One of the first trips that really got us hooked on planning detailed itineraries was a road trip through California.
We knew we wanted to visit, but quickly ran into the obvious question… how do you pick just one place in California?
So instead, we didn’t. We planned a trip where we changed hotels almost every night so we could see as much as possible and get a mix of different experiences along the way.
San Francisco – San Diego
This trip was taken July 2019.
Checkout our YouTube video of the whole trip!
This was our first real “move fast and see a lot” road trip. It is absolutely not a relaxing style of travel — but it was exciting, and it completely changed how we plan trips now. We’ve done versions of this itinerary style since, but this was the first time we tried it.
It’s also a fast 7-day route, and we easily could have spent more time in almost every stop. We’ve got a long list of places we missed and want to go back to someday.
- Day 1: Arrive San Francisco 9am (so tired) and explore
- Day 2: Morning in San Francisco then drive to Monterey, making stop near Santa Cruz
- Day 3: Big Sur day, ending in San Luis Obispo
- Day 4: Drive towards Disneyland, making stops at Solvang and Venice Beach
- Day 5: Disneyland
- Day 6: Drive to San Diego, stopping in Laguna Beach and in La Jolla
- Day 7: San Diego Zoo
- Day 8: Leave
Day 1 (lodging – Columbus Motor Inn)
We started in San Francisco after picking up our rental car. Since we arrived before check-in, we used the time to explore a bit.
First stop was Twin Peaks for a full view of the city. Then we drove through the Castro District before heading over to the famous Painted Ladies — which was especially fun for us as longtime Full House fans.
We stayed at the Columbus Motor Inn which ended up being a great fit. It’s a pretty simple hotel, but in San Francisco that balance of price and location is hard to beat. We were able to walk to a lot of places, which made things much easier.
We did a bit of over-research (as you do) and looked at what felt like hundreds of hotels, so we felt pretty good about this choice in the end.
One of the highlights nearby was walking to breakfast at Pat’s Café — simple, but really good..
After checking in, we headed down to the waterfront to catch our tour of Alcatraz Island.
We had booked tickets as soon as they were released since they sell out quickly, and this was one of the main things we were excited for.
The boat ride over was chilly, but it was also one of the best ways to see the city from the water — especially as you pull away and the skyline gets smaller behind you.
Alcatraz Island ended up being one of the most memorable stops of the trip.
The island has this eerie feeling to it that’s hard to explain. Walking through the old prison and stepping into the cells was both fascinating and a little unsettling — the kids were equal parts interested and totally freaked out. The audio tour is excellent too, with real stories that make the place feel surprisingly vivid.
If you’re in San Francisco, this is a must-do.
After we got back, we squeezed in a few classic stops on the walk back to the hotel before calling it an early night. We walked through Pier 39 to see the sea lions, then made our way up to Lombard Street.
Both are busy, touristy stops — but still worth seeing once.
Day 2 (lodging: Holiday Inn Cannery Row)
Before leaving San Francisco, we made one last effort to see the Golden Gate Bridge from a few different angles.
We stopped at three viewpoints:
- Battery East Vista Point — easy parking and a nice park area
- Golden Gate Bridge Vista Point — very crowded, but classic views
- Fort Baker — our favorite by far, with wide open views and far fewer people (plus we even spotted a few sea lions in the water)
Each spot shows the bridge in a slightly different way, so it was worth stopping at all of them.
We grabbed a quick stop at In-N-Out Burger on the way out of the city, then officially started heading down the coast. One of our favorite unexpected stops along the drive was Henry Cowell Redwoods State Park. We did a short, easy 1-mile loop and it was our first real introduction to the redwoods on this trip. Even just that small walk made a big impression — the trees are hard to capture in photos, but you really feel the scale in person.
We would have loved to stay longer, but this was just the beginning. (Spoiler: we end up coming back to California a few years later and see even more!)
By evening, we arrived in Monterey and checked into our hotel right on Cannery Row.
