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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).

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.

What was in the mid-20th-century just an inexpensive area to build warehouses and showrooms along the Trinity River has evolved into a vibrant live/work community that’s home to noted restaurants, trendy hangouts, upscale apartment buildings, and—true to its name—a wide array of design-focused businesses. Whether you’re in the market for a French impressionist painting or an edgy installation, the galleries along Dragon Street have got you covered, while Slocum Street is the place for antiques, decorative pieces, and midcentury furnishings, and Howell Street is a treasure trove of vintage and thrift shops. Enjoy an upscale meal at Oak, a beer at the Meddlesome Moth or Texas Ale Project, a cold treat at Pop Star Handcrafted Popsicles, or a cooking class–meets–dinner party at The Cookery. Keep an eye out for Eagles co-founder Don Henley, who built a private recording studio in the area.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Wine aficionados set their sights on the Guanajuato Wine Route, now perhaps second only in Mexico to the trails in Baja California’s long-established Valle de Guadalupe. While wineries have existed in this region for several decades, San Miguel only recently received official designation as a wine route, thanks to wineries like Vega Manchón (owner Ricardo hails from Mexico City); Bodega Dos Búhos, where art by Peter Leventhal mesmerizes visitors almost as much as the wine; or Vinícola Toyán. Newcomer labels like Santísima Trinidad have joined the old-timers in hosting vendimia events every weekend in August, with Santísima adding extra attractions like polo games and olive-oil demonstrations. No going Sideways for oenophiles here; they will head home with a new wine destination secret—and a bottle or two.

An active parish of the Roman Catholic Diocese of San Diego, Mission Basilica San Diego de Alcalá remains a tranquil place of worship and reflection. Regardless of your religious beliefs, the first of California’s 21 missions is well worth a visit for its extensive history. It was originally constructed in Presidio Park in 1769 but moved inland to its current site just five years later. Records show that it was the first place in California to cultivate olives; tree cuttings from this mission would later be used to found olive groves at other missions around the state. It’s also home to the grave of Father Luis Jayme, the state’s first Catholic martyr; he was killed when American Indians stormed the mission in 1775 and is now buried next to the altar. Destroyed many times over, the mission was most recently rebuilt in the 1930s, but looks as it would have in the early 1800s.

The work of septuagenarian silversmith Juan Carlos Pallarols has earned him an international following. (Recently, the artist crafted a papal chalice for his friend Francis.) Visit the studio/showroom in the modest San Telmo neighborhood to see and perhaps purchase some of his complex, finely wrought pieces. A set of silver-handled steak knives makes a great souvenir.