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  • 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.
  • Ocean Drive
    Creamy travertine floors and castle brick walls of pearl-stone tiles fuse with Asian antiques and dark teak furniture in the Caribbean-meets-Indonesian design at Villa Balinese, on an elevated crescent fronting Providenciales south shore. From the original local art to the antique Moroccan vases and curved bamboo chairs, it makes a bold and seductive statement throughout -- and best of all, every piece of furniture in this villa rental is hand-picked and meticulously placed by its owners. With just three bedrooms, but 4,200-sq-ft of space and 30-foot vaulted ceilings, it’s impossible not to be transfixed by the Alice-in-Wonderland dimensions and sexy stark vibe encountered here. Entering the grand entrance foyer, the eye is drawn almost immediately to the impressive sunken living room, where a wall of floor-to-ceiling glass windows slides open onto a grand marble pool terrace with panoramic ocean views. The infinity pool running the length of the house was constructed with emerald-colored tiles, creating a vibrant contrast with the turquoise-hued sea it disappears into. A 50" plasma TV, which can be raised with a remote click from a recessed hiding place and swiveled to face the pool, is another one-of-a-kind design example. There is no beach access on-site, but the crystal-clear sea running parallel to the property can be reached via a ladder dock. Please note that children under 12 are not allowed, but this property works great for couples or older families.
  • 424 Eaton St, Key West, FL 33040, USA
    The tiny Flaming Buoy Filet Co. is located down a residential street (walk or come by cab—you won’t find parking), so it feels removed from the crowds along Duval Street. From the simple menu, popular items include the appetizer trio plate (small servings of lobster macaroni and cheese, grilled shrimp with spicy lime chutney, and a caprese salad) and any of the fish specials. A lot of regulars choose the lobster macaroni and cheese as an entrée, too. Dine outside on a porch strung with twinkling lights, or opt for inside the mellow and air-conditioned dining room or at the bar. Reservations are strongly recommended, even in the off-season.
  • 430 Park Ave, Laguna Beach, CA 92651, USA
    Deemed the second-smallest Catholic church in the world by the Guinness Book of World Records in 1983, St. Francis by the Sea clocks in at just 1,008 square feet, with room for just 42 people at Sunday mass. While it’s certainly diminutive, it more than makes up for its size in charm. In addition to hosting regular services, the church is home to the National “Sick Call” Set Museum, which features kits from as far back as the 1880s that were used to perform last rites. In the choir loft, visitors can peruse everything from crucifixes and bowls for holy water to devotional items like statues, then head downstairs to ogle the church’s beautiful stained-glass windows and wood-beamed ceilings. Though St. Francis doesn’t hold regular hours, guests are welcome following Sunday mass or during larger Laguna Beach tours.
  • 1977 Maybank Hwy, Charleston, SC 29412, USA
    Just through the heavy wooden doors of this Sichuan pop-up-turned-brick-and-mortar is the Pour House, an always-busy music venue where early evening soundchecks often fill the dining room with drum and bass noise. Even louder are the explosive flavors on the plate—the kitchen is unrepentant about not toning down the spice on the Sichuan beef and Yu Xiang pork slivers. For the full lip-numbing cocaine-face experience, start with the dry-rubbed Shaoxing chicken wings, which balance sweet, salty, savory, and spice with plenty of crunch. A few noodle bowls are adaptable for the more spice averse, but this is a place for adventurous fire hounds. On Sundays, brunch offers one of Charleston’s only dim sum experiences, including plenty of dumplings, scallion pancakes, and turnip cakes. After a meal, head to the Pour House deck for free daily concerts by local bands, before bigger-name bands take the indoor stage at night.
