San Francisco and Big Sur Roadtrip: A 10 Year Look Back

Reflecting on one of my earliest adventures brings a wave of nostalgia, transforming it into an unforgettable chapter of my life, perhaps my most memorable “first.” This was a period marked by an open embrace of the unknown, despite the budget constraints that shadowed my youthful days.

At that time, in 2013, I was navigating through a bustling schedule, I was juggling 20 hours a week at massage school during the evenings and managing a kitchen for 40 hours a week at a restaurant close to the University of Austin’s campus. I even waited tables for breakfast shifts over the weekend, starting at 4 a.m. On top of that, being 21, my weekends were filled with parties, must I say it shamefully, Dirty 6th Street, all while navigating through the aftermath of a breakup from a year-and-a-half-long relationship. It was a memorable year, to say the least, marked by a period where sleep seemed like a luxury I couldn’t afford.

The trip to San Francisco with my best friend from middle school, Paulina, remains an unforgettable highlight. Recently (2023) revisiting the city after a decade only added layers to my appreciation of how some things change while others remain steadfast. You can view that blogpost here:

2 Week RoadTrip Through Northern California

This blog entry holds a special place in my heart, as it marks the beginning of a journey that’s profoundly personal to me. I vividly remember visiting California for the first time and dreaming of sharing it with the person I hoped to spend my life with. And a decade later, I had returned with my fiancé, Adam! It’s incredible to think it’s been ten years since my last visit to San Francisco. Let’s not wait any longer—join me as I take you on a heartfelt 10-year journey back through cherished youthful memories!

Day 1: San Francisco

Our journey kicked off with Paulina driving up from San Antonio to Austin, from where we flew to San Francisco. This trip marked my first adult girls’ trip, brimming with excitement and anticipation.

Upon arrival, we were warmly received by Nikola, a friend I used to bartend to in my San Antonio days, who introduced us to the city’s charm and its daunting hills, challenging my bathmophobia (a fear of downhill slopes) head-on. We stayed with Evan, a kind individual I met through couchsurfing.com, who offered his couch off of Ocean Ave for free. Looking back, staying with a stranger, especially being so financially constrained, was a gamble, but it turned out to be a memorable part of our trip.

I still remember a gamer in the corner of the living room, perpetually immersed in League of Legends, tirelessly playing when we’d return and still battling on when we awoke. Now, in retrospect, this relentless dedication adds a humorous touch to our stay, leaving me wondering when, if ever, he found time to sleep.

Despite the cold weather—a stark contrast to Texas’s summer heat—we ventured towards Fisherman’s Wharf in search of warmer clothes, already dipping into my budget. The Farmer’s Market at the Ferry Building was an eye-opener with its surprisingly affordable produce, a memory that stands out amidst the fog of inflation and changing prices over the years.

Our stroll took us towards Coit Tower, admiring the Victorian architecture along the way—a testament to my love for historic buildings. The view from the tower and the blooming flowers around the city filled me with joy. Our day concluded with a stroll through Chinatown, a vibrant and unique experience unlike anything back home in Texas.

Day 2: Exploring SF Further

Our exploration continued with a trip to Golden Gate Park, starting at Hippie Hill, where we encountered a hippie on a skateboard, openly selling weed—this was before it became legal in the state. In a moment of boldness, possibly fueled by the spirited atmosphere, I jokingly inquired if he had any magic mushrooms. To my surprise, he took me seriously, signaling to another individual who swiftly approached us, eager to fulfill the request. Before I fully grasped the situation, I found myself exchanging cash for mushrooms, a transaction that unfolded with surprising speed and left me with a mix of excitement and apprehension.

As we meandered through Golden Gate Park, I was struck by its sheer beauty and expansiveness—apparently, it’s 200 acres larger than Central Park in New York, a city I had visited just a few months prior. There’s something special about cities that boast such large, green sanctuaries amidst urban sprawl. The Japanese Tea Gardens within the park were a particular highlight for me. As someone of Japanese heritage, the authentic mochi and matcha, along with the serene setting, evoked a sense of home and familiarity that was deeply comforting.

Our exploration led us to Twin Peaks, where, despite being ill-equipped with cheap sandals and no water, we embarked on the hike. The effort was rewarded with breathtaking views, affirming our decision to make the climb. Hungry from our exertions, we made our way towards the Castro district, happening upon the Concrete Slides of Castro by chance. The slides offered an unexpected and delightful diversion, capturing the whimsical spirit of the city.

