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Road Trip Itinerary for 2 Weeks in California

Road Trip Itinerary 2 Weeks California

Updated: September 2023

It’s time to fall in love with the Golden State. Maybe I am partial, but I think my home state is one of the most incredible places in the world. With endless natural beauty and a one-of-a-kind culture, California has something for everyone.

Just follow your heart along the Pacific Coast Highway!

Ready for the ultimate road trip? Check out my road trip itinerary for 2 weeks in California.

If you don’t have two weeks, be sure to check out my 3-Day California Coast Road Trip or the 10-Day California Coast Road Trip Itinerary!

California Coast Road Trip Beach

California Itinerary Overview

California can be traveled by train, plane, and automobile—but I personally think the best way is by road trip! You can start your California road trip in either direction and spend as little or as much time in a destination as you like. This would be a pretty rushed itinerary, but it hits all of my favorite highlights along the California coast!

  • Days 1-2: San Diego

  • Day 3: Joshua Tree

  • Day 4: Palm Springs

  • Day 5: Orange County

  • Day 6-7: Los Angeles

  • Day 8: Santa Barbara

  • Day 9: Big Sur

  • Day 10: Monterey

  • Day 11-12: San Francisco

  • Day 13-14: Winelands

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Renting an RV?

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Whether planning a cross-country expedition, a weekend escape to nature’s embrace, or just itching to chase the sunset on a whim, look no further than RVshare. Embrace the open road, make memories that’ll last a lifetime, and let the journey be as incredible as the destination.

Visit RVshare to find the perfect RV rental in California!

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Days One & Two: San Diego

Fly into San Diego International Airport

With beautiful beaches, 100+ days of sunshine a year, a world-famous zoo, and an incredible craft beer scene, San Diego is the perfect city to start your Californian adventure.

Give it at least two days, and it’ll knock your flip-flops off!

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Day Three: Joshua Tree

Drive 2 hours and 45 minutes from San Diego to Joshua Tree

Nestled among a range of eclectic towns and overlooking the Coachella Valley, Joshua Tree National Park has a rugged desert beauty that is unforgettable.

Bring your camera and a good pair of shoes, and devote at least one day to exploring.

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Palm Springs Girl Road Trip

Day Four: Palm Springs

Drive 50 minutes from Joshua Tree to Palm Springs

A dream destination for a girlfriends’ getaway or a spa escape, Palm Springs is one desert resort city that is always at the top of my must-visit list anytime I am stateside.

Check out some of my favorite hangouts, like Riviera Palm Springs and ARRIVE.

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Day Five: Orange County

Drive an hour and a half from Palm Springs to Orange County

With world-class galleries, coves, and beaches, Laguna Beach is one of the sparkling jewels of Orange County. Two other essential coastal cities, Newport and Huntington Beach are great for long summer days. Walk the piers, lounge at the beach, and then head over to try one of their great restaurants.

A visit to Orange County is not complete without a visit to the Happiest Place on Earth! I grew up going to Disneyland and it will always hold a special place in my heart. It’s a great place to spend the day with friends and family for endless fun.

Santa Monica Pacific Coast Highway

Day Six & Seven: Los Angeles

Drive 1 hour from Orange County to Los Angeles

Los Angeles is one of the world’s great cities, and you’ll want at least two days to see the different sides. Of course, first-time visitors have to check out quintessential spots like Malibu, Beverly Hills, Hollywood, and Venice Beach.

Once you’ve seen the city, head to the stunning sunny coastline. Explore El Matador State Beach, El Porto Beach (a surfer hot spot), and Abalone Cove Ecological Reserve.

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Day Eight: Santa Barbara

Drive 2 hours from Los Angeles to Santa Barbara—for the scenic route take Pacific Coast Highway (Hwy 1) all the way up the coast!

A top pick on the American Riviera, Santa Barbara has great stops for foodies, awesome shopping, and sun-drenched beaches. What more could you ask for?

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Bixby Bridge in Big Sur

Day Nine: Big Sur

Drive 5 hours from Santa Barbara to Big Sur

For a primo glamping experience, this is where you want to be. Pullover, grab a tent, and forget about the world in one of the most picturesque locations in the US. You’ll find gems all the way up and down Hwy 1.

While you’re in Big Sur, be sure to check out the Esalen Institute. A blend of Western tech and Eastern science, you’ll find workshops ranging from yoga to healing arts.

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Day Ten: Monterey

Drive one hour from Big Sur to Monterey

Explore the rugged coastline, and then go over to Cannery Row to wander through the turn-of-the-century canneries while you explore the modern shops and seafood restaurants.

And don’t miss the Monterey Aquarium for some selfies with jellyfish! Ranked among the world’s best aquariums on the planet, this place is magical and educational.

