This California city was long considered just a sleepy neighbor of Los Angeles. Now a flourishing wine culture and an infusion of luxe resorts — not to mention the arrival of top-wattage celebrities — have upped Santa Barbara's glam quotient.

Stearns Wharf, Santa Barbara, California
Santa Barbara's Stearns Wharf, as seen from the Hotel Californian.
| Credit: Oriana Koren

"I think that's Oprah's boat."

I rubbernecked on my paddleboard. The Liquid Paper–glossy yacht with blacked-out windows certainly looked like it could be owned by the most famous billionaire in Santa Barbara — or, more precisely, in neighboring Montecito, where Oprah has a 42-acre estate she calls the Promised Land.

I was following Johnny Gill, an instructor from the sailing center, through Santa Barbara Harbor, a serene parking lot for six-figure boats. The jagged peaks of the Santa Ynez Mountains framed the 100-foot masts as they rocked and flickered in the sun, bright as birthday candles. According to Johnny, the harbor has about 1,100 slips, which can go for as much as $20,000 a year.

Johnny is in his late twenties, with an eight-pack that ripples beneath his polo like speed bumps. He moved to Santa Barbara for college and never left, a common story around town. "I'm here for the life," he said as he paddled. "The lifestyle." He glided through the diffuse light, standing gallantly astride his paddleboard like Aladdin on his carpet. Over his shoulder, he called: "Kevin Costner's!"

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What had begun as Santa Barbaran cardio had become a de facto star-maps tour. The Spanish-tiled beach town has become a sanctuary for day-trading oenophiles, ambitious tech-preneurs, and omnipotent media moguls, as well as the truly famous: not since the early 1900s, when more than a thousand silent films were shot at the legendary Flying A Studios, have so many movie stars called Santa Barbara home. Natalie Portman, Jeff Bridges, and Ellen DeGeneres all have houses here; Gwyneth Paltrow, who shot her new Netflix series, "The Politician," in town, is building one.

"Ashton and Mila's!"

At the end of Stearns Wharf, I paused to take in the scenery. In the mountains above Santa Barbara I could see Inspiration Point, a hiking area overlooking the Riviera neighborhood, where the hotel El Encanto (now a Belmond) once housed the silent stars working at Flying A. Below Riviera: State Street, the picturesque Santa Barbara County Courthouse, the Granada Theatre, and the palm trees flanking Cabrillo Boulevard and East Beach. To the east was the ritzy enclave of Montecito, home to San Ysidro Ranch, the five-star-resort setting of A-list nuptials through the decades, from Laurence Olivier and Vivien Leigh to Gwyneth Paltrow and Chris Martin — not to mention JFK and Jackie's honeymoon in 1953. In June, Katherine Schwarzenegger, granddaughter of JFK's sister Eunice, married Chris Pratt there. The ceremony took place just months after the resort reopened following the devastating mudslides that struck Montecito early last year.

A man in his late fifties with a Patek Philippe on his wrist and a French bulldog on his board paddled past. Then, about three feet away, a sea lion torpedoed out of the water and landed with a splat on the dock. I fell to my knees on my board, in a defensive crouch or prayer, or both.

"That was sooo Santa Barbara," Johnny said, laughing as I wobbled back up. I didn't know if he was talking about the guy with the dog, the X Games–ready sea lion, or the out-of-towner struggling to keep up with it all. The sea lion sighed and rolled over to nap in the sun.

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For many years, Santa Barbara suffered from a kind of middle-child syndrome. Among southern California's weekend getaway spots, this manicured town two hours north of Los Angeles lacked the Old Hollywood Midcentury ta-da! of Palm Springs, or the New Hollywood woke-glam of Malibu. Santa Barbara was dutiful, in its spirit (it became a bastion of environmentalism after a 1969 oil spill), in its food (Julia Child frequented its beloved farmers' market), and in its terry-cloth caftan selection. Patrolled by a code-enforcing organization known as the Santa Barbara Architectural Board of Review, it was a very "I'll have the scallops" kind of place.