  • Schlosshof 1, 69117 Heidelberg, Germany
    Perched picturesquely on a rocky hilltop overlooking the city, Heidelberg Castle is enigmatic, romantic, and one of the few castles in Germany that hasn’t been fully restored. Dating back to the 1300s, it served as the seat of the Palantine electors for several centuries. While it expanded substantially during the 16th and 17th centuries, it was plundered and destroyed on many occasions and now consists of mainly Renaissance and Baroque ruins. It’s free to roam the gardens and exterior, but guests must pay an admission fee to visit the interior. Take a guided tour for a historic overview and access to highlights such as the English Wing (built in 1612 by Elector Friedrich V), the graceful Renaissance courtyard, and impressive rooms like the Knight’s Hall and the Imperial Hall. The Grosses Fask (Great Cask) in the cellar is also worth seeing—the world’s largest functioning wine barrel, it’s made from 130 oak trees and can hold some 58,117 gallons of wine.
  • Calle Padre Billini 252, Zona Colonial, Santo Domingo 10210, Dominican Republic
    At this luxury collection of six historic homes—some from the 16th century—guests can book a bedroom or an entire house, all within blocks of Santo Domingo’s most important attractions. You won’t find out which room or home you’ll be staying in until your arrival, but you’re sure to be pleased. Located in the heart of the Zona Colonial, the casas are exquisite. Two were part of former convents, one was a monastery, and another was once the private home of a famous Dominican fashion designer. Each one features unique decor and its own courtyard, and five of the six have private swimming pools. Upon check-in, you’ll receive a loaner iPhone to communicate with your house butler and the round-the-clock concierge team, who can help arrange excursions like culinary tours in the Old City and visits to one of the Caribbean’s largest organic cocoa producers.
  • 1909 India St, San Diego, CA 92101, USA
    Opulent is the word that may occur to you as you stroll into this split-level steakhouse. The art deco-inspired main dining room features oak pillars, camel-colored banquettes, and a jaw-dropping six-tiered brass and crystal chandelier. Upstairs, diners sit on a teak terrace with views of the San Diego skyline. A meal here often includes a show: Many dishes from caesar salad to Tournedos Rossini are prepared and served tableside from custom-made carts. The star of the menu is the Creekstone Farms Beef which has been dry-aged in a glass-enclosed meat locker for more than 25 days. Dry-aged duck and lamb, vegan tartares, and vegetable side dishes like leeks roasted over coals, or broccoli with salty bagna cauda round out the menu. Executive Chef Jason McCleod earned two Michelin stars working at Ria at the Elysian in Chicago. While Born & Raised is a high-end venue, the service is friendly and laid back with suit-clad servers sporting sneakers.
  • 1435 Simonton Street
    Just a few blocks from the bustle of Old Town and Duval Street, this Caribbean-style resort is a serene retreat with a swath of white-sand beach, a pool concierge, and a private pier for fishing or gazing out over clear turquoise waters. All of the contemporary rooms and suites are generously sized and have private balconies with views of the pool, courtyard, or ocean, but the real draw remains right outside your door. Guests can snorkel off the shore, face off on the giant chess board, or simply sway between two palms in one of the beachside hammocks. They also have privileges at sister resort Casa Marina, just up the beach, including at the oceanfront Spa al Mare. Have kids in tow? The hotel offers a full roster of activities, plus babysitting services for parents who want to hit the town.
  • 600 Fleming St, Key West, FL 33040, USA
    Located on Fleming Street in the heart of Old Town Key West, the Marquesa has everything you might expect from a romantic coastal-Florida retreat. Wide porches overlook lush gardens and a bijou pool at the center of the complex, and brick paths shaded by large palms and tropical foliage give the 1884 Greek Revival–style property a secret hideaway feel. It’s understandable if you want to hole up in the guest rooms, which reside in traditional clapboard conch houses and are furnished with an eclectic collection of wood pieces sourced from around the world. In 2018, Marquesa 4-1-4 opened across the street, featuring a new compound of three buildings around a central swimming pool and courtyard. After a day spent exploring nearby Duval Street, make your way back to Café Marquesa, which is perennially packed with locals and visitors enjoying fresh seafood and an inventive menu.
