Day 1

Beaches and speakeasies on the Westside

I'm in Los Angeles, so of course I'm eating breakfast by the pool. More specifically, I'm in the lovely atrium at FIG, the poolside restaurant at the Fairmont Miramar Hotel in Santa Monica. In the water, a couple of kids are splashing around in unicorn floaties. On the wall above, Muscle Beach's best-known lifter, Arnold Schwarzenegger, flexes in a mural. On my plate is a scramble chock-full of fresh produce—tomatoes, asparagus, peppers, spinach—from Santa Monica's famed farmers market.

The pool may be Hockney-worthy, but these flip-flops were made for walking. Five minutes down Ocean Avenue, I cross a bridge over the Pacific Coast Highway and onto the Santa Monica Pier, passing the Route 66 sign, caricature artists, funnel cake stands, and carnival rides on my way to the end of the pier, where fishermen toss their lines in the water and tourists snap photos of a sea lion barking for scraps. The sharp salt smell of the ocean beckons, so I backtrack to the sand, where I roll up my jeans and watch the surf slide over my feet. I lose my thoughts in the rhythm of the waves, until a big one crashes in. Reverie over.

A prideful lifeguard tower on Venice Beach

Going wheels-up at the Venice Skatepark

I watch the surf slide over my feet, losing my thoughts in the rhythm of the waves, until a big one crashes in.

I keep flippin' and floppin' my way south toward Venice Beach, the epicenter of Southern California's grungy, punky beach culture. Snatches of the Doors leak from surf shops and sunglass stands on the very strip where Jim Morrison and Ray Manzarek formed the band. Are you a lucky little lady in the City of Light? Or just another lost angel… I kill a few minutes watching skaters ollie along the undulating walls of the Venice Skatepark, and then I exit the beach, going a few blocks inland to the Venice Canals. Developer Abbot Kinney built these narrow waterways in 1905 to evoke some other Venice, and while I don't see any gondoliers, the homes lining the canals make for a fun self-guided architecture tour, veering from glass-walled Modernist structures to mosaic-tiled hippie bungalows.

A few more blocks up Venice Boulevard, I reach the town's main drag, Abbot Kinney Boulevard. I'm having lunch at Gjelina, which for more than a decade has offered the sort of farm-fresh cuisine and casual-yet-sceney vibe that the rest of the world thinks is LA. I sit at a distressed-wood table and chow down on California king salmon tataki; grilled peaches with burrata, prosciutto, and chicory greens; and a perfectly cooked black bass with olives and heirloom tomatoes. If this is what people associate with LA, I can see why everyone wants to move here.

My feet are flip-flopped out, so it's a good thing my college buddy Matt, who lives in Hermosa Beach, has loaned me his car—a cobalt Chevy Volt we call the Blue Dragon—to help me navigate this unending city. Fortunately, you don't need to be a Targaryen to ride this dragon, so after retrieving the car from the Fairmont valet, I fly up the 405 to the J. Paul Getty Museum, which stands on a hill above the most heavily trafficked freeway in the U.S. I park and take the tram up, then meander through the Robert Irwin–designed Central Garden, following a trickling waterfall to a reflecting pool and an X-Files-esque azalea labyrinth. The scene is so transporting that it's easy to pass a couple of hours without even entering the galleries. Oops.

No time for regrets, though. The afternoon has begun to wane, so I drive back to the Fairmont and take a seat on my balcony to watch the curtain fall on another day in America. Once night has settled and the lights have come up on the pier, I walk over to the Third Street Promenade, an outdoor mallwhere fairy lights twinkle and purple jacarandas bloom above shoppers and buskers singing Justin Timberlake. At the food court, I go up an escalator and tap a code into a black door marked "private." When it opens, I enter Dialogue, an 18-seat tasting-menu hideaway that was one of just 24 restaurants in LA to receive a Michelin star this June. As he passes me the gorgeous plates (21 of them!), chef Dave Beran explains how the Roots' album …And Then You Shoot Your Cousin inspired his menu.

"I reached out to Questlove, and he told me they wrote that album over the course of the last year of their manager's life," Beran says. "It's essentially their progression emotionally. You had to experience that album the way they intended it, and that led us to the idea of writing a tasting menu that had to be experienced the way we intended. Just as the seasons look forward and backward, the dishes do as well. Every dish has something in it from the last one and something to look forward to in the next. Your snapper had a ginger mist on it, which went into the ginger-rhubarb foam, which leads to a rhubarb chip with matcha and lilac pudding, followed by a cucumber-lilac soda. None of our dishes are intended to be complete thoughts as much as completing each other's thoughts." Food for thought, indeed.

