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The front section of this small spot was crowded with locals having a quick drink and a plate of cicchetti. We had reserved one of the six tables in the back. The menu, written on a blackboard, was all almost all unknown to me. Thankfully my Milanese traveling partners were there to translate. We ordered plates of baccala manecato and polenta, a Venetian style fish lasagna, and a seafood pasta. All washed down with jugs of a cold local white.

It makes sense that the California cool of James Perse’s clothing and accessories for men and women has made its way to Cabo, where its sold at one of several shops that opened on the property of Flora Farms in late 2015. Whether you forgot to pack for the coastal climate of Baja or you just want to expand your wardrobe, attentive staff can help you add a few items to your style repertoire.

The Waldorf Astoria Los Cabos Pedregal is a majestic resort that sits at the spot where the Pacific Ocean and the Sea of Cortéz meet. All 119 rooms have an ocean view, complete with binoculars for whale-watching, as well as a private plunge pool, a fireplace, a rain shower, and a welcome bottle of Clase Azul tequila. Decorative accents include tasteful local art, such as hand-embroidered pillows, ceramic sculptures, and hand-forged metal light fixtures. On the service side, every guest is assigned a round-the-clock personal concierge. The relatively small number of rooms keeps the vibe intimate and creates a sense of privacy throughout the property.

La Casa de Don Juan knows how to do breakfast. An instant hit when it opened, the restaurant initially focused entirely on the most important meal of the day with dishes like pancakes, huevos divorciados (two fried eggs, separated on the plate by refried beans), chilaquiles (eggs, scrambled or fried with crisp strips of tortilla and topped with salsa), and several other Mexican favorites. Its café de olla—a traditional cinnamon-sugar coffee—might be the best in all Los Cabos. Everything tastes like the most incredible home cooking, and the space itself more resembles a two-story residence than a traditional restaurant. The menu and hours have now extended to include lunch. Opt for the prix fixe menu or à la carte on taquitos (rolled tacos), cochinita pibil (slow-roasted pork), or chile relleno (a poblano chile stuffed with cheese and then batter fried).

The San Francisco Proper Hotel is the hottest new hotel in town. The reason why? International grande dame of maximalism, designer Kelly Wearstler, revamped a down-and-out tourist hotel deep in the heart of the city, and established the Proper as a magnet for trendsetting visitors and locals. When guests arrive at the 131-room hotel and step inside the flatiron building, they’re treated to Wearstler’s signature pattern-on-pattern aesthetic. In the ground floor lobby, Wearstler sets the mood with salon-style seating areas using richly reupholstered vintage furnishings and Cubism-inspired paintings. Michael Adams, formerly of Central Kitchen, oversees the hotel’s main restaurant, Villon. And while the Proper isn’t the place for those looking for a Zen retreat, it is the place to order a Fifi the Flea cocktail (Tequila Ocho Plata, Ancho Reyes, Ancho Reyes Verde, grapefruit, honey, vanilla, lime, smoked salt) at Charmaine’s, the stylish rooftop bar. Between the fire pits and the bird’s-eye view of Market Street all the way to the bay, it’s no wonder the Proper has become the destination to see and be seen.

At the entrance of Lake Izabal stands a stone citadel. Built in the mid-1600s by the Spanish, the imposing structure thwarted thieving pirates from attacking the lake, which was used as a storage facility for transport goods. El Castillo de San Felipe later served as a prison. There are cannons and weapons along with sweeping natural vistas. The site is also home to myriad wildlife, including a variety of monkeys.

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….”

The mysterious rooftop of Casa Mila both charms and haunts visitors. The glorious October sky above frames the organic forms, each sculpted face watching as I creep up and down the rolling ramps. Children can’t resist playing here, and fortunately there are now fences all around. In my mind, I erase all of those pesky safety features to envision the smooth sculptures growing towards the sky from a scrolling sandy field. Once a site for a scene from Star Wars, the rooftop is now a destination for lovers of Barcelona and Antoni Guadi’s “Modernisma” style. When you visit, you’ll learn the secret behind those long vertical faces rising up above the mystical rooftop.

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.

“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.

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).

Wouldn’t pulling a brightly painted ceramic bowl or tile out of your bag at home summon a vivid memory of this sunny corner of Spain? Santa Ana has been selling the hand-painted work of local ceramic workshops since 1870 and offers a wide variety of items from small eggcups to large tile murals.

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.

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.

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.