California Road Trip: Day 1 in San Jose, Santa Cruz & Monterey

Hi friends!
I hope your Monday is off to a great start! Last weekend we took a drive to Plymouth, MA and walked along the jetty while enjoying the sunshine and salty air. This got me thinking about some of the longer road trips that we’ve taken in different parts of the United States, where we’ve explored and experienced so many adorable coastal cities and towns. There’s been so many good ones. From the Savannah, GA to Charleston, SC route to the Boston, MA to Portland, ME route. Then there was our very favorite California road trip.

Vacations are looking a little different this year due to COVID-19, with many opting for scenic road trips and beach getaways, where social distancing can be practiced a little more easily. I thought sharing our longest road trip along the Pacific Coast Highway in California might help you with your own vacation planning – whether you’re starting that process now, or in the future. I’m someone who loves planning a trip a ways out out, as it gives me something to look forward to!

We took this California road trip almost exactly two years ago (September 2018), following my brother’s wedding in San Martin, California – a tiny little vineyard town just south of San Jose. My brother and sister-in-law planned to leave for their honeymoon immediately following their big day. Since we were already out West, my husband Josh and I decided it was the perfect time to finally drive the iconic PCH. After all, it had been on our bucket list for so many years! 

I’ll be breaking up my summary of this 500-mile trip into six posts. So be on the look-out for a recap of days two through seven, over the course of this week!

As we took this road trip prior to COVID-19, the hotels, restaurants and attractions featured in my posts may not currently be open, or they may be offering limited service. If you use this post to plan your own trip, please verify these important details directly. Also, for those traveling now or planning a getaway in the very near future, please wear a mask to protect the locals and fellow travelers. We’ll get through this pandemic together!

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Day 1: San Jose, Santa Cruz & Monterey

San Jose

The hotel for my brother’s wedding weekend was in San Jose, so this city was our starting point. Otherwise, I’d recommend starting in San Francisco, especially if you’ve never been. If you begin your adventure in San Jose or you make it one of your stops, the San Jose Marriott is a great option. The property was incredibly clean, rooms were a good size, and it’s walking distance to many great restaurants. 

Following breakfast and saying goodbye to our family, our first stop before officially hitting the road was for coffee. Pro tip: do not stay up until the wee hours drinking cocktails the night before a week-long road trip. But hey, my brother married the love of his life and I gained an incredibly awesome sister. That was definitely worth celebrating! Voltaire Coffee House was diagonally across from the San Jose Marriott so we popped in for a couple of cold brew iced coffees. They definitely hit the spot and gave us the extra bit of energy that we needed. And with that, we set off on our California road trip!

Santa Cruz

anta Cruz was our first stop of the day, which was only about 40 minutes south of San Jose. Another pro tip: pack the Dramamine if you’re susceptible to motion sickness. You’ll cut through the Santa Cruz Mountains so driving up peaks, down into valleys and around some twisty turns might leave you feeling a little queasy. Trust me on that one! Parking in Santa Cruz was impossible. We unfortunately couldn’t find a parking spot anywhere. We also spotted many cars with parking tickets, so we ended up taking in this seaside town’s sites from the car as we drove. I’m not big into rides (hello motion sickness!), but the Santa Cruz Beach Boardwalk is pretty impressive. Definitely a must if you have kids in tow. 


Knowing we only planned for about 18 hours in Monterey, we continued driving another 45 minutes south and arrived in this adorable coastal town at about 2:30pm. Our check-in at the Monterey Plaza Hotel & Spa wasn’t until 4pm. However, the front desk staff graciously offered us an early check-in. I can’t say enough great things about this hotel. The staff is incredibly courteous and friendly, the views of the ocean are stunning, and it’s centrally located a block from Cannery Row. The bed was also one of the most comfortable that I’ve ever slept in. Although, I was so tired from the wedding the night before that I probably could have slept peacefully on a bed of hot coals. Ha! We didn’t take advantage, but they also offer complimentary bikes and courtesy Land Rover shuttles. 

After dropping our bags in the room, we explored Cannery Row for a couple of hours. We popped in and out of the many gift shops, art galleries and jewelry stores. We also passed by Coast Guard Pier, which was teeming with sea lions. They were so fun to watch! There’s also a number of wine tasting rooms in Cannery Row, and we loved Carmel Ridge Winery. They had several wine flights to choose from at various price points, and the wine was delicious.

The shores of Monterey, California
The shores of Monterey, California
Josh at Cannery Row, Monterey
Josh at Cannery Row, Monterey
Wine tasting at Carmel Ridge Winery in Monterey. Perfect way to spend the afternoon on day one of our California road trip!
Wine tasting at Carmel Ridge Winery, Monterey

Another favorite was Monterey’s Tasty Olive Bar, which had a huge selection of interesting infused olive oils and vinegars. They were free to sample with the complimentary bread they had set out. Cannery Row is definitely a very touristy area and three hours felt like the right amount of time to explore. If we had more time and had arrived earlier in the day, we may have checked out the Monterey Bay Aquarium, which is one of the most well-known aquariums in the country. After a fun afternoon of strolling and wine tasting, we went back to our hotel room to relax, shower and get ready for dinner. 

We had a reservation at Schooners Coastal Kitchen & Bar, which is inside the Monterey Plaza Hotel & Spa. Although it was a Sunday night, this place was packed! Quite a few people were waiting for tables so I definitely recommend a reservation. The ocean views were gorgeous and the food was amazing. I had the seafood pasta bolognese and Josh had their New York steak. After dinner, we called it an early night and relaxed in the room. After the previous night’s wedding festivities we were definitely ready for some sleep. All in all, I’d say the first day of our California road trip was a successful one!

Schooners Coastal Kitchen & Bar - a great way to end the first day of our California road trip.
Schooners Coastal Kitchen & Bar – such a beautiful view!

Be on the lookout for tomorrow’s post where I share day two of our California road trip. The post will recap all the fun we had along the famous 17-Mile Drive, as well as in Big Sur and Pismo Beach!

As always, please leave any comments or questions below. I love chatting about travel, so always happy to answer your questions about our trip. If you need recommendations I’m also your girl!

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California Road Trip: Day 1 in San Jose, Santa Cruz & Monterey