolling parkland, Villa Borghese is Rome’s verdant heart and everyone’s favorite place for an afternoon walk. The vast gardens are criss-crossed with picturesque paths, where visitors can meander past ancient statues and fountains, sit by a lake or caffè, and take in a film at one of two cinemas. For culture vultures, there is a Shakespearean Globe Theatre with a robust summer schedule, a historic puppet theater, and several world-renowned museums including Galleria Borghese with its enviable collection of Bernini sculptures and Caravaggio paintings. Younger kids enjoy playgrounds, electric train rides, and a kids museum, while children of all ages can get active with skate, bike, and paddleboat rentals.
  • Sector San José, Castro, Región de los Lagos, Chile
    The first luxury lodge to come to Chile’s second biggest island, Tierra Chiloé opened in 2012 and became a member of the Tierra hotel group in 2014. Designed by Chilean architect Patricio Browne, the hotel looks like a boat on stilts and was inspired by the homes of local fishermen, which take the same form and are known as palafitos. The exterior is made from picturesque larch wood shingles—a building technique that’s very typical on Chiloé and is seen on the famous UNESCO World Heritage churches that dot the islands.

    Inside, guests find more wood. The hotel’s wood walls and ceilings are made from indigenous species . The decorations are locally inspired with plenty of handicrafts such as wicker baskets, handwoven rugs, and wooden carvings. The focal point is the meadow and Reloncaví Sound below, where the hotel’s boat is harbored. Large windows line the building on both floors and provide excellent views. Guests can relax in a small spa, a winetasting room, or a book-filled upstairs studio upstairs. The living room with fireplace makes a perfect spot for an end-of-day pisco sour.