We stayed at Holiday Inn Express Monterey – Cannery Row, which was perfect for being able to walk everywhere that night. The whole area has a really easy, coastal-town feel — super walkable, lots of little shops, and just a nice vibe after a full day of driving.
We had dinner nearby, wandered a bit, and finished the night with ice cream from Ghirardelli Ice Cream & Chocolate Shop before heading back to the hotel.
Simple ending, but one of those nights that just felt easy in the best way.
Day 3 (lodging: Madonna Inn)
We started early with a quick stop at Lover’s Point Park. The Monterey coastline is just stunning — even simple stops like this feel worth it.
From there, we headed to Point Lobos State Natural Reserve, which is absolutely a must-visit. We did a few short trails and honestly could have spent much longer here. The mix of cliffs, coves, and wildlife makes it one of those places where every turn feels like a postcard.
Next up was the main event: Big Sur.
We knew we could have spent days here, but we only had time for a few stops. The highlights were:
- McWay Falls
- Bixby Creek Bridge
- Salmon Creek Falls
Parking at some of these spots was busy and a bit limited, which made it impossible to stop everywhere we wanted. But even just driving through Big Sur is worth it on its own — it’s one of those rare roads where the drive is the experience.
A few tips:
I’m really glad I brought printed maps for this stretch. We marked distances between stops ahead of time because a lot of pull-offs are small, easy to miss, and not always obvious to turn around for.
We also lost cell service in several areas, so having paper directions was genuinely helpful.
Food-wise, we packed PB&J sandwiches and just stopped at scenic pull-offs when we got hungry. There aren’t many food options along this section, and honestly, eating lunch with a cliffside view worked out better anyway.
As we continued south, we stopped at the Piedras Blancas Elephant Seal Rookery.
These animals are massive — and kind of hilarious to watch. Even outside of peak season, it was still fascinating just seeing them up close. I’d love to come back when the colony is at its busiest.
We also made a quick stop to see Morro Rock — a huge volcanic plug rising right out of the water. It’s one of those landmarks that looks almost unreal in person.
That night we stayed in Madonna Inn, and it instantly became one of our favorite hotels ever.
It’s hard to even describe — every room is completely different, over-the-top themed, and full of personality. It’s quirky, a little kitschy, and completely unforgettable.
There’s even a pink basketball court, horses on the property, a beautiful pool, and views of the hills around San Luis Obispo.
We went out for dinner in downtown San Luis Obispo, but honestly rushed back because we just wanted to enjoy the hotel.
Our room had a loft area with a second floor and twin beds, which the kids thought was the best thing ever — basically their own little upstairs hideout.
I still think about this place all the time. It’s one of those stays that just sticks with you.
Day 4 (lodging: Holiday Inn Anaheim)
We set off early for another full driving day along the coast.
First stop was the cute town of Pismo Beach, where we grabbed some absolutely massive cinnamon rolls — the kind you don’t really plan to finish in one sitting, but somehow do anyway.
From there, we continued on to Solvang, a small Danish-style town that honestly feels like a movie set. We picked up a few baked goods for the road and wandered through the little shops for a bit. It’s charming in a very specific, very intentional way.
There’s also an OstrichLand USA nearby that we would have stopped at if we had more time — adding it to the growing list of “next time” stops.
We also made a quick stop at the Channel Islands National Park Visitor Center. It’s a small stop with a few exhibits, and while actually getting out to the islands would take much more time than we had, it worked well as a break and picnic lunch spot along the way.
From there, we kept heading south with a couple of short scenic stops, including a lookout and small beach area before reaching the Los Angeles area.
We drove through Malibu and eventually made it to Venice Beach — at which point we were pretty exhausted from both driving and trying to fit everything in.
The pier area was busy, hot, and honestly a bit overwhelming. It wasn’t really our favorite stop and probably not one we’d prioritize again.