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Days Eleven &  Twelve: San Francisco

Drive 2 hours from Monterey to San Francisco

Honestly, you could spend two weeks exploring the iconic sights of San Francisco. With endless Michelin-starred restaurants, fascinating spots like Alcatraz Island, the picture-perfect Golden Gate Bridge, and trendy ‘hoods, like The Mission and The Marina, San Francisco is one of California’s greatest cities.

Be sure to get around to my favorite places, Pier 39 on Fisherman’s Wharf and Chinatown.

Read More:

California makes some of the best vino in the world!

Days Thirteen & Fourteen: California Winelands

Explore the vineyards of Napa Valley and Sonoma County, and taste your way through this foodie paradise.

You can go on a DIY tour, hop on the Napa Wine Train, or check out the Wine Country Shuttle Tour. For a breathtaking view, you have to see the sights from one of the amazing hot-air balloon tours.

Read More:

The Coolest Airbnbs in California

Here are the coolest (and most charming) Airbnbs to stay at in California!

Read More

Plan Your Trip

Want to use this itinerary for your road trip but add a few of your own twists to it? I love using Roadtrippers to plan out my stops—figure out how long I’m driving in between them, and find popular spots and pit-stops along the way.

Looking for other California goodies? Check out these!

Have you visited California before? What places did you explore? Let me know in the comments below!

Shop My Favorite California Coast Styles!

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    1. Umina Beach

      Wine land is one of my favorite I hope I can visit soon!

      January 15, 2018 at 7:59 pm · Reply
    2. Umina Beach

      Wine land is one of my favorites I hope I can visit soon! cheers

      January 15, 2018 at 8:00 pm · Reply

    Instagram

    Dia de Los Muertos in Oaxaca 🇲🇽💀🪅
    •••••••••••••••••••••••••••••••••••••••••
    I’ve wanted to visit Oaxaca for as long as I can remember, and it was so special getting to be there for the days leading up to Dia de Los Muertos (celebrating my boo @kpande)!

    Dia de Los Muertos is celebrated in different parts of Mexico, to pay respects and remember friends and family members who have passed on.

    The festivities are colorful, joyful, and often humorous. Coming from a culture where the deceased are so quickly forgotten, I think this tradition is so beautiful.

    Oaxaca is such a vibrant city with endless street art and incredible food. I can’t wait to return!
    •••••••••••••••••••••••••••••••••••••••••
    #oaxaca #mexico #diadelosmuertos #diademuertos

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    Dia de Los Muertos in Oaxaca 🇲🇽💀🪅 ••••••••••••••••••••••••••••••••••••••••• I’ve wanted to visit Oaxaca for as long as I can remember, and it was so special getting to be there for the days leading up to Dia de Los Muertos (celebrating my boo @kpande)! Dia de Los Muertos is celebrated in different parts of Mexico, to pay respects and remember friends and family members who have passed on. The festivities are colorful, joyful, and often humorous. Coming from a culture where the deceased are so quickly forgotten, I think this tradition is so beautiful. Oaxaca is such a vibrant city with endless street art and incredible food. I can’t wait to return! ••••••••••••••••••••••••••••••••••••••••• #oaxaca #mexico #diadelosmuertos #diademuertos

    If you’re finding yourself here for the first time, welcome! I’m sharing my New England Road Trip (with a Toddler) series, and it’s Day 3 of our adventure! 🍂🍁
    ••••••••••••••••••••••••••••••••••••••••••••••
    I’m sharing some insider info on hiking the legendary Flume Gorge in New Hampshire.

    We opted to stay in North Conway, NH and used it as a base to explore the White Mountains. We stayed at Kearsarge Inn and @oldvillagebakerynh was literally next door.

    We grabbed some pastries and bagels for the road and drove about an hour to Flume Gorge– a 2.2-mile self-guided hike with covered bridges, amazing waterfalls, and gorgeous mountain views.

    TIP: You need to book tickets with a dedicated time slot for entry to hike Flume Gorge. I did this about 2 months in advance given how busy the foliage season is here. So BOOK EARLY and ARRIVE EARLY.

    Most people can do the hike in about 1.5 hrs, but I’d add an hour with young kids. We did lots of nature exploring and resting along the way.

TIP FOR YOUNG KIDDOS: Bring a baby carrier or hiking backpack! While this is rated a family-friendly hike, it wasn’t without some challenges with a toddler. I ended up carrying him on my shoulders for over a mile which was an adventure in itself.

    I had bookmarked Artist’s Bluff Lookout and Polly’s Pancake Parlor to do after, but like with all plans with kids, they change as need. We opted to call it a day after the first hike but you can definitely add Artist’s Bluff to your day (it’s just a few minutes up the highway).

We did drive to Polly’s because pancakes sounded amazing, but the wait was 2.5 HOURS at 11am. So we passed.

