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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.

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 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.

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.

In a city known for its breakfast tacos, it can be hard to decide where to start your day. One place that will never disappoint, however, is La Villita Cafe. The options here are simple—think bean and cheese, potato and egg, and chorizo and egg—but everything is delicious, especially the brisket and egg taco. When you’re done eating, check out the neighboring La Villita art community, which provides a window into San Antonio’s diverse past.

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.

Opened by local restaurateur Lisa Wong in 1992, Rosario’s started as a neighborhood café, where San Antonio residents came to satisfy their Tex-Mex cravings. Today, it’s a city institution, known for its south-of-the-border specialties and house favorites. Don’t miss the tantalizing albondigas con arroz (Mexican meatballs braised in a spicy broth and served with rice and queso fresco), or the flavorful enchiladas Mexicanas (three queso-filled enchiladas smothered in a fragrant chile-infused sauce). And be sure to wash it all down with a perfectly crafted margarita.

In 1977, University of Texas marketing major Chris Madrid opened a small burger and taco joint with help from his family and friends. Today, his eponymous restaurant is one of San Antonio’s best spots to grab a quick bite. Burgers are the way to go here. Choose from menu favorites such as the Cheddar Cheezy (melted cheddar cheese, mustard, lettuce, tomato, and pickles), the Tostada (refried beans, chips, onions, and cheddar cheese), and the Porky’s Delight (bacon and melted cheddar cheese), and be sure to get a side of nachos or chalupas.

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.