San Francisco Once Broke My Heart. This Trip Made Me Fall in Love Again.

From Oprah Magazine

Made in the USA is an OprahMag.com series that explores American cities. While social media makes it seem like real travel means escaping to far-flung locales, this series is an ode to the best places to road trip—or staycate!—right in our own backyard.

“One’s destination is never a place, but a new way of looking at things.” Henry Miller wrote those words in the story of his years in California, and the sentiment was on my mind as I made my return to San Francisco to seek fresh adventure—for exactly 72 hours.

Until this past August, I hadn’t been back to San Francisco since I lived there nearly twelve years ago, nor had I revisited my own deeply complicated personal history with the place. My first encounter with the Bay Area came right after college graduation, when my then-boyfriend convinced me to join him, his dog Irie, and his musty collection of imitation Pendleton blankets in a big cross-country move. I had never even been to California before, but I was in love and absolutely nothing held me back in New York. So we packed up his parents’ old Volvo and headed west.

In the weeks following our arrival, several things became crystal clear: My hippie boyfriend and I were wildly incompatible, San Francisco weather was MUCH different than what my Baywatch-fueled/geographically-ignorant impressions of California had led me to expect, and that entire part of the country was intent on chewing me up and spitting me out. (Speaking of chewing: Irie had eaten all of my bras.)

I experienced my first major heartbreak in San Francisco, when Mr. Dreamcatcher gave me the boot after three months. And while I’d spend over a year more in S.F. living with the few friends I had there, I mostly recall walking around broke and alone, with Morrissey lyrics blaring from my headphones as I scrunched my face against the Outer Sunset’s near-constant cold front.

I was 22 then, lonely, homesick and only beginning to figure out how to move about in the world. Sure, I had a gorgeous view of the ocean every morning as I walked to the Muni streetcar that took me on an equally picturesque ride to work. And I had my fair share of fun when I wasn’t sobbing over my ex, too, but I never felt fully…there. I hadn’t yet realized what I know now: That anyone’s perception of somewhere new—especially a city—isn’t objective reality. It’s shaped by who you are, the people you’re spending time with, and the experiences you have.

That’s why, when Chase Sapphire invited me to spend a long weekend in San Francisco for the Outside Lands music festival, I jumped at the chance. I was more than ready to overwrite my (literally) foggy memories—and to get to know the city again, this time with my O colleague Molly Simms. Our friendship goes all the way back to our college days at Sarah Lawrence, and she even visited me in San Fran way back when; who better to return to the scene with?

Our first stop upon arrival was the Stanford Court, a boutique hotel in Nob Hill. The elevator rides were soundtracked by Bay Area greats (Counting Crows, E-40, Tony! Toni! Toné!), and our corner room welcomed us with highly 'grammable views. As I admired the iconic Transamerica Pyramid, cable cars ding-dinged down below at street level; we’d been in the city for barely an hour and we were already one Tony Bennett song away from being the San Francisco-est.

We hopped in a cab and headed to the Mission District, my old stomping grounds, where I was delighted to find that the authentic Mexican food options are still plentiful. The enchiladas poblanas at Puerto Alegre were delicious, and I probably did not need that second margarita, but what’s a girls’ trip without a daytime buzz or two?

After a couple hours of mural-peeping and shopping along Valencia Street, it was time for an early dinner (that three-hour jet lag was hittin’ hard). Che Fico, a hotspot that already had eager diners lining up on the staircase at 5:30 p.m., served up plate after plate of their “Cal-Italian” fare. Though their pizzas garner the most buzz, the chopped antipasto salad and pasta dishes are the things I wish were in front of me again right now.

The next morning, after amping up with some Blue Bottle coffee (fun fact: they’re headquartered across the bay in Oakland) we headed to Outside Lands, a festival held in Golden Gate Park. While music is front and center, boasting a lineup featuring Paul Simon, Childish Gambino and my country-pop queen, Kacey Musgraves, the annual event is sprawling. There was brand-new territory to discover around every corner: Wine Lands, Beer Lands, and the uber-Californian Grasslands, which “spotlights the celebration, education, and integration of cannabis products into daily life.” It was essentially an open-air market where over-21 festivalgoers could purchase joints, gummies, THC vape cartridges, and everything else they’re putting weed in these days. And, yes, there was a smoking section.

Saturday was a full day of watching music in delightfully comfy sweater-weather, including a stageside viewing of Big Wild’s set, courtesy of Chase Sapphire. But Sunday was, dare I say, the best San Francisco day of my entire life. Back when I was a sullen, recently-dumped resident working a part-time temp job, I somehow never made it to one of the city’s most popular attractions: Fisherman’s Wharf. Touristy as it may be, the draw was all about the three S’s: Seafood, stunning vistas, and SEA LIONS.

After putting away a dozen oysters while admiring Alcatraz and the Golden Gate Bridge, we said hello to those magnificent, be-whiskered beasts on the pier, then made a pit stop for some Salt & Straw ice cream. Then, it was time to catch Kacey Musgraves at Outside Lands; watching her open her set with “Slow Burn” as the afternoon sun shined above and a glass of white wine in my hand was pure perfection.

We capped off our last night in San Francisco with a full-circle moment: Drinks at the Tonga Room & Hurricane Bar. The restaurant and bar nestled in the Fairmont Hotel is infamous for a man-made lagoon upon which a band plays Top 40 covers in a boat and get periodically “rained” on. It was actually my second time visiting: The first was back in my early twenties and, incredibly, Molly was with me that time, too. At 23, I’d never heard of a Tiki bar before, so I was suitably bowled over by their over-the-top glam décor, and I'd also had no idea that drinks could cost more than five dollars. It felt pretty great to come back, so many years and Mai Tais later, to discover that while I was still awed by the atmosphere, I was one thousand percent more at ease.

My long weekend in S.F. canceled out every bad memory I had of my past time there—though fortunately, I’ll never forget the lessons. I now associate the city with perfect temperatures, delicious food, and laughing till I cry while huffing and puffing up the crazy-steep California Street, promising Molly we’d both have “tight, San-Francisco-style tushes” by the trip's end. It turns out fog is pretty cool when it’s not a meteorological allegory for your situational depression. Was the bay always this sparkly?

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