Many say the planning stage is the best part of a vacation, and for a while, I agreed. It’s a time filled with hope and idealism, imagining the fun ahead, only for the realities and stresses of travel to sometimes turn a dream vacation into a nightmare. So, you can imagine my surprise when planning a trip left me so drained and stressed that I nearly gave up before booking a hotel.
The plan was straightforward: my college friend Imani and I would drive down the California coast for a week after attending our five-year reunion. But soon after I started looking into flights, I realized the words “simple” and “vacation planning” rarely belong together. Choosing destinations, securing affordable one-way flights, picking a rental car company, and sorting through endless hotel options fried my brain.
I was hit hard by decision fatigue, even though I had barely begun the planning. The only solution was to ask for help. Surprisingly, I didn’t turn to Imani, my travel buddy—a logical choice in hindsight—but instead reached out to Visit California, the state’s tourism board. Taking a leap of faith, I contacted a representative I knew for suggestions on activities and accommodations, and this led to an amazing trip with minimal hassle.
What started as a stressful ordeal turned into a luxurious planning process. All I had to do was approve or reject activities, confident that anything the tourism board endorsed would be enjoyable. And enjoyable it was. Our coastal tour was such a blast that even the travel bumps—like three-hour delays or finding a closed tea shop—couldn’t dampen our spirits. Once our trip began, it turned into one of the most stress-free vacations I’d had in a while.
After months of anticipation and a long travel day worsened by a 90-minute wait for our rental car, Imani and I eagerly explored San Francisco. Our plans for the next few days were delightfully flexible, with just three must-visits: Ghirardelli Square for sundaes, Pier 39 for the VIP experience (including a bay tour), and the San Francisco Museum of Modern Art. Otherwise, we were free to explore and catch up with our friend, Kisha.
Having Kisha in town was perfect for our loosely planned days. She always shares great recommendations and comes with detailed lists of her favorite spots. With her guidance, we enjoyed relaxing activities like indulging in excellent tacos from Taqueria Vallarta before unwinding in a park or hiking to a lookout while savoring ice cream.
On our own, Imani and I dove into touristy experiences, and to my surprise, I loved them. Thanks to our Pier 39 tickets, we explored the Fisherman’s Wharf area—a spot I typically avoid due to its popularity. Despite my initial reluctance, the ferry tour was a highlight. We soaked in breathtaking views of the Golden Gate Bridge and Alcatraz and learned a lot about the city’s history—a highlight I would’ve missed if I’d done all the planning myself.
Our two days in San Francisco went by quickly, and it was time to hit the road. I expected Highway 1 to offer great views, but I wasn’t prepared for the sheer beauty of the California Coast. From cliffside beaches to fields nestled beneath mountains, everything was stunning. We could’ve spent a day leisurely driving Highway 1, visiting secluded beaches and sampling fresh cherries and strawberries from roadside stands.
But our schedule kept us moving to places like Rise + Roam, a cozy cafe and restaurant. After enjoying delicious Roman-style pizza, we had extra time before checking into the Cypress Inn. Thankfully, our itinerary included recommended activities and shops, leading us to Point Lobos State Natural Reserve.
I’m rarely at a loss for words, but the beauty of Point Lobos left me speechless. With its cliffs, clear blue waters, and abundant vegetation, it was exactly the stunning vista I’d hoped for. We were so absorbed in the scenery that two hours flew by, making us almost late for our next activity: a wine tasting at Kori Wines.
The Kori tasting room is quaint and tucked away in Carmel. We enjoyed a relaxed tasting of seven wines, starting with a delightful blanc de blancs and ending with a cabernet sauvignon. The quantity of wine was too much for me, so I passed my glasses to Imani, who savored them with ease.
Before we knew it, the two-hour tasting was done, and all that was left for the day was dinner at Vesuvio, an upscale Italian restaurant. After a long day of eating, drinking, and walking, staying awake at the table was a challenge.
The following day marked the end of our time in Carmel, starting with a quick breakfast at Stationaery—I highly recommend the French toast—before heading to San Luis Obispo County. Unfortunately, the planned restaurant visit was thwarted by a day closure, leaving us in a square under the sweltering sun.
With no backup plan, we found a cafe to grab a bite and verify the remaining day’s plans, ensuring no more surprises. Thankfully, the winery visit that followed erased the previous inconvenience. At Booker Vineyard, which welcomed us 30 minutes early, we were treated to sparkling wine and a tour before entering a beautifully appointed tasting room with panoramic views of Paso Robles.
The friendly staff felt like new friends as we savored wines and the stunning views. While the Kori tasting was casual, Booker offered a luxurious experience without pretension. Imani and I spent hours enjoying this moment, thinking, “Wow, I can’t believe this is my life.”
Reluctant to leave Booker but tempted by happy hour and dinner at Hotel SLO, a day of wine and excellent food led me to order a salad instead of the steak I craved. Luckily, Imani thoroughly enjoyed hers.
With another day of indulging behind us, we faced the end of our itinerary. After a leisurely breakfast at Lido Restaurant & Lounge, where I had the tastiest lobster roll, Imani and I were on our own. Our drive to L.A.—with a Sacramento pit stop for ice cream and fries—was uneventful until we faced an unfortunate truth: we had no plans in L.A.
Prior to the trip, we assumed L.A.’s vastness would offer easy solutions, but faced with endless choices after a week of travel, we felt paralyzed and overwhelmed. We returned to old habits, combing through articles and menus.
Our results were mixed: while hiking to the Hollywood sign seemed thrilling, it merely reminded us of Point Lobos’ serene beauty. The Grove, expected to keep us entertained for hours, was disappointing. However, brunch at Lady Byrd Cafe’s greenhouse and relaxing on Malibu’s state beaches provided joy. Compared to the rest of the trip, L.A. was a slight letdown.
Nevertheless, it reinforced my growing belief: travel agents might be onto something. Having a professional handle the planning alleviated most of my stress and let me focus on the fun. In hindsight, trusting someone with my vacation was a bit daunting, but the enjoyment was worth it and far better than if I’d done everything on my own.
