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  • If the romance of a vineyard sounds appealing, several wineries offer you the chance to dine among the vines. Locals choose the Vega Manchón Winery (pictured here), where former Rosewood chef Carlos Segura pairs entrées with the vineyard’s wines. Restaurante de la Santísima Trinidad, nestled within the grounds of its namesake vineyard, is open only on weekends but can provide a relaxing daylong respite, especially if combined with the winery’s other diversions like polo matches (and polo lessons for all levels of expertise), yoga, or massages. For best romantic results, follow the recipe of poet Omar Khayyam, “A jug of wine, a loaf of bread, and thou….”
  • Piazza Bellini, 1, 90133 Palermo PA, Italy
    The church of San Cataldo and its neighbor, La Martorana, both overlook the Piazza Bellini but offer contrasting experiences. San Cataldo is modest on the outside, and its interior remains unfinished more than 850 years after its construction—but it is no less beautiful for that. La Martorana (also known as Santa Maria dell’Ammiraglio), on the other hand, is one of Palermo’s greatest remaining churches from the Middle Ages. The elaborate mosaics that decorate its interior are thought to have been created by the same artisans who created the Palatine Chapel.
  • 4515 S Congress Ave, Austin, TX 78745, USA
    “Everyone from the late blues musician Stevie Ray Vaughan to the Butthole Surfers has played at the Continental Club. Musicians who do big gigs in Austin like to play small shows here afterward,” says Liz Lambert.
  • Liberty Station, San Diego, CA, USA
    Built in the 1920s, San Diego’s onetime Naval Training Center began its transformation into a cultural and retail space in 2000, when the city bought this massive Spanish colonial revival complex to house galleries and shops as well as concert, movie, and lecture venues. The shopping is largely culinary here, with food hall–style purveyors of everything from coffee to pasta (don’t miss the vinegar tasting station at Baker & Olive). But there are also local accessory shops worth visiting: Down a small, out-of-the-way corridor, you’ll find the only wholesale outlet of Double Happiness Jewelry & Home. This San Diego–based producer of handmade, one-of-a-kind pieces is a favorite of celebrities (Oprah, Cindy Crawford, and Blake Lively, to name a few). The jewel-encrusted hoop earrings are especially hard to resist. Other Liberty Station accessories worth checking out: the rotating assortment of local home goods and accessories at Moniker General (look for Norden Goods candles and Bradley Mountain bags).
  • km 6, México 1 1, Misiones del, 23455 Cabo San Lucas, B.C.S., Mexico
    Sunset Monalisa is one of the most romantic restaurants in the world. Its views of Cabo San Lucas Bay and the arch at Land’s End are spectacular any time of day but particularly at sunset, when the sky turns vibrant shades of red, yellow, and purple. Love is definitely in the air here: Servers report at least one engagement per week, and it’s a favorite wedding venue. The multitiered cliffside restaurant features a Taittinger Terrace Oyster and Champagne Bar, as well as an exceptional Mediterranean menu from chef Paolo della Corte, who trained in Michelin-starred kitchens. Navigate the à la carte options independently or opt for the prix fixe or tasting menus.
  • 540 Jackson St, San Francisco, CA 94133, USA
    Fly fishing may not be top of mind while walking through San Francisco’s Financial District, but fantasies of casting in crystal clear rivers and commencing the day around a campfire are sure to materialize once you step inside Lost Coast Outfitters. The upscale sporting goods store specializes in top-of-the-line fly fishing gear, but shop owner George Revel has an eye for provisions that tug at the inner outdoorsman in all of us, such as indestructible Yeti coolers, leather-trimmed duffle bags from Filson, and classic Simms flannels in timeless red-and-black check. The grand historic Beaux Arts building only adds to the appeal, as does the 300-plus-bottle whiskey collection hidden behind a wall of waders and waterproof booties. Pro tip: Inquire about joining the exclusive Tin Cup Society to gain access to speakers, casting clinics, expeditions, and curated gear packages.
  • 112 Academy Dr, Austin, TX 78704, USA
    A compound-like hideaway on a leafy street a block from trendy South Congress Avenue, Hotel Saint Cecilia is a retro-glam love letter to the 1960s and ‘70s rock music scene, named for the patron saint of music and poetry. But that doesn’t mean that rock stars smash guitars and throw ragers here (unless they rent out all 14 rooms, of course); unlike at its nearby sister properties, Hotel San José and Austin Motel, only guests and club members are welcome at the lounge, a laid-back affair with a Parisian-café–style patio, chesterfield sofas and a fireplace indoors, and craft cocktails and gourmet small plates. Between the 1888 Victorian main house—originally inhabited by a descendent of Davy Crockett—and verdant grounds that hide private porches and a serene pool, the hotel feels more like an impossibly stylish artists’ retreat than a celebrity getaway.

    Each distinctively decorated room is larger than many an apartment, and seems ripped from the pages of a fashion magazine photoshoot. Every detail has been thought through, from the refreshing Grown Alchemist body care products to the Swedish Hästens mattresses (the hotel is the only one in North America with them in all rooms) to the impressive library of LPs to borrow. Everyone’s a rock star, here.