The landmark Venice Sign at sunset

After dinner, I'm buying Matt a drink as a thanks for lending me the Blue Dragon. I take a cab to Abbot Kinney and meet him at the restaurant Scopa Italian Roots, where we tell the maître d' we have a reservation at Old Lightning. He promptly confiscates our phones and leads us around to the side of the building, through an unmarked door, and into LA's premier bourbon bar. The glass case along the wall taunts us with shelf after shelf of nigh-impossible-to-find vintage bottles. Matt leers covetously at a collection of limited-edition Willett, while I pine for the Pappy. I tell the bartender, Jesús, that I love the wheated flavor profile of the Van Winkles but can't shell out $3,000 for a flight. He brings me a more affordable sampler: a delectably corn-sweet Old Taylor 6-year from 1980; an Old Fitzgerald made by a legendary Kentucky warehouse manager who stole from his stores to create his own sought-after blends; and a 101-proof Evan Williams 12-year that's normally available only in the Bluegrass State. "I hope you didn't drive," Matt deadpans, although I think he's just trying to confiscate my Old Fitzgerald. Not a chance, pal.

Day 2

Artful architecture and swinging nightlife in DTLA

Los Angeles may have an underrated metro system, but the city's true essence is found where the Blue Dragon and I now sit: in bumper-to-bumper traffic on the 10. I pull up my rush-hour playlist, and Guy Clark sings, If I can just get off of this LA freeway, without getting killed or caught…

Eventually, I reach the center of the city, which the Spanish founded in 1781 as El Pueblo de Nuestra Señora la Reina de los Ángeles but has in recent years been rebranded simply as DTLA. I'm starting the morning with a bite at Grand Central Market, a 1917 building that's home to all sorts of hip food stalls. I stop at the G&B Coffee counter and get an almond macadamia latte to sip while I wriggle to the Clark Street Bread stand, where I order avocado toast. It tastes like California.

On the other side of the market, I spot one of LA's signature architectural sights, the Bradbury Building. The interior of this National Historic Landmark, which was built in 1893 and features five floors of ornate iron railings and elevator shafts climbing toward an expansive skylight, looks both stunningly vintage and eerily futuristic. It's little wonder Ridley Scott chose it as the setting for the climactic scene of Blade Runner.

I exit through the side door and gawp at the Pope of Broadway, a soaring mural of Anthony Quinn on the former Victor Clothing Company building across the way, before continuing on through DTLA. This area was once so rundown that it wasn't much of a leap for Scott to imagine that by 2019 it would look like a post-apocalyptic dystopia, but over the last decade it has become the reenergized hub of the city, thanks to places like The Last Bookstore. This temple to the written word is probably best known for its second-floor book tunnel, which tourists and wannabe influencers line up to snap selfies in. I ask a clerk what he thinks is the definitive LA novel, and he points me to John Fante's Ask the Dust, which local literary god Charles Bukowski called "a wild and enormous miracle."

It's a good thing I picked up the reading material, because I'm going to have a wait at my next stop. One of the wonderful, contradictory things about this wonderful, contradictory city is that some of its best restaurants are in run-of-the-mill strip malls. One of these is Sushi Gen, in DTLA's Little Tokyo, where a long line has formed before the doors even open. I take my spot and read for a few minutes—Los Angeles, come to me the way I came to you, my feet over your streets … you sad flower in the sand—before I'm seated at the sushi bar, where a chef slings slices of Tsukiji Market–quality fish (buttery tuna, briney sea bream, sweet shrimp, creamy uni) at me until I wave my napkin in the air like a white flag.

The Pacific Seas bar at Clifton's

The afternoon sun is beating down and bouncing up off the pavement, so I elect to walk off my meal indoors, at The Broad Museum. The four-year-old building, which entrepreneur Eli Broad and his wife, Edythe, created to house their 2,000-piece collection, stands like a square of honeycomb next to the flamboyantly curvaceous Walt Disney Concert Hall next door—a contrast that associate curator Sarah Loyer tells me was very much intentional.