We had a relaxed afternoon back in North Conway and went to @conwayscenicrailroad to watch the trains come into the depot. You can book a scenic ride too!

    If you’re planning a similar road trip, you’re not gonna wanna miss Day 4 for arguably the MOST famous scenic byway in all of New England during the foliage season!
    ••••••••••••••••••••••••••••••••••••••••••••••
    @visitnh #fallroadtrip #fallfoliage #portlandmaine #newengland #autumn #visitnh #visitnewhampshire

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    If you’re finding yourself here for the first time, welcome! I’m sharing my New England Road Trip (with a Toddler) series, and it’s Day 3 of our adventure! 🍂🍁 •••••••••••••••••••••••••••••••••••••••••••••• I’m sharing some insider info on hiking the legendary Flume Gorge in New Hampshire. We opted to stay in North Conway, NH and used it as a base to explore the White Mountains. We stayed at Kearsarge Inn and @oldvillagebakerynh was literally next door. We grabbed some pastries and bagels for the road and drove about an hour to Flume Gorge– a 2.2-mile self-guided hike with covered bridges, amazing waterfalls, and gorgeous mountain views. TIP: You need to book tickets with a dedicated time slot for entry to hike Flume Gorge. I did this about 2 months in advance given how busy the foliage season is here. So BOOK EARLY and ARRIVE EARLY. Most people can do the hike in about 1.5 hrs, but I’d add an hour with young kids. We did lots of nature exploring and resting along the way.

TIP FOR YOUNG KIDDOS: Bring a baby carrier or hiking backpack! While this is rated a family-friendly hike, it wasn’t without some challenges with a toddler. I ended up carrying him on my shoulders for over a mile which was an adventure in itself. I had bookmarked Artist’s Bluff Lookout and Polly’s Pancake Parlor to do after, but like with all plans with kids, they change as need. We opted to call it a day after the first hike but you can definitely add Artist’s Bluff to your day (it’s just a few minutes up the highway).

We did drive to Polly’s because pancakes sounded amazing, but the wait was 2.5 HOURS at 11am. So we passed.

We had a relaxed afternoon back in North Conway and went to @conwayscenicrailroad to watch the trains come into the depot. You can book a scenic ride too! If you’re planning a similar road trip, you’re not gonna wanna miss Day 4 for arguably the MOST famous scenic byway in all of New England during the foliage season! •••••••••••••••••••••••••••••••••••••••••••••• @visitnh #fallroadtrip #fallfoliage #portlandmaine #newengland #autumn #visitnh #visitnewhampshire

    The Ultimate Fall Foliage Itinerary for New England (toddler edition)! 🍁
    ••••••••••••••••••••••••••••••••••••
    We flew in and out of Boston — and you’ll need to rent a car. This trip involves a lot of driving!

    @Expedia is my go-to resource for travel— you can rent your car, book activities, and find amazing accommodation for your own trip to New England!

    You can start your adventure in North Conway, in the white mountains of New Hampshire. This cute town is home to the Conway Scenic railway and is a great base to explore some of the best leaf peeping in the area.

    You’ll want to book tickets for Flume Gorge months in advance—it’s a kid-friendly hike but still 2.2 miles and I definitely regretted not bringing a hiking carrier for Ollie.

    Head out EARLY to drive the 34-mile Kancamagus Scenic Byway—there are tons of spots to stop along the byway, but we loved Sabbaday Falls for a short hike with big reward.

    Next up, head to Woodstock, Vermont, and check into Woodstock Inn. This hotel sells out almost a full year in advance during foliage season, so plan ahead.

    Don’t miss a maple creamy from Woodstock Scoops or a visit to Billings Farm.

    The entire drive through Vermont is SO beautiful. On your way to the town of Stowe, stop for some apple picking, and don’t miss Hollow Cider for cider donuts.

    Stay at the Trapp family lodge (owned by the REAL family from the Sound of Music). This is such a great spot for kids. They have tons of farm animals like highland cattle and sheep. Stowe is famously known for its crowds this time of year, so if you want to avoid them, base yourself here, take in the incredible views, and go on hikes directly on the property.

    Stay at the Trapp family lodge (owned by the REAL family from the Sound of Music). They have tons of farm animals like highland cattle and sheep. There’s a beer hall, bakery, and even hiking trails on the property—so you can avoid the crowds in town. It’s also located near the Smuggler’s Notch mountain pass.