Guide to Santa Barbara
From left: Satellite, part of a three-story co-working space; the pool at San Ysidro Ranch.
| Credit: Oriana Koren

Then along came "Sideways," the 2004 Alexander Payne movie that followed a boozy foursome through the vineyards and tasting rooms of Santa Barbara County. Its influence around town, 15 years later, is still enormous. Rajat Parr, a 47-year-old winemaker and sommelier known for his Sandhi line of organic Pinot Noirs and Chardonnays, told me, "It's something we can't get away from. Why would we?"

In 2006, a group of local vintners sought to capitalize on "Sideways" by establishing the Urban Wine Trail, a collection of 33 tasting rooms featuring area wines. There are quirky shacks like Municipal Winemakers, with vintage oil portraits on the walls; formal, dark-wood-paneled presentations from vineyards like Margerum; secluded, Italian Brutalist warehouses open by appointment only, like Sanguis; even an unofficial yet delicious stop: a cupcake stand with two daily wine-infused offerings in the Santa Barbara Public Market.

One of Parr's favorite spots is Satellite, a downtown bar with regional natural wines, lime-velvet Midcentury seating, and a guest magician on Thursday nights. It's in the lobby of a three-story co-working space called the Impact Hub. When I dropped by on a Friday, it was packed with lunchtime laptoppers in nerdy frames and sneakers from local brand SeaVees. I ordered a house-made shrub and vegan tacos with shiitake mushrooms and chatted with a guy enjoying a glass of Parr's Domaine de la Côte Pure Pinot Noir. He turned out to be Parr's business partner, Alejandro Medina, co-owner of the a celebrated Bibi Ji, a SoCal Indian boîte down the street.

"Santa Barbara was a little, I guess, serious when I was growing up here," he told me. He left to work in Los Angeles before coming back a few years ago to run the wine program at the Spanish restaurant Loquita. "I feel like now this city is finally bridging the gaps — connecting our food and culture to the landscape." He mentioned the number of stores and restaurants, including Satellite, that offer classes.

The shopping has gotten better, too, he added. I'd heard about the handmade denim at Ace Rivington, which also makes the $28 Aviator beanie, an essential part of the local Chilly Morning Uniform. Founded by Beau Lawrence, a former Guess jeans exec, the shop has popular (and often sold-out) Italian-milled, California-made jeans, the PT17, which are sold for $300.

What to Do in Santa Barbara, California
From left: Paddleboarding in Santa Barbara Harbor; clothing designer Catherine Gee at her boutique in Laguna.
| Credit: Oriana Koren

I got on the waiting list, then walked past Amazon's new offices and a guy texting while unicycling, toward the Presidio, where the last of the Spanish fortresses were built when this region was still known as Alta California. There, near the 19th-century adobe residence of the commandant of the Presidio de Santa Barbara, I found Kotuku Elixir Bar, where I ordered an Expansive Qi tonic, made with Eucommia herb, Chinese mountain ant, ginseng, and dragon tea. The Australian owner, Olly Lithgow, is a reliable wizard and potion maker for the keto/paleo/Whole 30-ing dignitaries who visit each winter for the Santa Barbara International Film Festival. (Popular among the stars: an adaptogen made with lion's mane mushroom, said to help with anxiety.)

Down the street, I found Make Smith, a third-generation leather-goods company that sells vegetable-dyed cattlehide satchels. Filled with raw-wood sawhorse tables and the fragrance of freshly tanned leather, it felt more like a workshop than a boutique. I heard machinery in the back and peered through a doorway. Owner Steven Soria was carefully feeding a tote bag through a thick-needled sewing machine. "He makes them one at a time," a sales associate whispered. "Come back and take a class!"

A few blocks from the beach, I grabbed an excellent cup of coffee at Breakfast Culture Club with surfers and their admirers. The talk — over PB&Js made with spicy peanut butter and brioche as thick as a paperback — was of the diminishing number of public benches in downtown Santa Barbara. The city has been removing them in what appears to be a strategy for discouraging its rising homeless population.

"Santa Barbara isn't always perfect," Catherine Gee acknowledged over a glass of Chardonnay after I checked in to the Ritz-Carlton Bacara, a secluded, expansive property just outside of town. The 35-year-old designer is known for 90s-throwback slip dresses of the sort last seen when Gwyneth and Winona were still friends. As we watched the sun set over the largest undeveloped stretch of coastline in southern California, she tried to explain why so many young people are moving to town. "We are in this wellness era," she said. "Quality of life is becoming more important than where you're living it. For me, Los Angeles is close enough to get to for my work, but life is just better here. Even if it's getting expensive."

