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  • Seven Mile Beach, KY1-1209, Cayman Islands
    With its world-renowned chef and ultrachic decor, Blue—tucked discreetly into the Ritz-Carlton Grand Cayman—seems the sort of place you’d find in New York or Paris. But the main draw is decidedly local: spectacularly fresh ingredients sourced largely from the sea right outside and served up in such specialties as lightly seared wahoo with bok choy and kimchi broth; or poached halibut with sunchokes, salsify, and truffle jus; or bread-crusted red snapper with squid and sofrito sauce. If you’re feeling ambitious, go for the gusto with a six- or seven-course tasting menu—and tack on the wine pairings.
  • Domeyer 366, Barranco Lima, Peru
    Previously the home of Peruvian sculptor Victor Delfin, who still keeps a studio and gallery on-site, Second Home Peru is the guesthouse everyone would want to know about (but doesn’t). The beautifully maintained Tudor mansion is one of the first boutique hotels to open in Lima, though being hidden away in a residential section of the Barranco arts district, few realize it is there. Its neighborhood location is ideal—a few blocks from the lively plaza and from a cobblestone walkway down to the beach, the Bajada de los Baños, that is lined with restaurants. The highlight, however, is the ocean view, as the house is set near the edge of Lima’s coastal cliffs, and several rooms have balconies that look right over the water. The vistas are better from here than from the often-gray skies of the more posh hotels in Miraflores up the coast, and guests can enjoy them from the small outdoor pool, gardens, and shared terraces as well. The eclectic décor includes wood floors, Louis XV–style claw-footed bathtubs, and a small contemporary art collection that lines the halls and stairways. The family-run property isn’t flashy or ultra modern by any means, though flat-screen TVs and Wi-Fi come standard.
  • 61، Rue Sidi el Yamani, Marrakech 44000, Morocco
    In the heart of the medina, not far from the entry to the souks and the main square, two French brothers have transformed a historic riad into an intimate, contemporary Moroccan hideaway. Opening onto two internal courtyards—one of which has a swimming pool—are seven rooms and suites, each named for a local spice (think saffron, nutmeg, and turmeric) and decorated in jewel tones like deep orange and royal purple. All have standard conveniences like hair dryers, toiletries, and air-conditioning as well as complimentary Wi-Fi.

    The hotel’s public spaces are separated into a garden section, featuring trickling fountains and lots of flowers, and an oasis section, which houses the pool and a traditional steam hammam. The riad also enjoys a higher position than its neighboring buildings, resulting in particularly great views from the rooftop terrace. Here, you can take in the Atlas Mountains from the plush lounge chairs (each topped with a straw hat for extra sun protection), the fireplace, or the romantic dining tables, where you can enjoy cocktails or a candlelit dinner. Adding to its private home feel, Riad l’Orangeraie provides guests with a local cell phone to use while in town. The hotel is also available to rent out in its entirety for the ultimate house party.
  • 15 SE 10th St, Miami, FL 33131, USA
    In Miami’s trendy Mary Brickell Village, Perricone’s Marketplace & Cafe is the kind of place you can just relax in. The indoor/outdoor patio keeps you out of the blazing Florida sun but still provides a romantic ambience. To start, tear into baked Brie cheese wrapped in puff pastry dough brushed with drawn butter and powdered brown sugar. The top is then sprinkled with shaved almonds and sticky apricot jam. The melty cheese combined with the sweet sugar and jam is a perfect introduction to an unforgettable meal. Continue to the bruschetta bread basket, the lobster ravioli in a pink vodka sauce, and the lamb chops seasoned with rosemary and served perfectly pink atop a bed of couscous and steamed asparagus. Other highlights include the salmon in a lemon-butter sauce. For dessert, sample the house cake, a combination of chocolate and hazelnuts. As rich as a brownie, it’s the kind of dessert that you want to savor and pairs nicely with vanilla bean gelato. There’s an awesome Italian market in the lobby to stock up on pesto, seafood dip, and plenty of to-go truffles. Be sure to try the peanut butter teardrop.
  • Piazza di Santa Croce, 50122 Firenze FI, Italy
    Standing in the Piazza Santa Croce, a statue of Dante looms over the square from the corner. Florence, where Durante degli Alighieri’s journey through hell, purgatory, and paradise was to begin but not end. In 1829 a tomb was built for him in the Basilica of Santa Croce—the largest Franciscan church in the world. The tomb has remained empty ever since as Dante’s body lies in Ravenna.
