I Had Experts Help Me Plan the Perfect California Road Trip

I've heard that the planning stage is the best part of a vacation. For a long time, I believed that. There's so much hope and idealism in the planning process where the only thoughts are of how fun the trip will be, just for the reality of life and stresses of travel to turn that best-ever vacation into a nightmare. So imagine my surprise when planning a vacation left me exhausted and so stressed that I was tempted to call it quits before even booking the hotel room.

My vacation plans were simple enough: my friend from college, Imani, and I would spend a week driving down the California coast after swinging by our five-year reunion. But as soon as I started researching flights, I realized that the words "simple" and "vacation planning" do not belong in the same sentence. After deciding on the stops, finding three one-way tickets that wouldn't break the bank, choosing a rental car company, and sifting through hundreds of hotels across four cities to narrow options, my brain was fried.

Decision fatigue hit me hard, and I barely started the planning process. The only solution was to ask for help. Not from my travel buddy (which, in hindsight, was the most reasonable option), but from Visit California, the state's tourism board. Taking what felt like a huge risk, I reached out to a rep I knew for some suggestions on things to do and where to stay and, in return, got to enjoy a trip of my dreams with minimal decision-making.

The planning process transformed from stress-inducing to luxurious. All I had to do was approve or deny activities, and I felt confident that if the tourism board was promoting the business, I was sure to enjoy myself. And enjoy myself I did. The week-long tour down the coast was so much fun that even the hiccups of travel—like three-hour delays or finding out the tea shop we were scheduled to visit was closed all day—didn't kill the mood. After the trip started, it was one of the least stressful vacations I'd had in a while.

San Francisco

After months of anticipation and a long day of travel made even longer by a 90-minute wait to get our rental car, Imani and I couldn't wait to get out and see San Francisco. Our plans for the next few days were nebulous in the best way. Imani and I had only three required stops: Ghirardelli Square for sundaes, Pier 39 for the VIP experience (which included a bay tour), and the San Francisco Museum of Modern Art. Other than that, we were on our own to explore and reunite with our friend, Kisha.

Having a friend in town was perfect for our minimally-planned days, especially a friend like Kisha, who always has the best recommendations and is generous enough to give detailed lists of her favorite spots. With Kisha, we enjoyed lowkey activities like getting truly excellent tacos from Taqueria Vallarta before relaxing in a park or hiking to a lookout while eating ice cream.

On our own, Imani and I had more touristy experiences, but I was shocked at how much I enjoyed myself. If not for the tickets for Pier 39, I'd never have considered the Fisherman's Wharf area because I'm often one of those "avoid the popular tourist spots at all costs" types. But despite my snobbiness, the hour-long ferry tour was one of my highlights. We were treated to incomparable views of the Golden Gate Bridge and Alcatraz and learned so much about the city's history. That tour was a highlight I would've missed if I had been wholly in charge of planning.

Driving the Central Coast

Our two days in San Francisco sped by, and it was finally time to start the road trip. I knew that Highway 1 would treat us to some great views, but I still wasn’t prepared for the beauty of the California Coast. Everything was beautiful, whether it was a cliffside beach or agricultural fields in the shadow of a mountain. We could’ve easily spent a day moseying down Highway 1, stopping at those seemingly empty beaches and sampling fresh cherries and strawberries from the roadside vendors.

But we had places to be. Specifically, a little cafe and restaurant called Rise + Roam. After wolfing down a truly delicious Roman-style pizza, we had some time to kill before we could check in at the Cypress Inn. And thankfully, our itinerary included a range of recommended activities and stores to shop at, which is how we made our way to Point Lobos State Natural Reserve. 

It’s a rare moment that I’m at a loss for words, but there aren’t any that can express how gorgeous Point Lobos is. It was exactly what I was hoping for, a stunning vista with cliffs, clear blue water, and plenty of vegetation. There was so much beauty to soak in that two hours passed in a flash, and we were suddenly running late for check-in and our next activity: a wine tasting at Kori Wines.

The Kori satellite tasting room is a compact store in a charming corner of Carmel. The tasting was a casual affair, taking us through seven wines, starting with a delicious blanc de blancs and ending with a cabernet sauvignon. It ended up being far too much wine for me, and by the time we got to the reds, I was handing my glasses to Imani, who finished them like a champ.

Before we knew it, the two-hour tasting was over, and the only thing left for the day was dinner at  Vesuvio, a tasty restaurant serving upscale Italian fare. The long day of eating, drinking, and walking meant it took all my effort not to doze at the table. 

The following day marked the end of our time in Carmel with a quick breakfast at Stationaery (I highly recommend the French toast) before we were off to San Luis Obispo county.

Unfortunately, the restaurant we were scheduled to visit was closed for the day—leaving us standing in a shade-less square on a 100-degree day in a town where more than a few businesses were also shuttered. Without any backup options on hand, we found a promising cafe to grab a bite while we verified the rest of the day’s plans and made sure there were no more surprises.

Despite the negative turn of events, the winery we visited next was so incredible that the minor hiccup was forgotten. When we got to Booker Vineyard, which let us begin our tasting 30 minutes early, Imani and I were greeted with a glass of sparkling wine and immediately got a tour of the vineyard and tasting rooms. After the tour, Imani and I were placed in a gorgeously appointed tasting room with floor-to-ceiling glass windows on three walls showing off the rolling hills of Paso Robles.

Every staff member we met was so friendly it felt like we were sipping wine with new friends instead of attending a formal tasting. If the tasting at Kori was chill and casual, then the tasting at Booker was luxurious without being pretentious. Imani and I spent hours savoring the wines and the views, thinking, "Wow, I can’t believe this is my life."

The tasting at Booker was so enjoyable we didn’t want to leave, but happy hour and dinner at Hotel SLO were calling. A day of red wine and plenty of good food meant I had to order a salad at the steakhouse Ox + Anchor, but while I couldn't enjoy the steak I was dreaming of, Imani strongly endorsed hers.

Los Angeles

After another long day of drinking and eating, our itinerary was, sadly, nearing its end. After a leisurely breakfast at Lido Restaurant & Lounge, where I had the most delicious lobster roll I'd ever eaten, Imani and I were on our own. The drive to L.A.—with a pit stop in Sacramento for ice cream and French fries—was generally uneventful, but as soon as we got into the city limits, we realized an unfortunate truth: we had no plans in L.A.

Of course, we knew this before the trip started and assumed that because the city is so massive, it would be simple to fill our days. But being confronted with endless possibilities after a week of travel just left us paralyzed and overwhelmed. It was back to old habits of trawling articles and comparing menus to find something to do and someplace to eat.

Our results varied: a hike to the Hollywood sign sounded like a fantastic idea, but the dusty trails and crisp vegetation just made us miss the serene beauty of Point Lobos. A visit to mega-complex The Grove was supposed to keep us entertained for hours, but that plan didn't pan out. On the other hand, we did have a fantastic time eating brunch in a tiny greenhouse at Lady Byrd Cafe, and lounging on the state beaches of Malibu was the perfect way to pass the time. If it hadn't come after an almost perfect four days of California travel, our time in Los Angeles would have been perfectly fine, but compared to the rest of the trip? It was a bit of a letdown.

Still, it confirmed what I was beginning to suspect: those who swear by travel agents for their vacations might be onto something. Handing the reins to a professional took away most of my planning anxiety and let me focus entirely on the fun. And while trusting another person with my vacation was scary, I doubt I would've had as good a time if I had done it all on my own.