I was dipping a paddle through the Bolinas Lagoon when the gray blob caught my eye. A moment later, it disappeared under the water. Then I noticed other such blobs: a group of seals, keeping a watchful eye and distance from the kayak. Okay, I thought, ChatGPT picked a wonderful way to cap this weekend.
As a new resident of San Francisco, I’ve been eager to take more weekend trips and explore the rest of California. So, given the non-stop barrage of news around generative AI, I wondered: Could ChatGPT act as my travel planner?
At my editor’s suggestion, I settled on a trip to Bolinas, a small coastal community located about an hour north of San Francisco. (I did also ask the chatbot to pick a destination as well, just to see what the query would pull up. It suggested Napa Valley, Lake Tahoe, Monterey, Santa Cruz, and Mendocino. All reasonable enough suggestions, but I was sticking with Bolinas. My editor would be able to compare the ChatGPT itinerary of Bolinas compared to his own recommendations for a trip there.)
To start, I asked ChatGPT to plan an itinerary for a two-day trip to Bolinas, California, in early June. It suggested a rough outline, but was scant on details. For example, I was told to visit “one of Bolinas’ local seafood restaurants,” but no specific establishment was named. The chatbot did, however, call out some specific hiking trails along the nearby Point Reyes National Seashore.
It took a few tries, and I had to get increasingly specific with my prompts—for example, making sure the chatbot knew to give me an afternoon arrival on Saturday (as I knew local hotels didn’t allow check-in before 3 p.m.), and ensuring I would be on the road back to San Francisco before it got too dark on Sunday—but finally ChatGPT gave me a plan, complete with suggestions for restaurants, lodging, and activities, and even a Spotify playlist (think: California-themed songs, classic rock, and “Ride” by Lana Del Ray).
And with that, the trip was officially set.
Saturday
ChatGPT had me kick off my day by driving straight to Bolinas with an 11 a.m. arrival. I was to start the vacation with breakfast at one of two suggestions: the Coast Cafe or the Bolinas Baking Company.
But already I was off to a rough start.
I had cheated and eaten prior to arrival, because 11 a.m. seemed too late for my first meal of the day. Because I wasn’t hungry by the time I got to Bolinas, I switched the first two items on the agenda: ChatGPT said to eat a meal at 11 a.m. and then go see the beach, and I instead opted for a beach session before getting some lunch.
I went straight to exploring Bolinas Beach, where I was supposed to take a “leisurely walk along the shore or relax on the sandy beach.” The beach, as it turns out, is relatively short, so it was a quick walk. Still, dozens of surfers were out in the water trying to catch waves and entertain beach-bound onlookers, and it was nice to grab a seat and watch for a bit.
I then grabbed lunch in the early afternoon at the Coast Cafe. The restaurant was filled with visitors and had a wide-ranging menu, which I took as a win for ChatGPT.
After hanging out by the water for a while longer after lunch, it was now time to check in to the hotel. ChatGPT said to settle in at the hotel but offered no other plans until dinner. I wasn’t sure if I was supposed to just sit in my hotel room; I ended up taking a quick run and then reading for a while in my room.
Eventually, it was dinner time and my choices, per ChatGPT were the Coast Cafe or Wharf Road Restaurant & Bar. Because ChatGPT gave me two suggestions, it made sense to go with the latter, as I’d already eaten at the former. But there was a problem: I couldn’t find any record of Wharf Road. It wasn’t on Google or my phone’s mapping system. It wasn’t in the hotel’s binder full of recommended restaurants to visit, either.
ChatGPT has a knowledge cutoff of 2021, which means the AI is going to miss out on restaurant closures and openings. (Also, it has been known to sometimes provide false information.) Perhaps that accounted for the chatbot’s mention of this phantom restaurant?
Interestingly, there was a nearby restaurant eleven wharf. Though trendy-looking and highly rated, that establishment didn’t receive any love from the chatbot. Considering it’s apparently known as one of Bolinas’ few restaurants, it seems like it should’ve made the list.
ChatGPT again didn’t recommend anything to do after dinner (kind of a shame, considering my lodgings were located directly next to a saloon that’s apparently been open since 1851). I packed it in for the night, falling asleep to the sounds of music playing and people chatting a few yards away from my window.
Sunday
I got up around 9 a.m., packed up, and continued reading my book in the room. ChatGPT had suggested that I start my Sunday with breakfast at my hotel (which wasn’t an option) or at a “local cafe.” But I had to check out of my hotel by 11 a.m., and the recommended post-breakfast activity didn’t open until noon, so I wanted to time out the meal and checkout correctly. Since it had given me two breakfast spots for my first day, I figured I’d choose the one I hadn’t gone to: Bolinas Baking Company. But, again, I couldn’t find any proof that such a place exists. That meant it was time for yet another bite at the Coast Cafe.
The itinerary put the Bolinas Museum up next on the list, which is just a few steps from the Cafe. The museum had several separate small buildings connected through a courtyard, and it only took about an hour to get through. But it was a nice experience, with art and a wealth of history from the region.
ChatGPT then said it was time for lunch. Considering it was only about 90 minutes after having a large breakfast, I wasn’t in the mood again to visit the Coast Cafe or hit up a grocery store to put something together (both of which the bot suggested). I ended up grabbing a coffee from a cafe a few blocks away from the hotel and made out for my next stop: the Bolinas Lagoon.
ChatGPT gave two options for the lagoon: I could take a leisurely walk (something that the AI system seems to really love) or rent a kayak to explore. Kayaking seemed like the move, since I had already done a good amount of walking. ChatGPT didn’t recommend a specific kayak rental outfit, but it was relatively simple to search “Bolinas Lagoon kayak rentals” and find a place with boats for rent.
I plugged in the Spotify playlist and took a short drive to pick up the kayak. But it was all worth it: Kayaking along the quiet lagoon, surrounded by hills and seals dipping their heads in and out of the water, for more than an hour made up for everything.
Overall, the platform suggested a decent itinerary, and upon reflection I should have thought to tell the bot what specific activities I like doing. But it missed on filling in empty spaces in time; it could have easily added items on the agenda that relate specifically to the area. It also lagged when it came to finding places to eat. But given how new the tech is and how much promise it’s already shown (travel organizations including Expedia are already starting to use chatbots to help consumers plan their outings), it’s clear this could be a winning travel aide.
Eventually, it was time to head back to San Francisco. Considering I skipped lunch and spent 75 minutes kayaking, I was more than ready for an early dinner. I plugged in the last restaurant ChatGPT wanted me to visit in the nearby town of Olema, only to discover it was permanently closed.
Well, I’ll always have the seals.
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