About this Trip
We found a cheap flight on Southwest Airlines from Dallas to San Jose over a four-day school holiday with the kids. Dallas had a "heat dome summer" which is about as fun as it sounds and lasted what felt like an eternity. We thought that going to Northern California in October would be nice and cool. Ironically, it was one of the hottest weekends on record in California at 91 degrees and Dallas cooled down to a beautiful 70 degrees. All fine of course; Texans can handle heat. Our big motivator to go to San Jose was to tour the Winchester Mystery House, but San Jose is also a great home base if you want to travel into Santa Cruz, Monterey, San Francisco, or other popular surrounding areas.
We rented a Tesla for two of our 5 days on this trip and took Ubers on the days we stayed in San Jose. In hindsight, I would have liked a car the whole time. Not many places in San Jose were walkable and parking wasn't as bad as I thought it would be.
We stayed at the lovely Signia by Hilton San Jose in a suite which allowed us plenty of space and had a fantastic staff. From the hotel, we could walk to the San Pedro Square Market where we ate dinner almost every night. There was a nearby lot where we could park the car at half the price the hotel wanted to charge ($25 instead of $50).
Day 1 - Winchester Mystery House and Santana Row
We made the Winchester Mystery House our first stop and we were not disappointed. This attraction is popular and does sell out, so we bought our tickets ahead of time and showed up about 40 minutes early. If you're early, you have time to tour the gardens and the gift shop so there is a lot to do while you wait. The mansion tour was really engaging and interesting. Was Sarah Winchester a cursed guilt-ridden woman haunted by spirits of those killed with the Winchester rifle, or a bereaved kind-hearted philanthropist who felt the only way to keep her staff afloat in a tough economic climate was through constant construction? Decide for yourself - the tour will give you both perspectives. Regardless, this eccentric house has doors and stairs that lead nowhere, windows in the floor, and lots of funny little twists and turns. They have other tour options to go into the basement and optional axe throwing packages too. I especially loved seeing it in October. They put a very cute Halloween Museum on the grounds and added spooky touches all around. We didn't see any ghosts though; maybe next time. There is a PG-13 movie called Winchester that you might want to watch before you go; not me though - looks too scary.
After this, we walked over to Santana Row and got ice cream at Smitten.
If it's open, I recommend going to the Rosicrucian Egyptian Museum after the Winchester House. We weren't able to fit it in later in the trip, and in hindsight I wish we had gone this day.
Day 2 - Monterey
We drove to the Monterey Bay Aquarium and we all loved it; parking was no problem (though I read it definitely can be) and we got see the divers feeding the fish too. After the Aquarium, we were close to the Pacific Grove Entrance of the popular 17-mile drive, so we decided to do that. 17-Mile Drive is a scenic road through Pebble Beach and Pacific Grove on the Monterey Peninsula, much of which hugs the Pacific coastline and passes famous golf courses, mansions and scenic attractions. There are many, many good travel guides online that detail exactly where to stop, but the attraction is also well signed and they give you a map when you come in. It costs $11.75 per car.
I can't recommend this highly enough. There are not a lot of places to eat until you get to Pebble Beach. Luckily, we had a lot of snacks with us, but lunch in between the aquarium and 17 mile drive would have been wise. There was a market near the Lone Cypress that sold food, but we ended up wanting to get back to San Jose instead of eating there. Since it was 91 degrees, we assumed that the kids would get their feet in the water on some of the stops. As anyone with kids knows, that means they ended up swimming in the "restless sea" and were completely soaked. We were prepared with towels and extra clothes (this time!) though.
Before you go to Monterey, adults should watch Big Little Lies; we enjoyed playing the moody soundtrack as we took in the coastal views. Children could also give Finding Dory a watch - the Monterey Bay Aquarium was one of the main inspirations for the fictional Marine Life Institute in the movie.
Day 3 - Redwoods and Santa Cruz Boardwalk
We decided to visit Henry Cowell Redwoods State Park in the morning in favor of other optional destinations like Roaring Camp or Big Basin. Henry Cowell is beautiful - the Redwood Grove Loop Trail is only .9 miles and honestly was the prettiest and most interesting part of the park. We also hiked to the Observation Lookout, a moderate/strenuous hike depending on how many times you get lost and how hot it is outside.
After our hike, we had lunch in Santa Cruz on the boardwalk. Parking was a nightmare (bring quarters!) and the place we picked to eat was just okay. We planned to visit the beach after lunch, but one of the boys wasn't feelling well and honestly, the crowds/parking situation was out of control, so we abandoned the plan. We ended up going back to the hotel with it's very nice pool, and then had dinner at San Pedro Market.
Day 4 Kelley Park
Kelley Park has a few other parks within it: The Happy Hollow Park and Zoo, History Park, and the Japanese Friendship Garden. The first one is a little zoo and amusement park. The rides are geared toward the very young, but there was a mini roller coaster that my older son liked well enough, and he loves animals so he had fun. The cost to get into Happy Hollow was about $18 per person. There was a lot of shade and it kept my kids entertained for about 3 hours.
The History Park has a trolley and some historic buildings you can go in and tour (there is also a scavenger hunt you can pick up to keep their interest). There are volunteers in each building who will answer any questions you have and provide some context from the past. My guys love stuff like this, and it was free, so we spent a lot of time here. I had to drag them out of the little school house.
The Japanese friendship garden has most of it's ponds drained when we went, which really detracts from how pretty you can tell it was at one time. It's also free and I hope they are able to fix the water situation soon.
Check the hours of each park carefully - the hours for Kelley Park are pretty much sunrise to sunset, but the other parks were either closed entirely or closed by 4 p.m.
After this, it so happened the Dallas Cowboys were playing the San Francisco 49ers, so we headed to San Pedro Market to watch them play (and lose spectacularly).
Day 5 - Japantown and Intel Museum
Our last day was a Monday - and EVERYTHING was closed. So, we didn't plan this part very well. We should have saved Kelley Park or something for this day and taken more advantage of Sunday to do the Egyptian Museum, Tech Museum, and the Flea Market. But, we had already turned in our car and were flying out later in the day, so we did our best to take advantage of what we could do. Japantown was really nice (but sadly most of the shops were closed). We did get some Japanese snacks to take home on the plane at the grocery and ate delicious sushi at Kazoo Restaurant.
The Intel Museum is free and small, but honestly pretty good considering. I wouldn't make it a primary destination, but if it's nearby other things you are touring, it's a great stop.
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