A Classic Hollywood-Inspired Luxury Road Trip Through Southern California

Courtesy Hotel del Coronado

Get ready to time travel—in serious style.

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There’s a certain undeniable and irresistible glamour about Hollywood’s Golden Age—from the birth of silent film to the rise (and fall) of the studio system and from Charlie Chaplin and Clara Bow to Humphrey Bogart and Marilyn Monroe. For more than half a century, Hollywood’s magic loomed large, even as the country faced two World Wars, a Depression, and countless cultural and political shifts, and the legacy of this era has lived on well beyond its heyday. As the center of all things Hollywood from the 1910s onward, Los Angeles was undeniably the home of the Golden Age, but it was hardly the only town to be graced by its charms. Whether sites for filming the next big movie or havens for stars in need of an escape, many of Southern California’s cities played a sizable role in the landscape of Old Hollywood history, and there’s no better way to experience the Golden Age legacy than with a luxury road trip through the region. Below, we’ve mapped out the perfect route, from Santa Barbara to San Diego, stopping at the most star-studded spots along the way. 

Santa Barbara


Peter Malinowski/InSite/Courtesy San Ysidro Ranch

Start your trip an hour north of Los Angeles in beautiful Santa Barbara, a favorite destination among Old Hollywood’s biggest stars and starlets. The coastal town has long been known for its understated elegance and ample privacy, which offered celebrities a welcomed reprieve from the bright lights of Tinseltown. 

Related: How Orange County Became the Trendiest Beach Destination in California


Courtesy Four Seasons The Biltmore

Follow in the footsteps of Bing Crosby, Greta Garbo, and Gregory Peck, and stay at the gorgeous Four Seasons The Biltmore, an American Express Fine Hotels & Resorts property and a mainstay of the area since 1927. A virtual who’s who of Hollywood during its Golden Age, the hotel is set among 22 acres and is dotted with lush gardens and secluded courtyards, fountains, and red-brick pathways, and Spanish-style villas and bungalows that are rich with the casual glamour guests like Lana Turner and Errol Flynn came to know and love. And although the Biltmore’s strict dress code and secret poker room may have since gone the way of Hollywood’s defunct studio system, photographs of the hotel’s star-studded history remain today, thanks to the official resort photographer, who captured everyone from Rock Hudson to Ronald Reagan. For those in search of a more intimate stay, head to the romantic San Ysidro Ranch, where John and Jackie Kennedy spent their honeymoon and Laurence Olivier and Vivian Leigh quietly tied the knot.  


Barbara Kraft/Courtesy Four Seasons The Biltmore

When you’re not busy soaking up the sun at Butterfly Beach, catch a match at the Santa Barbara Polo & Racquet Club, which attracted the likes of Spencer Tracy, Walt Disney, and producer Darryl Zanuck and where bombshell Jayne Mansfield once presented winners with their trophies. Grab a bite at El Paseo Restaurant, a Mexican eatery that was patronized Ginger Rogers and Fred Astaire, Rita Hayworth, Shirley Temple, and Katherine Hepburn, to name but a few.


Courtesy Ganna Walska Lotusland

Finally, finish your afternoon with a trip to Ganna Walska Lotusland, an expansive 37-acre estate that’s home to one of the best botanical gardens in the world. Lotusland’s late owner, Madame Ganna Walska, was a well-known opera singer and socialite, and during her more than four decades on the property, she played hostess to Dame Judith Anderson, Gloria Swanson, Cesar Romero, Pola Negri, and many others. 

Los Angeles

Hollywoodland, The City of Angels, Tinseltown, La-La Land—whatever you want to call it, there’s really nothing quite like Los Angeles when it comes to the history of cinema’s golden age. While the stars of Old Hollywood spent their weekends and holidays vacationing in nearby towns, their careers and lives were quite clearly in LA, so there’s no shortage of history-clad spots here. But as eager as you might be to walk in Marlene Dietrich or Marlon Brando’s shoes, don’t fall for the maps of celebrity homes or the Hollywood Walk of Fame; instead, relive the Golden Age in style and visit only the best of the best.


