On a rainy day in 2002, my then-girlfriend and I left Gold Beach and continued our Pacific Coast Highway road trip by driving up the Oregon coast slowly, stopping to enjoy the ocean views and experience local flavor in each tiny coastal town. When we drove through Oregon's long stretch of sand dunes, we stopped to photograph ourselves in front of the dunes. From dark Pacific Northwest clouds, rain poured down, soaking our hair, but it only invigorated us as we moved closer to Seattle, excited to live together for the first time.

San Francisco's art deco Golden Gate Bridge appears through fog under overcast skies in 2006.

Meanwhile, on an equally gray morning in 2006, after having sped through Redwood National Park at dusk the evening before, my brother Brian, his girlfriend Beatrice, my friend Brad, and I continued toward my new life in Los Angeles. Under a gloomy sky, we drove over a Golden Gate Bridge enveloped in mist and took obligatory portraits in front of the art deco masterpiece. Aiming to complete a whirlwind one-day tour of San Francisco, we played the part of frenzied tourists well. We navigated our car down Lombard Street (the most crooked street in the world), we ate crab at famous Castangola's (one of the oldest restaurants on Fisherman's Wharf), we took a trolley ride through the city, we ate delicious Dim Sum at Cold Mountain in Chinatown, and we strolled through Union Square.

San Francisco's Lombard Street is the most crooked in the world.

Frazzled from the big-city pace, we took a relaxed detour through the dramatic 17 Mile Drive at Pebble Beach. We watched sea lions, gazed at Cypress trees, and marveled at the peculiar description on an informational sign of rugged Joe Point, a rock formation off the coast: "Joe was a Chinese man who lived alone in a driftwood home near this point in the early 1900s... No one knows for sure if the Point was named after Joe or if he was named after the Point."

Mulling over Joe's mystery, we continued on to the winding highway through desolate Big Sur, the same stretch of road that started the journey to Seattle with my girlfriend four years before, this time at night, under a full moon. I couldn't help but think of the optimism my girlfriend and I had shared as the four of us drove in the opposite direction. On the tops of Big Sur mountain crags, we stopped frequently to stare into the dark, watery void below us, with only a stripe of reflected moonlight visible in the Pacific Ocean.

Meanwhile, on my recent 2009 PCH road trip to help my friend Erin move her life to Los Angeles, she and I enjoyed a surprisingly first-rate breakfast of blueberry pancakes and an omelet at patriotic Mattie's Pancake House in Brookings, Oregon. We then proceeded leisurely to the Avenue of the Giants, a 31-mile scenic road through Humboldt Redwoods State Park, which brings cars within inches of enormous Redwood trees along the highway. When my brother, friends, and I drove near here in 2006, we arrived at the Redwoods too late at night to experience the wacky tradition of driving a car through a hollowed-out tree. This time, however, Erin and I were right on schedule, albeit in the pouring rain. Excitedly, we paid a four dollar fee and inched our car forward, penetrating the narrow opening at the tree's base. Heavy rain soaked us while we took photos of our dubious accomplishment, and we quickly pulled our car out of the hole. Admittedly, it was a mildly sexual experience -- but probably not worth four dollars.

Big Sur is home to California's most beautiful coastline.

We spent the night in Palo Alto, where the Palo Alto Creamery served us the best blueberry pie of our trip, and we continued our California culinary tour the next morning with fried artichokes at the World Famous Giant Artichoke Family Restaurant in Castroville, California. Filled with artichokes, we began navigating the hairpin curves of Big Sur yet again, this time in the daylight. At viewpoints, I pretended to push Erin over the edge of the perilous cliffs one time more than she thought funny, but the embarrassing secret photos she took of me peeing off a steep cliff into the ocean made up for my antics. After a short hike to the Pfeiffer Falls waterfall just off the highway, we navigated the car over the ragged cliffs and followed the snaking road toward San Simeon.

San Simeon Pier reaches into the Pacific Ocean from William R. Hearst Memorial State Beach in California.

Erin and I bought tickets for the Hearst Castle Experience Tour (recommended for first time visitors) in San Simeon, and we took a bus to the top of a mountain above William Randolph Hearst's ranch, upon which his mansion sits. Our incompetent tour guide was a woman remarkably adept at sharing with us, in an unidentified (fake?) accent, only the most tedious possible anecdotes about the estate's history. As she slipped in and out of her baffling character, it became clear to us that she couldn't decide whether we were imaginary guests visiting Hearst during his era or simply tourists in 2009 hoping for insipid factoids. But even she couldn't ruin the lush views of San Simeon, the spectacular swimming pools, and the remarkable lavish Castle architecture. Some well-timed iPhone Wikipedia research allowed us to give ourselves a tour within our tour. Our tour was more fascinating, consistent in tone, and lacking a Welsh-Bombay-French Canadian accent.

A sculpture of an artichoke sits outside the World Famous Giant Artichoke Family Restaurant in Castroville, California.

When Erin and I left Hearst Castle, we left PCH and drove on the 101 into Hollywood. As we passed through Hollywood tourist-ground zero in her purple Toyota -- the intersection at Hollywood Blvd. and Highland Ave. -- the reality of Erin's move from Seattle began to feel real. She felt nervous about switching careers, especially in a challenging economy, but she pushed forward anyway. Having accomplished the same thing just three years earlier with my 2006 PCH trip, I wanted to reassure her, but I knew the challenges that awaited her well, and I too felt uneasy.

Hearst Castle's famous swimming pools enhance the opulent estate.

Meanwhile, Brian, Beatrice, Brad and I were nearing the end of our 2006 trip as we zipped from Big Sur to San Simeon to San Luis Obispo to see Bubble Gum Alley -- it's an alley with thousands of pieces of bubble gum covering the walls. After the thrill of so much chewed gum, we took a leisurely drive down the Malibu coast in our silver BMW and finally reached Venice Beach.

A circle of quirky Venice locals played bongo drums and performed rhythmic dances as the sun set over the Pacific Ocean, smearing the sky with smoggy reds and oranges. My brother Brian and I stood together on the beach, wading in the ocean surf, gazing down the coast at the Santa Monica Ferris wheel and swanky seaside hotels. My old life in Seattle was 1,400 miles away. It would be three years before I visited the Pacific Northwest and my friends there again.

In 2002, my girlfriend and I continued driving north in her red Saab, until at last, Seattle's Space Needle appeared on the horizon. Exhausted, we pulled into the garage of the apartment that now belonged to both of us, and as we began moving her luggage inside, our life transition via Pacific Coast Highway felt complete.

Unbeknownst to us, a Pacific Coast Highway trip that would take me away from my life in Seattle was just four years away.