  • Street 11
    Travelers incorrectly believe that the street food sold at stalls around Pub Street in the Old Market quarter is authentic. It’s not—not the fruit shake sellers, nor the Nutella pancakes. There is one exception and that’s the ubiquitous sugar cane juice sellers that you see here as well as at local markets, backstreets, and the riverside every afternoon and evening. Follow your ears. Expect to hear the sound of the long pieces of cane being crunched through the crusher or the sounds of swarms of bees buzzing around. The juice will be served in a plastic cup or plastic bag with a straw. If you struggle with the drink in a plastic bag idea, as many foreigners do, then point to a cup. It’s nearly always served over ice and the ice is nearly always safe, thanks to the French who established ice factories across the country during French colonial rule. However, if you’ve not been in the country long or have a weak stomach, skip the ice, just in case. Sometimes Cambodians will add extra sugar to their drinks. Watch carefully and say no if you see the vendor reaching for some, as it’s sweet enough. It’s a terrific thirst-quencher if you’ve been out in the blazing sun all day – and a fantastic pick-me-up if you’re starting to feel that heat.
  • Praia Castelejo, Portugal
    Each time I visit this beach, I am enchanted anew. These beautiful sands, sea, and cliffs are exotic. I sit on the sand watching swimmers, surfers, boaters, and fishermen. I watch the birds happily flying around. I stare at the brilliant blue sky with its puffy clouds gliding by. And I gape at the huge cliffs that tower over all of us.I collect the rare rocks with white stripes running through the stone that are unique to the area. This is Castelejo Beach on the western coast of Portugal where there are many rugged, wild beaches. From Lagos, you go west to Vila do Bispo and follow the signs to this beach. The road is rugged and narrow and ends just above the beach with a parking lot. Get a good map of the area at your hotel. Hungry? The Castelejo Restaurant is at the top of the path to the beach. This restaurant serves octopus dishes and other fresh seafood. If you are there at sunset you will be lucky enough to see this gorgeous beach bathed in glowing light. Try to visit this beach when in the western Algarve.
  • 1354 Kuhio Highway
    In the heart of old town Kapaa, the Olympic overlooks Main Street with laid-back Hawaiian style. Upstairs in an old building that’s been converted into a collection of ragtag shops, the cafe has a commanding presence. Park and wander along the street to make your way to the stairs leading up to the bar and cafe. No pretense upon arrival. The tables lining the open windows in front are choice for people watching and catching the breeze from the prevailing trades. Late afternoon sun streams in and heats things up but is a welcomed delight. There’s always something cold close by to help with the temperature regulation. The bar is a mix of locals and tourists. Happy hour is a draw from four to six with discounts on drinks and select appetizers. I’m a big fish fan when near the source and the fish tacos at the Olympic take the gold. Dressed with a mango salsa and sides of beans and rice, they use two kinds of fish to keep your tastebuds guessing. There is a good selection of island beers and all the fruity umbrella drinks you can imagine. It’s right on the Kapaa multi-use path, so you can cruise in on your beach bomber for a refreshing break. Staff are friendly and service is casually good. Worth a stop when trolling around Kauai for someplace to take a break from vacation.
  • St John, USVI
    Many islands have laws with steep fines against wearing beach wear when not on the sandy shoreline and while you may have heard of folks going au-naturel on St. Martin, that’s certainly not the norm throughout the region. On St. John, however, things were a little different. About a mile walk from a parking lot on the edge of Cruz Bay along what’s called the Lind Point Trail, through typical island bush and over a hill and down through more bush past a fork (where either choice gets you to the same place) intrepid travelers are rewarded with a tiny strip of sand, only around 25 yards long, unofficially known as the island’s only nude beach: Salomon Beach. I’ve been to this secluded sandy alcove a number of times and without fail the maximum number of sun worshipers was never above four or five. In fact, most times, the beach was deserted. So, for years this is where those with a passion for enjoying nature to the fullest could go to let it all hang out in relative privacy… Until recently. Since my last trip to Salomon Beach back in 2007, there’s been a crackdown on this unofficial naturist haven. Suddenly being a free spirit isn’t so free due to the stiffness of fines—around $110 for those caught with their pants down (so to speak). But, hey, doesn’t mean you can’t press your luck!
  • 3700 Wailea Alanui Dr, Wailea, HI 96753, USA
    Now this is truly a place you never want to leave. The infinity edge pool at the Marriott in Wailea, Maui. The pool reached right out to the Pacific Ocean, and you almost felt as if you were in the ocean itself. Grab an umbrella drink, swim over to the edge, and stay there for a couple hours to take it all in. The wonderful staff will also bring you the freshest fruit you have ever had too. And, as you watch the sun go down on the horizon from this exact spot, you can join the Luau by the beach below...or simply stay here all night.