Jason Frank Rothenberg/Courtesy Chateau Marmont

It may seem like every hotel in LA played a role in cinematic history—be it by hosting an awards ceremony or party, calling Hollywood bigwigs guests, or serving as the backdrop to a popular film—but there are only a few whose reputations truly precede them. Chateau Marmont is one such place. Opened in 1929 as an exclusive apartment building, the hillside property was converted to a hotel just two years later, but its residential undercurrent remained, leading many guests to take refuge at the Chateau for months or even years on end. The so-called “Castle on Sunset” has long been a discreet sanctuary for actors, musicians, writers, and artists to let their inhibitions run free away from the public eye. Filmmaker Billy Wilder slept in the bathroom, Desi Arnaz would escape to the hotel whenever he fought with Lucille Ball, Nicholas Ray had an affair with 16-year-old Natalie Wood in the bungalows, Led Zeppelin got kicked out for partying too hard, Bette Davis nearly burned down the hotel on two separate occasions, and John Belushi famously died from an overdose in his Chateau suite. Even these days, you’d be hard pressed to visit the hotel without spotting at least one celebrity, but more than anything, a stay at the Chateau is about paying homage to its expansive and ever-elusive history. For more obvious old-world glamour, head to the American Express Fine Hotels & Resorts property Hotel Bel-Air, a hotspot for Hollywood stars since the 1940s. The 12-acre property has long been a haven for those looking to relax and indulge undisturbed, and as the birthplace of the posh Bel-Air community, the hotel regularly hosted Audrey Hepburn, Grace Kelly, Cary Grant, and Marilyn Monroe when she wasn’t at the nearby Beverly Hills Hotel. Hotel Bel-Air still overflows with Old Hollywood legend, and guests can live like true cinematic royalty in any of its 103 guest suites or in the beloved Presidential Suite, where the Prince of Wales said he slept better than at any other hotel in the world.


Courtesy Hotel Bel-Air

Diving into the deep histories of either of these hotels can very well occupy an entire trip to LA, but if you are able to pull yourself away from their walls and check out some of the city’s other significant spots, be sure to do so in true Golden-Age spirit with the help of a classic car. Get behind the wheel of a 1957 Chevrolet Bel Air as you drive through the car’s namesake neighborhood, or channel your inner Steve McQueen with a 1965 Ford Mustang GT289, both available for pick-up or delivery from One Stop Classics. Once you’ve secured a stellar vintage ride, start your day at The Beverly Hills Hotel’s Fountain Coffee Room, an iconic diner whose signature banana-leaf wallpaper saw Marilyn Monroe be romanced and Guns N’ Roses sign their first record deal. For lunch, head to Musso & Frank Grill, an American eatery that’s been serving Hollywood stars, from Chaplin to Bogart, since 1919. Be sure to also pay a visit to the Formosa Café, an old celeb watering hole built in 1939, where Ava Gardner would pile into the old, leather booths and John Wayne would nurse a late-night Scotch and where today Asian cuisine comes with a large side of nostalgia. When it’s time for a nightcap, look no further than the Frolic Room, a no-frills dive bar that started as a speakeasy and once called Frank Sinatra and Judy Garland regulars. And if you’re especially eager to pay tribute to the icons of Hollywood’s Golden Age, don’t miss the Hollywood Forever Cemetery, the final resting place of Tyrone Power, Mickey Rooney, Cecil B. DeMille, and many others.

Palm Springs

Known best as “Hollywood’s Playground,” Palm Springs has a long history of Golden-Age connections, dating all the way back to 1915. Less than a two-hour drive from LA, the desert town has been featured in dozens of films, but more importantly, it’s been the weekend retreat of choice for countless movie stars looking to escape for a few days. Hollywood’s biggest names would head to Palm Springs and hole up at its understated, elegant hotels and patronize its burgeoning food scene, and some even bought second homes in the remote community. 