Venice Beach, though, was more fun for us. We had to stop to play a bit of basketball near Venice Beach Basketball Courts and we walked by the Muscle Beach Venice, which was interesting to see in person.
After that, we continued on to Anaheim… and sat in traffic for what felt like forever. A very “real” Southern California ending to a very packed day.
Day 5
Today was all about Disneyland!
This was the main reason we came down to this area in the first place. We really enjoyed it — the kids had a great time, and it was a fun break in the middle of a very busy road trip.
That said, I’m not totally sure we’d structure the trip the same way again. It ended up costing us two nights in Anaheim, and in hindsight we also missed out on more time along the California coast, which we really loved. Having Walt Disney World Resort closer to home also changes the equation a bit for us — it’s bigger, and we tend to lean toward that for a full Disney trip.
Still, as a one-off stop on a longer road trip, it worked well. The kids were happy, we got the classic Disney experience, and it broke up a very driving-heavy stretch of the trip nicely.
One day I’ll put together a full Disney World vs Disneyland breakdown with everything we’ve learned from both — because there are definitely pros and cons to each depending on how you travel.
Day 6 (lodging: Best Western Hacienda)
First stop of the day was Laguna Beach. This town was way more charming than I expected — really relaxed, coastal, and easy to wander through.
We grabbed coffee and mostly stopped so we could play a quick game of basketball at a court right by the beach. Simple stop, but a good way to start the day.
On the drive down toward San Diego, we stopped in La Jolla to see the sea lions.
They were loud, chaotic, and honestly pretty funny to watch. There were also a lot of people right up close to them on the rocks. I didn’t fully research it beforehand, and I know now that getting that close isn’t great for the animals or really safe for visitors either. The photos are cute, but it’s something I’d approach differently in hindsight.
That said, even if you don’t go right up to them, La Jolla still has plenty of viewing areas and is absolutely worth a stop.
Next up was the USS Midway Museum, and this ended up being one of the highlights of the day.
The ship is massive and packed with exhibits. We got to see the captain’s bridge, explore parts of the living quarters, and even climb into some of the aircraft on the deck. At one point, my son was holding the old ship phone used for communications — one of those small moments that stuck with him.
It’s the kind of place that does a really good job of showing just how big and complex a ship like this actually is.
For the night, we stayed at the Best Western Plus Hacienda Hotel Old Town in Old Town San Diego.
This was a great location. The hotel itself was comfortable and had a nice pool, but the best part was being able to walk straight into Old Town for food and wandering in the evenings. It made everything feel easy and low-stress after full days out exploring.
Day 7
The real highlight of San Diego was the next day at the San Diego Zoo. It lives up to the reputation — there’s so much to see, and the kids loved every part of it.
After the zoo, we spent part of the afternoon at Pacific Beach before heading back to Old Town to wrap up the day.
Wrapping Up Southern California
After a packed few days, our Southern California road trip came to an end in San Diego.
It felt like one of those trips where we tried to fit in just one more thing every day — coastal drives, theme parks, cities, beaches — and somehow it all worked together. But by the end, we were definitely ready to slow down a bit.
This route ended up being a mix of everything: big landmarks, small towns we’d never heard of before, long drives with incredible views, and a few stops that were better in person than we ever expected. It was also a reminder that California is just too big to “do it all” in one go — no matter how much you try to plan.
Looking back, Disneyland was fun for the kids, but the coastal drive — especially Big Sur, the redwoods, and the quieter towns — was what we’d probably prioritize again if we did it differently. There’s something about just being on the road, pulling over when something looks interesting, and not overthinking the schedule that really stuck with us.
We left with tired kids, way too many photos, and a long list of places we want to come back to someday (and do a little slower next time).
If you’re planning something similar, I’d say this: don’t try to see everything. Pick a few stretches you really want to experience, leave space in your itinerary, and expect the best parts to be the unplanned stops along the way.
And if you’re curious about the rest of our travels, we’ve shared other road trips through California — plus our next adventures up the coast into Oregon and Washington.
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