Planning a California Family Road Trip

Tall palm trees swaying in the breeze, sipping wine amongst the vines in wine country, seeing which hand prints closely resembled mine outside the Chinese Theater in Hollywood. These were all the things (and more I wanted to do in California). Today, I’m sharing a little about planning a California family road trip.

That was Big Sur! Yup. It was kind of foggy the day we drove it but, man was it beautiful!

I can’t believe it’s been a month since I last blogged. Did you guys miss me?!?

If you didn’t know already, or if you’re new around here, Mr. Silver Pennies, my hubby Luke, got a sabbatical from his work. Every 5 years at his company, employees get a month off and money toward a trip. We’ve always dreamed of a trip to the Golden State. We decided to book a three week road trip, giving Luke a little less than a week when he got back to relax poolside. You may remember we just finished the pool house before went.

I’m currently going through all the photos from the trip. I took hundreds and hundreds of photos. I’m still editing some. I brought my Nikon camera but also took some along the way with my phone. So if you came across some on Facebook or Instagram, those were all ones I took with my phone. Sometimes it was just easier to bring a phone places, like Universal.

I have so much to share with you guys. We had the most amazing time, met the nicest people, and got to catch up with a lot of friends while we were out there. Even more important than that, we got to spend three whole weeks with our two boys, discovering amazing sites and also being completely IN the moment. We didn’t bring our computers and Luke had to switch his work emails off. I put an out of office reply on my blog emails and I’m so happy I did.

John and Conor are growing up so quickly. I know these times of family trips and vacations are fleeting. In just five years John will be off to college. This is the trip I know we’ll always remember with so much happiness.

On this trip we were able to slow down; see the beauty in wild flowers, search for moonstones on Moonstone Beach, see the bobbing heads of sea lions amidst the seaweed in Monterey. It made me realize just how scheduled and hectic our daily lives are here at home. We’re controlled by our technology (always trying to keep up with social media, news, and posts), we’re running errands and checking things off our list. This family road trip made me realize a less hectic pace would be better for all of us. Now, that we’re home we’re trying to be on our phones less and plan on family runs and bike rides.

I’m digressing, through, as I want to share our process for planning this trip. I’ve received quite a few questions from readers and friends who are planning the same trip and I want to be able to share EVERYTHING we did and maybe some things we wouldn’t do again.

Where Did We Go?

We started in San Diego and spent two nights there. Then we drove to Hollywood on the third day, stopping in Newport Beach for stroll and ice cream. Oh, and to see Serena & Lily!

4 Nights in LA to explore all the famous landmarks and to take the boys to their first big amusement park – Universal Studios.

One night in Solvang (where they filmed Side Ways) and we sipped the Hitching Post II wine with flatbreads and a charcuterie board. We had a few days to explore the Central Coast – Santa Barbara, San Simeon, Cambria. A whole day dedicated to driving and exploring Big Sur. Two nights in Monterey, and one night on the outskirts of Santa Cruz.

There was lots we wanted to see in San Francisco so we spent three nights there. Finally, we ended our trip with an extra long period in Wine Country. We had five nights to explore, taste wine, see friends, and relax.

Tips for Planning a California Family Road Trip

• Determine where you want to go. I know this sounds so easy but it’s a bit more complicated when you consider how big a state California is. We had 3 weeks, but had to figure out where we wanted to go in those three weeks. The first thing we did was talk to family and friends who either live in California or have visited and asked, “What do you think we NEED to see?” I would type in my Keep app on my phone EVERY suggestion. I also included things people said we shouldn’t do. I need to write everything down or I’ll forget it completely.
• Book Flights when they are the cheapest. Flights are usually the cheapest 6-9 weeks ahead. So we waited to book our accommodation until the flights were secured.
• Shop around for car rentals. We found renting a car in San Diego off-airport made the price drop in half, which is significant when you’re going for a long time.
• Should you do AirBnB or Hotels? We LOVE AirBnB and have had great experiences in London and Vermont in them BUT for this kind of trip we found that hotels worked better for our family. Most AirBnB were going to charge cleaning fees which would be very expensive if we were only staying one or two nights. Also, all the hotels we stayed at had parking which comes in handy in cities, like LA and San Francisco. We did have to pay additional for parking but just knowing we had a safe place to park the car was reassuring. Be aware of resort fees that can be added onto the price of the hotel.
• How to get the best hotel rates. Sometimes hotels offer the best rate directly, especially if you’re staying 3 or 4 nights. We also used Hotwire to book hotels. Hotwire offers cheaper rates by NOT telling you what hotel you’re booking. When using Hot Rate you pick an area and it gives you some clues which hotel it might be. It was fun trying to figure out which hotel we’d get. We ended up saving loads of money this way.
• Pack clothes for all conditions. The weather in San Diego was sunny and low 70s, San Francisco was foggy, at times windy, and cold. The temperature was high 50s – mid 60s. While Calistoga in Wine Country was HOT – 99 degrees while we were there. We packed jeans, long sleeved shirts, waterproof coats, as well as, summer clothing. I would also recommend mixing the clothes across the bags just in case luggage gets lost or stolen. We did have an incident at the very end of our trip (where my suitcase and Luke’s backpack was stolen from the car).
• Don’t leave valuables in the car. This is true in the bigger cities certainly. Although, we did leave our bags in places that were more rural.
• Stock up on snacks and water. There are loads of Trader Joe’s in California so we’d stock up on bottled water, RX and Cliff Bars, Nuts and fresh fruit. Most days we’d eat breakfast, have bars or fruit for lunch and then eat dinner out. I think that’s the hardest part about a road trip, no home cooking. I certainly missed making us meals while we were away (wow, never thought I’d say that!!!).
• It’s okay to be a tourist. We booked some tours – wine tours and a Hollywood Tour. It was easier to see the city with an expert tour guide. I also recommend buying a travel guide. I bought this guide (affiliate link) and loved it as an overview. I read some before we went and also read while we were driving to give the boys an idea of things to do or what areas were famous for. Also, the hotels have lots of great local information in the rooms. Some hotels offer concierge services and may be able to get you cheaper tickets or earlier entry at some attractions.
• Don’t overbook yourself. We booked the hotels and things that were recommended to be booked ahead, like Universal Studios and Hearst Castle. Alcatraz books up 90 days ahead so we were unable to go to the prison. We tried to leave our days pretty open so we could decide on the day what we wanted to do. If you overbook yourself, you risk becoming a slave to a schedule you set weeks ahead. We stumbled on really unique places which was so fun.

I hope that answered a few travel questions! In the coming weeks I’ll be sharing individual posts on each of the areas we visited, I’ll include accommodations, things we loved about the area, and other tips. Do you have any specific questions or anything you’d like to know. Please leave a comment or email me. I’d love to help you plan your next family road trip to California.