  • Monte Alegre 149, Valparaíso, Región de Valparaíso, Chile
    Built in the 1920s by a Croatian businessman, Palacio Astoreca underwent two years of refurbishment and restoration before opening its doors as a boutique hotel in 2012. The work was carried out to a meticulous degree, maintaining the original parquet floors, and adding splashes of color with art deco furniture and modern art, including one piece by Switzerland’s Frédéric Clot. The stucco-and-brick mansion rises up from the streets of Chile’s port city, Valparaíso, like a piece of red-and-white confectionary.

    A statement staircase winds up to the 23 rooms, some of which have stand-alone bathtubs. And the basement level is home to a small spa with an open-air, wood-fueled hot tub set alongside a living wall. The reception level and entrance hall open out onto a terrace where lunch, tea, and cocktails are served, allowing guests prime views over the hilly city and Pacific Ocean. There are quiet corners for those seeking a solitary moment, including a library and a piano bar, which comes to life in the evenings with live music.
  • 16641 La Cantera Pkwy, San Antonio, TX 78256, USA
    Following a multi-million-dollar overhaul in 2015, this ranch-style Hill Country resort—which is part of the Destination Hotels collection and less than 20 minutes from the airport—has emerged as a spot where both families and the adults-only crowd feel at home. For the former, there are plenty of places for fun on the 550-acre property, including five pools (one is just for kids, with two water slides and a toddler splash area), an arcade (for ages 13 and up), tennis courts, and miles of scenic trails. The hotel even has a partnership with high-end baby gear label Babiege, which grants guests discounts on crib, stroller, and accessory rentals they might need to enjoy a day out. Meanwhile, grown-ups will appreciate amenities like two championship golf courses, Texas-inspired treatments at the Loma de Vida Spa & Wellness (set on one of the highest points in San Antonio, with views to match), an adults-only pool, and private poolside cabanas (available for a fee), which come stocked with fridges, HDTVs, local snacks, and a personal attendant.

    The 496 guestrooms also cater to a variety of needs. The main rooms and suites feature great views, NEST products, rain showerheads and plush furnishings, while the villas set on the golf course offer plenty of space for families, plus a separate reception, complimentary golf carts, oversized tubs, and their own pool bar, cafe, and market. For those seeking some privacy, there’s SEVEN, a 21-and-over floor with a dedicated concierge, lounge, upgraded bath products, private check-in, and more. As you might expect, the selection of eight restaurants and bars is equally varied, ranging from a grab-and-go market, poolside grill, and casual cantina, to the fine-dining Signature, with menus by James Beard Award-winning chef and San Antonio native Andrew Weismann.
  • 543 Park Ave, Park City, UT 84060, USA
    Located just off Main Street, the Washington School House Hotel eschews Park City’s typical rustic style for a pared-down, flea-market–chic aesthetic. Before being reimagined as a design-oriented inn in 2011, the 1889 building served as a schoolhouse for miners’ children and a dancehall for the local outpost of Veterans of Foreign Wars. Today, the interior is anything but traditional, from the whitewashed living room with 16-foot ceilings to the antique mirror and the white, lacquered antler chandelier. Outside, a heated pool sits on the hillside surrounded by aspens and boulders. There’s also a fire pit, fashioned from a steel Olympic torch from the 2002 Winter Games.

    Each of the guestrooms and suites is unique, though all feature reclaimed wood floors, crystal chandeliers, and tall windows. An artful collection of European antiques and vintage paintings adds a bohemian vibe, while white marble bathrooms offer heated floors, walk-in showers, clawfoot tubs, and period fixtures. Guests can also look forward to plush hooded robes and top-notch toiletries from Molton Brown.
  • Soufriere, St Lucia
    From the moment you touch down on the grounds of the 135-acre working cocoa farm, a stay at the Fond Doux feels like a step back in time. It begins in your suite, one of 15 cottages that have been lovingly restored by owners Lyton and Eroline Lamontagne in the colonial style, with traditional gingerbread trim, four-poster beds, and pastel walls. Though some cottages have private plunge pools, you’ll want to make your way to the cascading main pool, which overlooks a verdant rain-forest glen. If all this sounds a little sleepy, don’t fret: A free shuttle is available to whisk guests to nearby Sugar Beach, and frequently rotating minibuses pass the hotel on their way to restaurants and shops 10 minutes away in Soufrière.
  • 1515 Wilder Avenue
    At first glance the small little market open on Thursday evenings at St. Clements Parish in the Makiki neighborhood of Honolulu does not seem like much to stop for. However, I often took friends there or pointed them in that directions for a dinner where trying local food and some old favorites is as easy as visiting a couple of the food stands. The variety of food is great with Thai food, Hawaiian fare, fish tacos, pies, crepes of all flavors, and fruits and veggies to round out a healthy meal. The people are friendly, tables are set up to enjoy your food there or you can take it home for later. Either way, the Makiki market is an great option to easily grab dinner on a Thursday evening. Open Thursdays 4:30-7:30pm