    End your trip by driving back to Boston and spending a couple of days exploring one of the most historic (and kid-friendly) cities in America!
    ••••••••••••••••••••••••••••••••••••
    #newengland #autumn

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    The Ultimate Fall Foliage Itinerary for New England (toddler edition)! 🍁 •••••••••••••••••••••••••••••••••••• We flew in and out of Boston — and you’ll need to rent a car. This trip involves a lot of driving! @Expedia is my go-to resource for travel— you can rent your car, book activities, and find amazing accommodation for your own trip to New England! You can start your adventure in North Conway, in the white mountains of New Hampshire. This cute town is home to the Conway Scenic railway and is a great base to explore some of the best leaf peeping in the area. You’ll want to book tickets for Flume Gorge months in advance—it’s a kid-friendly hike but still 2.2 miles and I definitely regretted not bringing a hiking carrier for Ollie. Head out EARLY to drive the 34-mile Kancamagus Scenic Byway—there are tons of spots to stop along the byway, but we loved Sabbaday Falls for a short hike with big reward. Next up, head to Woodstock, Vermont, and check into Woodstock Inn. This hotel sells out almost a full year in advance during foliage season, so plan ahead. Don’t miss a maple creamy from Woodstock Scoops or a visit to Billings Farm. The entire drive through Vermont is SO beautiful. On your way to the town of Stowe, stop for some apple picking, and don’t miss Hollow Cider for cider donuts. Stay at the Trapp family lodge (owned by the REAL family from the Sound of Music). This is such a great spot for kids. They have tons of farm animals like highland cattle and sheep. Stowe is famously known for its crowds this time of year, so if you want to avoid them, base yourself here, take in the incredible views, and go on hikes directly on the property. Stay at the Trapp family lodge (owned by the REAL family from the Sound of Music). They have tons of farm animals like highland cattle and sheep. There’s a beer hall, bakery, and even hiking trails on the property—so you can avoid the crowds in town. It’s also located near the Smuggler’s Notch mountain pass. End your trip by driving back to Boston and spending a couple of days exploring one of the most historic (and kid-friendly) cities in America! •••••••••••••••••••••••••••••••••••• #newengland #autumn

    Welcome back to Day 2 of my Autumn New England Road Trip (with a toddler)! 🍂
    •••••••••••••••••••••••••••••••••••••••••••
    I’m sharing one of the coolest activities not only in Portland, Maine, but on our entire trip: @childrensmuseum_theatreofmaine

    But first, we started our day with the best bagels I’ve ever had at @_rose_foods_ — OMG they were so good.

    Then it was off to the Children’s Museum. It happened to be a super rainy day, so it was the perfect indoor activity.

    What you can expect: the museum is an interactive kids’ museum with the coolest water table exhibit and lots of science & job-related play exhibits. Be sure to buy your tickets in advance—it’s a really popular spot for families!

    After that, we stopped by @allagashbrewing for some lunch. Allagash White has been one of my favorite beers for years—and it was amazing to see the brewery in person. (TIP: During the Fall, you can ask for a sugary, pumpkin rim. It’s SO good!) They also have some kid-friendly activities and tasty food.

    We made our way to New Hampshire and checked into the Kearsarge Inn in North Conway—it’s the cutest tiny town that’s home to the Conway Scenic Railway.

    We based ourselves here to explore the most beautiful drives and hikes in the White Mountains during autumn.

    Stay tuned for Day 3 & 4 for some of the most incredible hikes and scenic byways!
    •••••••••••••••••••••••••••••••••••••••••••
    @visitportland @visitmaine
    #fallroadtrip #fallfoliage #portlandmaine #newengland #autumn #visitportland #visitmaine

    1040 23
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    Welcome back to Day 2 of my Autumn New England Road Trip (with a toddler)! 🍂 ••••••••••••••••••••••••••••••••••••••••••• I’m sharing one of the coolest activities not only in Portland, Maine, but on our entire trip: @childrensmuseum_theatreofmaine But first, we started our day with the best bagels I’ve ever had at @_rose_foods_ — OMG they were so good. Then it was off to the Children’s Museum. It happened to be a super rainy day, so it was the perfect indoor activity. What you can expect: the museum is an interactive kids’ museum with the coolest water table exhibit and lots of science & job-related play exhibits. Be sure to buy your tickets in advance—it’s a really popular spot for families! After that, we stopped by @allagashbrewing for some lunch. Allagash White has been one of my favorite beers for years—and it was amazing to see the brewery in person. (TIP: During the Fall, you can ask for a sugary, pumpkin rim. It’s SO good!) They also have some kid-friendly activities and tasty food. We made our way to New Hampshire and checked into the Kearsarge Inn in North Conway—it’s the cutest tiny town that’s home to the Conway Scenic Railway. We based ourselves here to explore the most beautiful drives and hikes in the White Mountains during autumn. Stay tuned for Day 3 & 4 for some of the most incredible hikes and scenic byways! ••••••••••••••••••••••••••••••••••••••••••• @visitportland @visitmaine #fallroadtrip #fallfoliage #portlandmaine #newengland #autumn #visitportland #visitmaine
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