Savoring old Hollywood through Los Angeles’ most iconic restaurants and landmarks

For those of us who love the history, culture, celebrity — and yes, the salaciousness — of Los Angeles, but don’t go as often as we’d like due to the sometimes unbearable drive there and back, fret not: here is a perfect plan for a super-fun, stress-free getaway.

Nowadays, when I head to the City of Angels, I skip the traffic and take the Amtrak Pacific Surfliner. The easy-breezy, three-hour coastal trip to downtown Los Angeles is often faster than driving, the view is gorgeous, and you can sip wine or coffee along the way. Arriving at beautiful Union Station, an architectural gem, sets the tone for the weekend. From there, it’s a 10-minute Uber, cab, or car service ride to my L.A. home away from home, The Aster. Located at the corner of Hollywood and Vine in the heart of Hollywood, this property is a “hybrid” membership club and guest hotel. Originally built as the Hollywood Post Office in 1925, this 35-suite, adults-only hangout attracts the movers, shakers, and up-and-comers of show business. While in the members-only club, which you have privileges to when you stay as a hotel guest, you can eavesdrop on creatives “taking meetings,” as they say in the business, and making deals. It’s an invigorating atmosphere to make your Hollywood home base.

On my most recent stay, the streets surrounding The Aster were closed off in the wee hours while they were filming chase scenes for the film The Adventures of Cliff Booth, Quentin Tarantino’s sequel to Once Upon a Time in Hollywood, starring Brad Pitt. Yes, Brad Pitt was “in the house.” Well, technically outside — but I still managed to get a bird’s-eye view from the rooftop bar.

Just one star-studded, “Walk of Fame” block from The Aster and next-door to the Pantages Theatre sits the Frolic Room, one of Hollywood’s most storied dive bars. Originally a Prohibition-era speakeasy, it was later owned by Howard Hughes and has welcomed everyone from glitzy Oscar winners to gritty regulars like Charles Bukowski, who reportedly wrote chapters of his novels from a corner stool reserved in his name. Legend has it the Frolic Room was also the last place Elizabeth Short, a.k.a. The Black Dahlia, was seen alive before her infamous and still unsolved murder.

On a brighter note, another not-to-miss piece of L.A. history is The Apple Pan. This tiny, U-shaped, counter-only diner, housed in a historic white bungalow on West Pico Boulevard, has been open since 1947. The neon sign out front pledges their motto, “Quality Forever,” and they mean it. The Apple Pan offers classic American fare — burgers, fries, and pie — all served in paper boats. This iconic eatery has been featured in many movies and TV shows over the years, and some of us of a certain age will recognize it as the popular fictional hangout, The Peach Pit, from Beverly Hills, 90210.

You’ll probably wait in line, but this place is worth it. They’ve been doing smash burgers before “smash burger” was even a term, and you just may spot a music mogul, movie star, or model donning a ball cap and dark glasses while feasting on a Hickory Burger and banana cream pie.

Well worth the ride into Santa Monica, Chez Jay is another legendary spot to lay low and go casual. This iconic bar and restaurant was opened by part-time actor and full-time swashbuckler Jay Fiondelli, and named after the supper club Chez Joey from his favorite Sinatra film, Pal Joey. It has appeared on film over the years and most recently served as Billy Bob Thornton’s character’s watering hole in the series Goliath. Simple fare of steaks and seafood meets checkered tablecloths and a cluttered, nautical-themed room. In one of its more famous tales, astronaut Alan Shepard, a Chez Jay regular, reportedly smuggled one of their free bar peanuts aboard Apollo 14 at Fiondelli’s urging. When Shepard returned the peanut after the mission, Fiondelli carried the “astro-nut,” as he coined it, in his pocket, showing it off to guests and holding court until his death in 2008. The peanut sits in the family safe, as the story goes.

Two more vintage Hollywood eateries worth the hard-to-get reservations are Musso & Frank Grill, which opened in 1919, and Dan Tana’s Restaurant, open since 1964. Both flank original décor, celebrity sightings, and the standard fancy fare: steaks, chops, pasta, and goblet-sized martinis presented in ice baths at your table.

And if you really want to get your celebrity on, book a bungalow at Chateau Marmont.  Built in 1929, the property’s 43 suites and bungalows, each with living rooms and kitchens, boast residencies from Roman Polanski and Sharon Tate to Helmut Newton and John Belushi. The Chateau remains a sanctuary for artists and celebrities working (and playing) in Los Angeles. Rooms are as pricey as you’d expect, and photos are forbidden in common areas to protect guests’ privacy — but there’s nothing stopping some good gawking.

In a time when everything seems to be designed for instant gratification and “gram-worthy” shots, there is something romantic and intriguing about visiting places with rich histories that have endured the years unapologetically unchanged. Los Angeles is filled with hotels, restaurants, old theaters, and bars — all with walls that could tell a thousand stories — and if you sit at the bar long enough, one of the regulars probably will.  

It’s the stuff that movies are made of.