San Jose

The drive from Yosemite was far less stressful than the drive to it, and we made it to our San Jose airbnb in pretty good time. A year earlier when I first met Sean, I asked him if he could go anywhere in the world where would he go? He said San Jose, an answer which left me confused. San Jose isn’t exactly known for its tourism industry. I’d never spent any time in it apart from the occasional layover in their airport. Sean explained that as a computer sciences and web development nerd he was interested in seeing Silicon Valley. To each their own, I guess.

Don’t get me wrong, San Jose is a perfectly nice city. It was probably the cleanest and richest city of all the cities we stopped at during the trip. It wouldn’t be a bad place to live. There’s just not a whole lot to do there for the typical tourist. Luckily I was able to talk Sean down from his original ten nights there to a more reasonable five, allowing more time at other cities on our trip. That still didn’t keep people from asking why we were stopping in San Jose at all when I explained the trip to them.

In the end it was actually really nice that there wasn’t much to do in San Jose. We were halfway into our trip at that point and enjoyed having time to relax, sleep in, and take it slow. Our first night in San Jose the boys went to the grocery store and found some frozen White Castle burgers. They had been dying to go to White Castle ever since they saw the movie Harold and Kumar go to White Castle (called Harold and Kumar get the Munchies in the UK). So they were disappointed when they found out that there aren’t any White Castles on the west coast of the United States; it’s more of an east coast thing. That’s why they were more than excited to discover the frozen sliders, and that night we watched Harold and Kumar while eating White Castle burgers, a definite high point in James’ life.

White Castle Sliders

The next morning we decided to explore Willow Glenn, the area our airbnb was in and the so-called “hipster” area of San Jose. James was desperate to get a haircut and he had set up an appointment at one of the barbershops on the main street. We walked around for a bit before the appointment and found a BevMo—a shop with almost every kind of alcohol imaginable—that we decided we would have to come back to later. We stopped at a cafe and grabbed some food before James headed off to get his haircut and I decided to get a pedicure at the nail salon next door. I wasn’t able to convince Sean to go in with me. He claimed it was too expensive (true) and that his toes were too gross from camping (nobody cares) and so he walked around and explored more of Willow Glenn on his own.

After James and I were done we went into a thrift shop, where Sean bought a vinyl record of Lionel Richie’s album Can’t Slow Down. We stopped at Starbucks before heading back to the house and rounded out the day by going to a nearby laundromat and cleaning all our dirty camping clothes.

Lionel Richie

Our airbnb was similar to a mother-in-law apartment, built out of a large shed in the owner’s backyard. We had access to the whole backyard, which had plenty of outdoor seating and a large trampoline. James gave himself a workout by doing front and back flips on the trampoline. But the best part of our stay there was a stray cat who hung out in the backyard with us. It was skittish and shy at first, but James bonded with it and took to calling it Noddy. He fed it little bits of Sean’s turkey meat and was disappointed when I said we couldn’t take Noddy with us. I hope the next airbnb tenants were as nice to it as we were.

The next day we explored more of downtown San Jose and went to the Tech Museum of Innovation. It was cool, but more like a science center than we were expecting, and like most science centers it was geared a bit more toward kids. Still, we enjoyed building robots and doing a lot of the hands-on challenges and activities.

After we were done in the museum we went to Johnny Rockets for lunch, which is a classic American 50’s style diner chain. The decor was all red and white, the wait-staff were all in 50’s style uniforms and there was a small jukebox on every table with your pick of classic rock and roll. We all enjoyed our burgers and milkshakes there, and they still give you the milkshake tin. Then we chilled out in a park before heading back to our airbnb.


The next day was our busiest in San Jose and it was one of my favorite days of the trip. We drove down into Big Sur, which is a beautiful and wild region of California’s coast that serves as a popular spot for camping and hiking and just being out in nature. The highway runs along some cliffs that overlook the ocean and the view is incredible.

We went to Pfeiffer Beach, which might be my new favorite beach, despite it being a bit chilly and windy the day we went. You have to go down a ridiculously narrow and windy one lane road and then pay to park there, but it is well worth it for this beautiful little hidden gem of a beach. We brought our cooler with us, full of drinks we had bought at BevMo, and our camping chairs and it was perfect.

On our way back up the coast we stopped by Bixby Bridge and got some photos. It was built in 1932 and is one of the most photographed bridges in California due to its aesthetic beauty.

Then instead of heading all the way back to San Jose, we went to Santa Cruz. We had tickets to see the band Citizen there that night, who both Sean and I are fans of. In Santa Cruz we ate at a popular spot called Pizza My Heart, which had a line going out the door. The slices were large and delicious, and it was easy to see why it is a Santa Cruz favorite. We grabbed some drinks at a bar called Blue Lagoon before heading over to the Catalyst. It was a small venue, which I love, and we really enjoyed one of the openers, Oso Oso. Citizen were amazing, of course, and even James said he loved it, despite not knowing the band before the show. After the concert we went back to Blue Lagoon and played some pool, before heading back up to San Jose.


We started our last day in San Jose by going to the Winchester House. The Winchester House is a giant and confusing mansion built by Sarah Winchester, the widow of William Winchester, who made a fortune selling firearms. After the death of her husband and their only child Sarah visited a fortune teller in her grief. The fortune teller told her that she was haunted by the ghosts of all the people who had been killed by Winchester rifles, and that she should move west and build a house that is always under construction. The banging and construction sounds would keep the ghosts at bay.

Winchester House Sign

Well Sarah had more than enough money to accomplish this task since she inherited more than fifty percent of her husbands company, and had an income of $1,000 a day, equivalent to $25,000 a day today. Construction started in 1884 and continued until her death in 1922, resulting in the 160 rooms which exist today. It is like a confusing labyrinth inside, and there are many oddities, like staircases and doors that go nowhere, and chandeliers with thirteen candles.

Winchester House

I had read about the Winchester House as a child and always wanted to visit it, so I probably enjoyed the tour a bit more than the boys, but I think it piqued their curiosity as well. Unfortunately we weren’t allowed to take any photos of the inside of the building.

We grabbed lunch at the Winchester gift shop, and then we dropped James off at the gym so he could work out. Sean and I went to see the Apple campus. We weren’t able to go inside any of the main buildings, but we did get to check out the Apple store and the Apple Park Visitor Center. They had a 3D model of the campus enhanced with virtual reality so that you could take the roofs off buildings and see what was inside.

While we waited for James to finish, we went into a grocery store and Sean bought some Ding Dongs just because he thought the name was hilarious. That night we drove back up to San Francisco and briefly visited with Erin before giving her our camping gear to store for us so that we would have room for Glenn when he joined us in Santa Barbara a couple days later. Huge shoutout to Chandini and Erin for helping us out!

Want more? Read about our next set of adventures in Santa Barbara!

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