5-Day San Francisco and Pacific Coast Highway Itinerary

It’s impossible not to have a soft spot for California. The variety in scenery, culture, food, and activities makes the state a paradise for any type of visitor. We’ve visited various parts of California before but for this trip we chose to focus on San Francisco and the stretch of Pacific Coast Highway between San Francisco and San Luis Obispo.

Prior to our vacation, we attempted to research things to do, but we quickly realized there were too many possibilities for this trip. Instead of creating a daily itinerary, we opted to be more spontaneous and just have a list of potential stops. We did have hotel reservations and an adorable Ford Fiesta rented, but other than that we had no specific plans. Thankfully, since we were only cruising down Highway 1 we didn’t have to worry about losing cell service and our access to a GPS. Below is how our trip turned out!

Time of Year: Early September (in an attempt to avoid summer crowds but still enjoy warm weather)

Day 1: Cruising Down to Monterey 

We arrived in San Francisco a little past midnight and spent the night in a seedy motel. The only silver lining was the free continental breakfast and the proximity to the rental car place. Come morning we picked up our rental car and immediately got on the highway heading towards the coast. Our first stop was Half Moon Bay – a charming coastal town with plenty of cute restaurants and cafes to enjoy a meal or snack.

We then continued south and stopped at San Gregorio Beach, a wide sandy beach great for nature photography. It was an overcast day so the park was pretty much deserted. We hiked around a bit and soaked up the coastal breeze. After leaving San Gregorio, we ended up at Pescadero Beach. This beach was also deserted and its rocky shore was a nice contrast to San Gregorio Beach.

Continuing south we arrived at our first large town, Santa Cruz. There we decided to spend our time on the Boardwalk and enjoy the afternoon indulging in a quintessential American boardwalk experience. This boardwalk is fun for all ages with classic games, family-friendly rides and tons of food options. It’s also beachside so you can get away from the abundance of colors and lights if you wish.

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Afterwards, we headed to Point Lobos State Reserve, the famed nature reserve with multiple trail options for hiking. We unfortunately only had time for a couple of the hikes but the views of the rocky coast were stunning.

Side note: In our excitement to explore, we accidentally turned the car engine off before switching to ‘Park’. When we returned to the car and tried to back out, the car lurched forward and we almost rolled off a cliff. PSA to all you eager beavers out there to take your time (and to probably not let me drive).

After a long but fantastic day, we finally checked in to our hotel in Monterey. We figured Monterey was a good base for exploring the area – even if we wandered too far south it was fairly easy to work our way back to the famed coastal town.

Day 2: Big Sur

Today was Big Sur Day! We headed out early so we could spend as much time as possible exploring the famous coastal area between Monterey and San Simeon. This day was extremely foggy which made for interesting driving and even more interesting scenery. Driving Big Sir can be intimidating with its narrow and winding cliffside roads so adding fog to the mix was another layer of stress (or fun depending on how you look at it).

Notable morning stops included Garapata State Park, with coastal hikes, and Bixby Bridge, the bridge in a million photos and commercials. Fun side note – with all our stops we got a bee trapped in the car and spent a solid 15 minutes trying to coax it out. I think our Ford Fiesta deserves a special shoutout for surviving this trip.

We made several other stops that weren’t ‘real stops’ but just looked like interesting places to wander. That’s the beauty of Big Sur, you let your gut tell you where to stop and you’ll likely find something amazing.

We eventually reached San Simeon for lunch before heading to Hearst Castle. At this point, I want to say this castle is LEGIT; it was absolutely stunning and massive. The castle’s creator, William Hearst, kept the best artifacts in his home and he hosted the best company. The man hosted celebrities and politicians like Charlie Chaplin, Cary Grant, and Winston Churchill. He also had the largest private zoo of anyone at the time. Basically he was living his dream life and this castle definitely showed it. Now if you’re European the home might not seem magnificent but to find a castle in California was pretty amazing.

Next we visited Elephant Seal Vista Point where you guessed it – we see A LOT of seals (it was spectacular). Seals were sleeping, swimming, fighting and overall living their best lives. After staring at them for way too long, we headed back north towards Monterey. We continued making miscellaneous stops, the most notable of which was Julia Pfeiffer Burns State Park, which has the famed waterfall you’ve definitely seen on Instagram. We then caught the sunset at Carmel Beach and got a late dinner at one of Carmel’s mediterranean restaurants.

Day 3: San Francisco

We sadly left Monterey and headed back north towards San Francisco. Along the way we made any stops we had previously missed including Big Basin Redwood State Beach (where we watched the surfers), Pigeon Point Lighthouse, and most importantly Pie Ranch. Oh yes, there was a ranch that also had a specialty pie shop and were huge advocates for food education. Amazing.

We arrived in San Francisco and grabbed lunch in the Mission District, the trendy (gentrified) neighborhood. We then headed to Golden Gate Park where we walked around and enjoyed some quality people watching. The park is massive and has multiple gardens and attractions to explore. Next, we drove to the Golden Gate National Recreation Area and Marin Headlands for views of the Golden Gate Bridge and of the city. Traffic to the lookout areas were brutal so if anyone has suggestions for avoiding the cars please let us know!

Day 4: Napa

Most of our fourth day was spent in the Napa Valley. In an attempt to beat the crowds, we woke early and headed straight to Napa. In Napa Valley we did one winery tour at Castello di Amorosa. Many people (snobs) will say this a more touristy winery but since it was our first time in Napa, it was perfect for us! Also, we learned that it was built to resemble an Italian castle so the architecture and decor was stunning. They even have a dungeon which is pretty hilarious.

We did a picnic lunch at a different winery and then headed to the actual town of Napa for some shopping and exploring. We also visited the Oxbow Public Market where we encountered sensory overload with all the great food options. We spent the rest of our time driving around the valley before heading back to San Francisco. Our evening was spent exploring San Francisco’s Chinatown and downtown on foot.

Day 5: Goodbye California

Sadly this was the last day of our vacation. We spent the morning at Fisherman’s Wharf (where we saw more seals!!) and ended our trip with more shopping and eating. 🙂

This was a jam-packed trip but it still felt like we missed a lot! Special thank you to all of our lovely California friends who took the time to meet up with us and give us great suggestions! Let us know what other things we should check out the next time we’re in the area!

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