Jeff Koon's "Tulips" at the Broad Museum

"Where the Disney Concert Hall reflects light, our building draws light in," she explains. "The ceiling has 318 individual skylights that light the collection gallery. At peak sun hours we have all natural light." We ride the escalator up to the third-floor gallery, an acre of column-free space where pieces by Jeff Koons, Takashi Murakami, Yayoi Kusama, and Kara Walker are on display. I'm particularly struck by Deep Blue, an expansive mixed-media canvas by Los Angeles artist Mark Bradford. "It's inspired by the 1965 Watts Rebellion," Loyer notes. "You can see the map of the city grid, and the different dots and colors represent historic losses from that event."

We ride the Broad's escalator up to an acre of column-free space to see pieces by Jeff Koons and Yayoi Kusama

I thank Loyer for enlightening me and then zip over to the recently restored Hotel Figueroa, which features works from a new artist—often a Southern California woman—every quarter. I valet the Blue Dragon and take a few minutes to peruse Topanga-based painter Sophie Kipner's blind-contour portraits before stretching out on a poolside lounge chair with a Bohemia beer. When I mention to the waitress that something about the pool seems odd, she tells me it's shaped like a coffin. That seems like a bad omen for tonight…

But hey, if I gotta go, there are worse places to have my last meal than Nightshade, Top Chef winner Mei Lin's much-hyped new restaurant in the up-and-coming Arts District. A taxi drops me at a converted warehouse space that's an Instagrammer's dream—blond wood, white brick, mint and emerald green upholstery, and hanging plants—surpassed only by the presentation of the dishes: Hokkaido scallops in a coconut vinaigrette, chicharrón chunks with a bright green coconut and trout roe dipping sauce, prawn toast that tastes like Vietnamese spring rolls, Szechuan hot quail served atop Japanese milk bread (à la Nashville hot chicken). If the atmosphere is heavenly, that last plate is hellish; my eyes start burning upon its arrival, and it takes an extra glass of grüner to cool my mouth after its departure.

Let's keep turning up the heat! Clifton's is a DTLA institution, a Depression-era cafeteria that fed 10,000 people a day, eventually fell into disrepair, and was ultimately reborn as a four-story nightlife bazaar following a 2015 renovation. I climb past the giant trunk of an (admittedly fake) redwood tree to the top-floor Pacific Seas tiki bar, where I sit in a wicker chair under a mermaid statue and sip a Scorpion Bowl (rum, gin, cognac, orgeat, and god knows what else) that is, yes, set on fire by my waitress. Before I get stung, I descend one floor to the Brookdale Ballroom, where dancers in Gatsby-esque getups swing to a New Orleans jazz band. A woman sashays by me in a peacock-feather outfit, but she's gone before I can ask her if this is real or if I've been consumed by the flames of Szechuan pepper and Polynesian mixology.

Day 3

Hollywood history and Eastside eats

It was all real, and I'm paying for it now. Good thing I know the perfect place for a clean-living kind of breakfast. Sqirl is on the edge of East Hollywood, in an area that's still dotted with 99-cent stores, but the line of part-time models waiting outside betrays its hip quotient. I make my way to the counter, order an Horchoffee (vegan horchata shaken with a double espresso) and a Crispy Disco (brown rice with mint, cilantro, cucumber, scallion, avocado, fried egg, and sausage), and grab a seat at the sideboard. The restaurant's sprightly owner, Jessica Koslow, brings over my food and gives me a playful punch on the knee as she takes the stool next to mine.

"It was a lot of pressure to be this funky place and be like, 'Here's what's happening in Los Angeles,'" the Long Beach native says, recalling the rapturous reviews she received after opening in 2012. However, she does take pride in being an evangelist for SoCal cooking. "There are so many different pockets of LA that [its cuisine] is hard to describe, but if you want a neighborhood restaurant for LA, you're here."

The Angel of Breakfast gives me a hug and waves me back to my food. After devouring the Crispy Disco, I head to The Hollywood Roosevelt hotel. Upon checking in, I rendezvous with Tours by Locals guide Jasmine Jia, who takes me on a winding drive through Griffith Park to the Griffith Observatory. The triple-domed Greek Revival building is one of LA's most recognizable—it can be seen in Rebel Without a Cause and La La Land—but Jia tells me it almost didn't get built. The city turned down funding from tycoon Griffith J. Griffith in 1912 because he had infamously shot his wife (who survived) a decade earlier. "There was a sensational trial," Jia says. Griffith re-donated the money when he died in 1919, and the Observatory was completed by the WPA in 1935. Today it's both an interactive astronomy museum and a spot from which you can see the Pacific Ocean, DTLA, Dodger Stadium, and the Hollywood sign.