The day’s wander eventually took us to Haight-Ashbury, a neighborhood that resonated deeply with my 21-year-old self. The area’s distinct hippie and LSD-influenced vibe, along with its unique steampunk shops (many of which are sadly no longer there), was utterly captivating. It was here that a bartender suggested we rent a car and drive to Big Sur. Despite my financial constraints, the allure of driving Highway 1 and experiencing its renowned beauty was too tempting to resist. Thus, in a decision that epitomized the spirit of exploration, we opted to charge the rental to a credit card, setting the stage for the next leg of our unforgettable journey.

Day 3: Napa Valley to Pigeon Point

We took an upscale turn when we decided to rent a convertible, fully embracing the spirit of spontaneity. Despite my financial concerns, looking back a decade later, I harbor no regrets about that decision. The convertible, complete with full insurance and the added costs for being under 25, was a splurge. My bathmophobia meant that Paulina took the wheel, allowing me to enjoy the drive without the stress of navigating downhill slopes myself.

Complicating our road trip was the fact that our convertible lacked an audio cord for phone connectivity, and with the radio out of commission, we were left with only a CD that a co-worker burned for me. This single CD became the soundtrack of our trip, playing on repeat and embedding itself as the musical backdrop to an array of unforgettable memories, now encapsulated in a Spotify playlist for nostalgia’s sake.

With our newfound freedom, we set our sights on Napa Valley, a destination that promised the allure of vineyards and fine wine. Our intuition led us to the St. Helena Visitor’s Center, where we were fortunate to receive a free wine tasting voucher for V. Sautti Winery. This vineyard remains unmatched in my memory; the wines there, particularly the Gamay Rouge, introduced us to a level of quality and taste that was both unexpected and unparalleled. The Gamay Rouge, a remarkable rosé still in production today, left a lasting impression on us and everyone we’ve since shared it with. The ambiance of Napa Valley, enhanced by the perfect weather and the luxury of our convertible, made for an unforgettable day.

As the day transitioned into evening, we ventured south with the aim of exploring Big Sur, but not before an unplanned dinner at the Ritz-Carlton at Half Moon Bay. Unfamiliar with the prestige of such an establishment at the time, our casual attire did little to dampen our spirits. We reveled in the atmosphere, embracing the moment despite our underdressed appearance.

The day concluded at a hostel in Pigeon Point, an enchanting place with its own lighthouse. The hostel offered more than just a place to rest; it had a jacuzzi perched on the cliff’s edge, where we could relax to the soothing sounds of crashing waves below—a memory of cheerful bliss.

Day 4: Santa Cruz and Big Sur

I was dawned with a sense of eager anticipation for the road ahead. However, our plans took an unexpected turn when Paulina awoke with bloodshot eyes. Now, here’s something about Paulina that you should know—she possesses a unique ability to see and communicate with ghosts, and even predict death. She even knew I died Near Death Experience in 2012. But that’s a tale for another time. On this particular morning, she recounted encountering a persistent little girl throughout the night, who repeatedly yelled, “I want to go home,” much to Paulina’s sleep-deprived dismay. While my initial reaction was to burst into laughter, Paulina’s exhaustion demanded a more immediate remedy, so we promptly secured her a much-needed cup of coffee from the hostel.

Our path continued southward, leading us to the captivating landscapes of Año Nuevo State Park, where we were treated to the sight of majestic elephant seals, their presence adding a touch of wild beauty to our curiosity. The tranquil walk amidst nature’s wonders provided a welcome respite from our urban escapades.

Our next destination was Santa Cruz, where we found ourselves spending the afternoon enthralled by the lively atmosphere of the boardwalk. We encountered every roller coaster ride, embracing the exhilarating thrills of each twist and turn. Energized by our time in Santa Cruz, we resumed towards Big Sur, a destination we approached with a sense of wonder.

As we arrived in Big Sur, we were greeted by breathtaking vistas that stretched as far as the eye could see. With little in the way of planning, we allowed ourselves to be guided by the allure of the scenery, reveling in the freedom afforded by our convertible. An inexplicable desire to voyage the rugged beauty of Big Sur led us to embark on a quest to find the perfect spot for a bonfire and a night under the stars.

Yet, our quest proved more challenging than anticipated, as we discovered that bonfires and overnight stays were prohibited on the beaches of Big Sur. Undeterred, we made the most of the situation, savoring a bottle of wine from V. Sattui as we watched the sun dip below the horizon. Exhausted from our day and with nightfall descending, we found ourselves next to a cabbage farm, unsure of our exact location, ultimately deciding to seek refuge in the comfort of our convertible, a makeshift shelter under the vast expanse of the night sky. It was a humbling conclusion to a day filled with the unexpected, reminding us of the unpredictable beauty of life on the road.