  • Perched on a hill between the busy Zona Sul and hip Santa Teresa neighborhoods, Casa Marques is an all-suites boutique hotel with unparalleled views of Rio. The French-Brazilian couple behind the property blended minimalist modern design with contemporary Brazilian art, creating a space that’s as sleek and subtle as a gallery. Stark white, rooms are decorated with unique local art and artisan-made rugs. Standard suites feature pingo de riga (floor-to-ceiling), wood-framed windows, while master suites include a balcony and expanded bathroom with soaking tub. On the roof of the colonial mansion, there’s an infinity pool and bar overlooking Guanabara Bay, Sugarloaf Mountain, and Christ the Redeemer. Rates include breakfast on the terrace or in the warm, stylish kitchen lounge, complete with traditional tapioca and Brazilian iced tea. Note that Casa Marques’ stellar scenery means it’s challenging to access—plan on taking taxis whenever you can tear yourself away from the hotel vistas.
  • Nahmani St 25, Tel Aviv-Yafo, Israel
    This beloved boutique hotel in the center of Tel Aviv is named after Norman Lourie, the South African-born renaissance man who became not only a “one-man film industry” in Israel, according to a 1948 issue of Variety, but also the nation’s first luxury hotelier. It comes courtesy of Lourie’s son, who bought two adjacent buildings off King Albert Square—both designed in the 1920s Eclectic style—and had them painstakingly transformed into a modern urban retreat. Guests of the hotel can look forward to a rooftop infinity pool, a Japanese tapas restaurant with gorgeous views, a lengthy menu of unique excursions, and, of course, the Norman Series—a monthly event at the Library Bar, during which you can catch various leaders (think diplomats, economists, artists, and scientists) in conversation. Rooms here are equally singular; no two are alike, though all feature Frette linens, beautiful bouquets, and homemade treats at turndown.
  • Nik. Nomikou (Main Street), Oía 847 02, Greece
    Nothing says Santorini like an aqua-blue infinity pool, and Katikies has three of them—all the better to take in westward-facing sunset views. Carved out of the cliff side 300 feet above the Aegean, the hotel’s public spaces are connected by a series of bridges and Escher-esque stairways as they descend from the town of Oia above it. Cube-shaped rooms and suites are minimalist but inviting, nearly every surface painted or clothed in calming white; all have verandas, while a few large suites have outdoor plunge pools or Jacuzzi tubs and alfresco seating areas. Upon check-in, guests are given cell phones to summon 24/7 service from anywhere on the property. They use them to order light snacks at the poolside bar and restaurant or make reservations for some of the best sushi on the island at the champagne bar, but the candlelit rooftop restaurant—serving Greek and Anatolian cuisine—is about as romantic as it gets.
  • Chiang Mai, Mueang Chiang Mai District, Chiang Mai, Thailand
    Nestled within the paddies of a fully operational rice farm, the Four Seasons delivers an immersive experience that’s steeped in tradition. When not exploring Chiang Mai’s ancient temples, guests can learn how to make regional curries at the resort’s cooking school, help farmers plant rice sprouts, or bike through leafy grounds overlooking Doi Suthep mountain and the Mae Rim valley. The 99 elegantly appointed guest rooms, each with teak flooring and Siamese artwork, offer a plush landing spot come evening—that is, if a lemongrass-infused massage at the spa doesn’t do the trick. The resort also has something no other hotel does: two resident water buffaloes.
  • 445−3 Myōhōin Maekawachō, Higashiyama-ku, Kyōto-shi, Kyōto-fu 605-0932, Japan
    In an area rife with traditional, minimalist ryokans, the Four Seasons Kyoto is a spectacle of grandeur. The opulence is subtle, however, camouflaged by clean, Zen-like style. At the hotel’s heart is a beautiful, 800-year-old pond garden, which features a picturesque teahouse surrounded by cherry, maple, and willow trees. Inside, luxurious details abound, from the seasonal floral arrangements, to the iPads and in-mirror TVs in the guest rooms, to the plush cabanas and atmospheric lighting at the underground pool. For even greater indulgence, guests can head to the spa for such treatments as sake baths, bamboo-and-green-tea scrubs, and jade-stone massages, as well as facials from cult French brand Biologique Recherche. When hunger strikes, the Michelin-starred Sushi Wakon is waiting. Helmed by master chef Rei Masuda, the 10-seat restaurant serves fresh fish, flown in daily from Tokyo’s Tsukiji market.