The soup bowl–size chalices of salty, limey beer are garnished with shrimp, and the straws are even crusted with tamarind candy.

Now, the question every tourist in LA inevitably faces: Should I take a picture with the sign? As we drive over, Jia tells me it was erected as a real estate advertisement in 1923, when it originally read "Hollywoodland." "The land was sold, and the sign should have been taken down," she says, "but it became associated with the movie industry and LA and became a landmark." It was later shortened to Hollywood—better to fit the photo Jia snaps of me from the vista point in Lake Hollywood Park below.

Jia drops me back at the Blue Dragon, and I head to a far less touristed part of the city. Another college buddy of mine, Rob, was born and raised in Cypress Park, his parents among the tens of thousands of Mexican immigrants who settled on the east side of the Los Angeles River, and I've asked him to show me a couple of off-the-radar spots. I cross the concrete riverbed into Boyle Heights and meet him at El Tepeyac Café, an institution that serves old-school Mexican food. Rob points me toward the gargantuan chile verde–slathered Original Hollenbeck burrito, which is stuffed with rice and beans and guacamole and pork and comfort. Next, we zip over to La Chupería, in neighboring Lincoln Heights, where the bartender brings us two micheladas, soup bowl–size chalices of salty, limey beer (a Modelo bottle floats mouth-down in each cup) rimmed with chili sauce and garnished with cucumber, celery, and shrimp. The straws are even crusted with tamarind candy. As we slurp our drinks and watch a replay of the previous night's Dodgers game on the TV, I ask Rob what places like this mean to LA, and if he's worried about them disappearing as the city changes.

The busy lanes at Highland Park Bowl

"Gentrification brings restaurants and nightlife to areas that were overlooked, but now you have these immigrant-run mom-and-pop businesses, which have contributed so much to LA's cultural identity, operating under the threat of extinction," he tells me. "Without culture, LA risks losing its home too."

I thank the homie for the knowledge, and we split up with plans to meet later. I really need to stretch my legs, so I head to Echo Park. A popular walking path circles the lake where Jack Nicholson's J.J. Gittes snapped compromising photos of Hollis Mulwray in Chinatown, but today it's strangely calm: just a couple of teenagers lazily peddling swan boats and a few kids quacking at the ducks near the shore.

Feeling a little lighter, I get back in the car and cruise up Sunset Boulevard, shopping my way through LA's hippest 'hood, Silver Lake. I browse kid-centric bios of Prince and Bowie at MRKT, whip-stitched watchbands at Dean, and vintage rock 'n' roll tees at Sick City Records. Past the junction with Hollywood Boulevard, I make a pilgrimage to the swirling mural that appeared on the cover of Elliott Smith's Figure 8 album. The storefront has changed tenants several times—it's now a well-regarded Filipino restaurant—but most of the artwork remains, serving as a shrine where fans of the deceased songwriter still leave remembrances.

Echo Park Lake

We order frozen White Russians and 'Dead Flowers' comes on. I'm pretty sure we're in a Big Lebowski dream sequence.

Nostalgia makes me hungry. Dinner is at Majordomo, superstar chef David Chang's first California restaurant. I'm joined by Rob and Matt (who has come to reclaim the Blue Dragon) at a table beneath a skylit warehouse ceiling, and we go in on silky tofu topped with uni and avocado, dungeness crab mafaldine pasta, and a pot of boneless chuck short rib onto which our waiter slices a hunk of raclette. "Has anyone ever asked you to carve it straight into their mouth?" Matt asks. "All the time," the waiter replies.

We continue the impromptu reunion at another one of Rob's favorite spots, Highland Park Bowl. A diverse young crowd rolls strikes inside the 92-year-old bowling alley, LA's oldest, which is decorated with league championship banners from decades gone by. We order a round of frozen White Russians, a cocktail the bar calls The Dude Abides, and as we lace up our shoes, the Rolling Stones' "Dead Flowers" comes on. I'm pretty sure we're in a Big Lebowski dream sequence, but I don't see any purple jumpsuits, and the only thing that's nihilistic is the score of our game.

I hug my friends goodbye and hail a ride back to the Roosevelt, where I slip into a robe and look out the window of my suite. Hollywood Boulevard is asleep; the only stars sparkling are the ones embedded in the sidewalk. Good night, stars. Good night, moon. Good night, Los Angeles. I'll see you soon.