Day 5: Redwoods back to SF

This day brought with it a sense of mystical introspection. Upon waking, we eagerly set out for the nearest beach, where we were greeted by the flicker of a small fire illuminating the shoreline made by street people. It was a moment of sheer delight, as we finally found ourselves immersed in the idyllic scene we had been yearning for. However, our time on the beach was fleeting, as the looming deadline to return to San Francisco and relinquish our trusty convertible compelled us to bid farewell to the shore all too soon.

Determined to make the most of our journey back, we resolved to take a different route, opting to traverse through the enchanting landscape of Big Basin State Park. It was here that I made the impromptu decision to indulge in the magic mushrooms procured from the hippie at Hippie Hill—a choice that would ultimately lead to an unforgettable altered perception with nature’s wonders.

As the effects of the mushrooms took hold, I found myself enveloped in a kaleidoscope of emotions, deeply attuned to the ancient wisdom of the towering redwoods surrounding us. The sheer magnificence of the forest, coupled with the potent influence of the mushrooms, transported me to a realm of profound introspection and connection with the natural world, I began to cry.

However, the intensity of the psilocybin journey proved overwhelming for Paulina, who, as the designated driver, began to feel the effects of the mushrooms vicariously through me. In a surreal twist of fate, she found herself temporarily incapacitated, forgetting how to operate the vehicle amidst the pulsating energy of the redwood grove.

Undeterred by this unexpected turn, we embraced the opportunity to linger in the tranquil embrace of the redwoods, allowing the effects of the mushrooms to gradually subside until it was safe for us to continue our drive. Reluctantly bidding farewell to the serene sanctuary of Big Basin, we returned the convertible, our hearts still humming with the echoes of our woodland reverie.

With time to spare before our departure, we seized the opportunity to visit the iconic Painted Ladies, their vibrant hues standing in stark contrast to the verdant tranquility of Big Basin. It was a fitting end to our quest, a poignant reminder of the kaleidoscopic tapestry of enjoyments that had woven together to create a truly unforgettable expedition.

Day 6: Reflections and Departures

The last day always marks the bittersweet conclusion to our whirlwind bonding, and we were determined to make the most of our remaining time in San Francisco. Eager to immerse ourselves in the vibrant energy of Japantown, we set out to explore its myriad delights. As someone of Japanese descent, I felt a deep connection to this cultural enclave and was eager to devour in its culinary offerings and cultural attractions. From traditional eateries serving up authentic Japanese cuisine to quirky shops brimming with treasures, every corner of Japantown beckoned with promise.

We pampered in a delightful hot and cold soak at the Japanese communal bathhouse of Kabuki Springs & Spa, treating our bodies to a rejuvenating paradise. While I had visited many bathhouses in Japan before, it was Paulina’s first time experiencing anything of the sort, and she found it to be her favorite excursion of the entire trip. The atmosphere was incredibly relaxing. It was during our time at Kabuki Springs that my fascination with bathhouses and natural hot springs in the United States truly blossomed. I am definitely planning to write an article about this specific topic in the near future!

One other particularly memorable find was a bustling arcade filled with fun and games, offering a nostalgic escape into a world of whimsy and wonder. Here, we engaged in rounds of classic arcade games and even stumbled upon a whimsical Japanese photo booth, where we couldn’t resist capturing a few cliché but endearing snapshots to commemorate our time together.

As the day unfolded, we found ourselves utterly captivated by the myriad activities Japantown had to offer, losing track of time as we savored every moment of our final day in the city. Our CouchSurfer host, Evan, regaled about a revolutionary new concept called Lyft—an app-based ride-sharing service that promised to revolutionize transportation in the city. Intrigued by the idea, we decided to seize the opportunity and experienced our first Lyft drive, embracing the convenience and novelty of this innovative mode of transport. Rather than the app deciding on an algorithmic price, we just negotiated with the driver.

Returning to our temporary abode, we found ourselves greeted by the familiar sight of our gaming host engrossed in his digital world, a testament to the diverse array of characters we had encountered throughout our travel. With a few precious hours remaining before our flight back to Austin, Paulina and I made an impulsive decision to drink the last remnants of our V. Sautti wine collection, fully aware of the potential consequences of inebriation before a flight.

Perched atop a rooftop overlooking the sprawling expanse of San Francisco, we raised our glasses in a toast to the unforgettable and lasting memories we had shared over the past week. Despite the slight extravagance and the inevitable strain on our budgets, there was no denying that this trip had been nothing short of extraordinary—a testament to the transformative power of travel and the enduring bonds forged through shared experiences. As the sun dipped below the horizon, casting a golden glow over the cityscape below, we reflected on the journey that had brought us here and the countless adventures that awaited us on the road ahead. Truly, it had been an incredible outcome —one that would remain etched in our hearts and minds for years to come.