Courtesy The Willows Historic Palm Springs Inn

Many of Palm Springs’s hotels have a residential feel to them, with just a handful of suites and villas and total private access, but The Willows Historic Palm Springs Inn was especially favored by Old Hollywood stars who visited the desert oasis. With only 17 guestrooms, the fabled hotel was founded as a private hideaway, a quality that attracted the likes of Shirley Temple, Billie Burke, Lynn Redgrave, and even Albert Einstein, and silent film actress Marion Davies actually lives at the Inn for some time. There’s also the Ingleside Inn, a romantic retreat with 30 garden rooms and suites that played host to a long list of iconic Hollywood stars. Elizabeth Taylor frequented Villa 8, the “royal suite,” with her seventh and last husband, Larry Fortensky, and Debbie Reynolds liked Villa 10, while Greta Garbo’s favorite room was 22, once called “The Hacienda,” and Marlon Brando stayed in 23, then “The Renaissance.” 

Related: What to Know When Planning a Luxury Palm Springs Vacation

Visitors don’t have to go far from these historic hotels to dine where the stars did, and those staying at Ingleside need walk just a few feet to the hotel’s famous restaurant, Melvyn’s. Once the property’s garage, the restaurant has had a few lives, starting as Orville’s, a spot for hotel guests only with a bar in the alleyway, and eventually becoming the incredibly popular Melvyn’s (named for the inn’s new owner Melvyn Haber) and the adjoining Casablanca Lounge. Here, stars, like Bob Hope, Marlon Brando, and Lucille Ball would dress to the nines in tuxedos and gowns and share laughs over a Steak Diane and escargot, a glass or champagne or martini in hand. Just a few streets over sits The Purple Room, a supper club tucked inside the Club Trinidad Hotel that’s rich with the sophistication and glamour of Hollywood’s yesteryear. Known as a favorite spot of the Rat Pack, the stage was frequented by Frank, Dean, Sammy, and many of their pals during the 1960s, and it was even where Sinatra proposed to his last wife, Barbara Marx. And for fans of Hitchcock’s ultimate leading man, check out Copley’s on Palm Canyon, an upscale American restaurant housed in Cary Grant’s former guesthouse. As the story goes, Grant purchased his Palm Springs estate in the mid-1940s and used it to host visiting friends and family, many of whom were considered Hollywood royalty, so the walls of Copley’s likely have more than a few star-studded stories.

San Diego


Courtesy Hotel del Coronado

Finish your road trip slightly further south in sunny San Diego. It may not seem like the most obvious home for Golden-Age-Hollywood history, but just two hours from LA, the coastal city has a wealth of cinematic ties. As a backdrop for some of the era’s biggest films, many of San Diego’s surroundings are recognizable to movie buffs far and wide, but its beautiful beaches and low-key attitude also led some Old Hollywood stars to vacation there. 


Courtesy La Valencia Hotel

Built in 1988 and designated a National Historic Landmark, the Hotel del Coronado is a well-deserving American treasure in its own right, but the wooden Victorian beach resort is especially known for its illustrious Hollywood history. As the backdrop for the wildly popular 1959 movie “Some Like It Hot,” The Del famously hosted Marilyn Monroe during filming, and it was reported that she liked poached eggs in the morning and snacked on the hotel’s vanilla soufflé later in the day. Charlie Chaplin stayed at The Del in 1920, while Lucille Ball and Desi Arnaz had a lengthy stay in 1950 while perfecting their “I Love Lucy” characters, and other celebrities, including Greta Garbo, Mae West, Rita Hayworth, Joan Crawford, John Wayne, Walt Disney, and many more visited the hotel during their heydays. La Jolla, another one of San Diego’s beautiful beach towns, was also a hotspot and “unspoiled jewel” for Old Hollywood stars, and many of them chose to stay at La Valencia Hotel. The nearly-100-year-old hideaway hosted some of the Silent Era’s most notable names, including John Gilbert and “First Lady of American Cinema” Lillian Diana Gish, but La Valencia’s most impressive Hollywood ties came during the 1950s. After the La Jolla Playhouse opened its doors in 1947, the hotel quickly became a gathering place for the theater’s founders and performers, including Gregory Peck, Dorothy McGuire, Ginger Rogers, Charlton Heston, and many more. Peck, one of the Playhouse’s founders and a La Jolla resident, made a habit of welcoming new guests at La Valencia’s Whaling Bar, and writer Raymond Chandler used the hotel as a thinly disguised backdrop for his thriller “Playback.” These days, the hotel still hosts quite a few celebrity guests, but the affectionately dubbed “Pink Lady” exudes the same exclusive allure even to its non-star-studded guests.