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The next day I stayed at the Hotel Californian, a collection of Spanish-colonial structures that opened in fall 2017 on a site near the beach where a property of the same name was destroyed in the earthquake of 1925. The interiors, concocted by Martyn Lawrence Bullard, Cher's and Kylie Jenner's decorator, are a wonderfully noisy mix: Moroccan light fixtures, louche 70s seating, op-art pillows. There's a rooftop pool, Pacific views, and a low-lit restaurant called Blackbird where I had uni on avocado toast. It's a short walk from the train station, making it popular with the always-important visiting-from-Hollywood crowd. As I set my bags down, the Amtrak Pacific Surfliner pulled into town with a long honk and a haul of weekending Angelenos.

Downtown Santa Barbara
A skateboarder in downtown Santa Barbara.
| Credit: Oriana Koren

Outside, I inhaled the scent of star jasmine and salt air before dodging a fleet of roll-aboards trailing visitors in wedge espadrilles and broad, floppy hats. My North Star was a pink, geometrical mural on the side of Galerie Silo, a warehouse turned art gallery in the Funk Zone, the city's new arts district. The 13-block area, formerly a skein of run-down artists' studios and abandoned seafood warehouses, has become a weekend playground for Bachelors and Bachelorettes. Bordered by the train station, Highway 101, the Hotel Californian, and East Beach, it has tasting rooms, art galleries, shops like the Channel Islands Surfboards flagship, and an Epcot of dining options from Acme Hospitality, owned by Sherry Villanueva, a former trend forecaster for Target. For Spanish food there's Loquita, where hirsute, leather-aproned butchers slice Ibérico de Bellota as thin as Communion wafers. For Italian, Lucky Penny pizzeria. For Southern, Helena Avenue Bakery. For Vietnamese, Tyger Tyger, where Julia Louis-Dreyfus, who has a place on the beach near the new Rosewood hotel, is an investor.

That night I headed downtown to Bibi Ji, which was filled with locals bathed in pink neon light. Over a dinner of crunchy, creamy uni biryani — fried rice served in a sea urchin shell — I watched Medina greet friends and new friends with a two-step bro handshake/hug. He had the energy of a marketer and the warmth of a local boy done good.

"Where are you going tomorrow?" he asked. Montecito, I told him.

"It's a different world over there," he said.

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In 1984, a daytime soap premiered on NBC. For nine years, "Santa Barbara" chronicled lives, loves, earthquakes, and sundry acts of sailboat sabotage. But although it briefly starred a young Leonardo DiCaprio and later became the longest-running series ever to air on Russian television, it failed to indelibly imprint the city into the American consciousness the way, say, "Dallas" did for Dallas, or "Nashville" for Nashville, or "The Hills" for Los Angeles. I was thinking about "Santa Barbara" as I watched DiCaprio stroll through the lobby of the Rosewood Miramar Beach. The new property in Montecito — two interstate exits and a rip through the space-time continuum from State Street — is as photogenic and heart-eyes-emoji as its poolside frosé. It had just opened to great fanfare on the grounds of Miramar by the Sea, a legendary resort that served wealthy Montecitans for more than a century.

The hotel is backed by the real estate magnate Rick Caruso, best known for the Grove, the upscale outdoor shopping mall in L.A.'s Fairfax District. He hired Rosewood to manage the property, the Santa Barbara area's first hotel on the beach. To be clear, one must cross the Amtrak tracks — with the assistance of a dark-suited security guy — to reach the waterfront from the main building.

The rooms are stocked with Goop dietary supplements. The gift shop, called Goop Sundries, is Gwyneth's first hospitality venture. Guests can purchase sandals, $3,600 necklaces, and kaftans — yes, with a k — rendered in silk voile. The hotel is also home to Caruso's, a navy-lacquered Italian restaurant inspired by Caruso's 215-foot yacht, Invictus.

After I checked in, I walked over to the grand piano, which faced a vast lawn dotted with white cottages like golf tees. A small gray-haired woman in a black vest was playing a down-tempo arrangement of Maroon 5's "Girls Like You." Nearby, a blond man was filming a blond woman with his iPhone. "Hi, I'm Heidi," the woman said to me, or maybe to the room, or maybe to the camera held by her husband, Spencer Pratt.