  • 500 Avenue N, San Francisco, CA 94130, USA
    Along with a great view of San Francisco, Treasure Island is home to a popular flea market, formerly Treasure Island Flea, and now called TreasureFest. Each month around 400 curated vendors set up and peddle their wares. Stalls offer antiques, originally designed art and clothing, and vintage curiosities. You will also find about two dozen food trucks, live music, kids’ games and activities, and some local wine sellers to fuel your shopping fire. The two-day flea market takes place the last weekend of every month. Launched in 2011 to support local artists and entrepreneurs, Treasure Island Flea is now a must-do Bay Area event.
  • For an amazing three-day tropical escape from NYC, look no further than San Juan, PR. A clean, comfortable, and affordable option within striking distance of the airport (no car rental required) is the Marriott Isla Verde. Great long board/SUP surf break right off the beach, quick access to Old San Juan, and a relaxed vibe make for a family/couple-friendly escape from NYC. Stay a half-mile down the beach at the Ritz Carlton for the full poolbar/glam scene or just pop in there for a great lunch. Either way, this is a gorgeous stretch of beach with easy and close access to any major airport in the continental US and a great place to get away, without any passport or other hassles.
  • Nørre Farimagsgade 41, 1364 København, Denmark
    This place is an interesting blend. In the recent Danish tradition, it is a partnership between a number of different creative types. This time, those personalities happen to be design-oriented people from the food, interior design, and dinnerware design communities. This restaurant has focused completely on providing a rich, intensely rustic experience that embodies modern trends in both the New Nordic cuisine movement and Danish design. Recent offerings include flounder with fried chicken skin and sauce made from fermented asparagus and grilled lobster with juniper pancake and pointed cabbage. Photo: Höst.
  • Gobernador Rafael Rebollar 94, San Miguel Chapultepec I Secc, 11850 Ciudad de México, CDMX, Mexico
    Three friends who found themselves thrown together in the New York of the 1990s—artist Gabriel Orozco, who has been featured at MoMA, the Pompidou Center, and the Tate Modern; Mónica Manzutto, who worked at the Marian Goodman Gallery; and José Kuri, who was completing an M.A. at Columbia—originally came up with the idea for what is now arguably Mexico’s most influential gallery. Kurimanzutto began with some ephemeral Colonia Roma events, often in nontraditional spaces. Today the gallery occupies a structure commissioned from renowned architect Alberto Kalach; its stable of artists includes Mexican creators of international stature like Dr. Lakra, Miguel Calderón, Carlos Amorales, and Damián Ortega, as well as global talents like Akram Zaatari, Apichatpong Weerasethakul, Anri Sala, Danh Vo, Jimmie Durham, Rirkrit Tiravanija, and Monika Sosnowska. Kurimanzutto’s shows—not to mention the openings—mark the pulse of the Mexico City arts scene.
  • 4048 Sonoma Hwy, Napa, CA 94559, USA
    When you tell your friends that you’re headed here, everyone will chime in about the dish that you have to get. ‘Make sure you try the smoked salmon flatbread!’ ‘The burger, be sure to get the burger’.’ ‘The donuts! You have to get the donuts!’ It’s good to know that with breakfast, brunch or lunch, they don’t take reservations. Be prepared to possibly wait and hang out on the porch swings or hang out at the bocce courts and play a while (they’re about a 10-minute walk from Boon Fly). With dinner, they do take reservations and I’d encourage you to get those well-ahead. If you’ve had a big bike ride in nearby Napa Valley or are headed in to downtown Napa for a concert or event, Boon Fly Cafe is just 5 miles away and will leave you with your belly full and happy.
  • San José del Cabo 1227, centro, Centro, 23400 San José del Cabo, B.C.S., Mexico
    Cabo’s first-ever microbrewery, Baja Brewing Co. has a cantina located on the rooftop terrace of Cabo Villas Beach Resort & Spa. Take in views of Land’s End with a pint of the flagship Cabotella blonde ale and a wood-fired pizza made with beer yeast dough.
  • 1 Collins Diboll Cir, New Orleans, LA 70124, USA
    This is the oldest and grandest art institute in a city that’s long captivated artists. The Neoclassical building sits amid the greenery of massive City Park (conveniently at the end of the Canal Streetcar Line). It’s an especially good destination for admirers of Edgar Degas, who spent an extended vacation in New Orleans visiting relatives in 1872; a number of his works are displayed here. Just outside the museum is the beautifully landscaped and well-curated five-acre Sydney and Walda Besthoff Sculpture Garden, which perfectly melds the old and new. Some 60 sculptures are arrayed amid reflecting lagoons and 200-year-old live oaks.
  • 67710 San Antonio Street
    Some people dream of private islands with snowy sand and palm trees. Others fantasize about sleeping in a John Lautner house. For the latter, nothing beats this remote 1947 compound of luxury “living units” designed by the Frank Lloyd Wright protégé, the only Lautner residence open to public bookings. All concrete, redwood, glass, and steel, the four flats, which sleep two adults each, are distinctly designed with vintage furniture, organic cotton pillow-top mattresses, Heath Ceramics–tiled showers, and contemporary kitchens. Spend the day sunbathing from your private patio and cooling off in the saline plunge pool, and stargaze from the skylight above your bed at night. The micro-resort is self-catering, but that makes it all the more special—instead of eating in a restaurant, up to 12 people can dine under a communal redwood pergola; arrangements can be made for private chef dinners there, too. A hidden speakeasy-inspired bar for guests of the Ranch House (this additional accommodation, not a Lautner, sleeps four) only fuels the retro fantasy. Plan ahead: Weekends fill up months in advance.