Rosewood Miramar Beach hotel in Santa Barbara
Private bungalows at the new Rosewood Miramar Beach hotel, in Montecito.
| Credit: Oriana Koren

Besides the Rosewood, Montecito has the revamped San Ysidro Ranch, where guests can stay at Kennedy Cottage, where the eponymous president and first lady honeymooned, or the Warner Cottage, named after the owner, Beanie Babies magnate Ty Warner. He also owns the Four Seasons Resort The Biltmore, where, in July, the new $12,500-a-night, 4,000-square-foot, butler-attended Ty Warner Villa was unveiled. Beanie Babies are sold in the gift shops of both properties.

Officially, Montecito is an unincorporated Santa Barbara neighborhood, but residents speak of it as a World Apart. On Saturday nights, Oliver's is its capital. The haute vegan spot — think $18 farro Bolognese with cashew butter, "crab" cakes, and kombucha on tap — has the pale-wood infrastructure of East Hampton, but the pedicured toenails and logoed handbags of Beverly Hills. It is one of several spots along Coast Village Road, Montecito's main drag, that have dog-friendly patios and Maserati-friendly valet parking. There's also Lucky's Steakhouse, owned by Gene Montesano, cofounder of the circa-Y2K denim company Lucky Brand Jeans, and frequented by Carol Burnett, Rob Lowe, and Ellen.

Then there's the Silver Bough, one of two restaurants at the Montecito Inn (the other is the Monarch) run by former "Top Chef" contestant Phillip Frankland Lee and his wife, Margarita Kallas-Lee. It serves what is currently the most expensive meal in California, a $550-per-seat, 18-course experience, narrated by a Greek chorus of sous-chefs who serve King pigeon breast, "super venison," olive-fed-Wagyu rib eye, and smoked-vanilla mousse on custom Michael Aram stoneware.

Following the third dessert course — chamomile brûlée — a couple I'd dined with offered me a ride back to my hotel. From the front seat of their Bugatti, Quentin Wahl, a race-car driver, and Kristin Turner, the owner of a local Pilates studio, told me that how you choose to travel between Santa Barbara and Montecito — the 101 or the back roads of the Riviera, past the Santa Barbara Bowl — says a lot about you. Who needs to rush when you live here?

The next day, I got in my rental car to go back to the airport. I approached the interstate, then thought better of it, heading instead toward San Ysidro Road. I decided to go the long way.

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The Best of Santa Barbara

Where to Stay

Hotel Californian, a cluster of Spanish-colonial-style buildings two blocks from the waterfront, has interiors designed by Martyn Lawrence Bullard and a rooftop pool. The 92 rooms at the Belmond El Encanto are done up in classic California Mission style, while the bungalows at Four Seasons Resort The Biltmore are surrounded by 22 acres of lush gardens and courtyards. At the Ritz-Carlton Bacara, you can unwind on two private beaches and at the expansive spa. In neighboring Montecito, check in to the luxe new Rosewood Miramar Beach — and don't forget to visit its Goop Sundries shop. The 500-acre San Ysidro Ranch is popular with celebrities for weddings as well as getaways.

Where to Eat and Drink

Choose from a long list of natural wines at Satellite in the Funk Zone, then sample the offerings at Bibi Ji, a well-loved Indian wine bar down the street. Loquita has a stellar menu of Spanish wines, tapas, and paellas. At Kotuku Elixir Bar, order from a roster of healing elixirs and smoothies. Oliver's, an haute vegan restaurant in Montecito, offers appealing produce-forward entrées and kombucha on tap. Find a more elevated scene at the intimate, high-concept Silver Bough at the Montecito Inn .

Where to Shop

Pick up premium denim at Ace Rivington downtown, or opt for a handmade tote from Make Smith, a family-owned leather-goods shop. Breakfast Culture Club has more than breakfast, with great hoodies, T-shirts, and art. Catherine Gee designs and sells silk dresses and camisoles at her Laguna boutique.

A version of this story first appeared in the November 2019 issue of Travel + Leisure under the headline Southern Exposure.