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May 2023 Inspiring Itinerary: The Perfect California Road Trip

Highway 1 California

Why a Road Trip?

In one of our latest blogs, “Top Ten Journeys of a Lifetime,” an “Epic Road Trip” was one of the featured Journeys. Why? Because there’s just something about the open road, right? The spark of adventure, the endless possibilities, the inherent belief that it’s about the journey as much as the destination. Plus, of course, the inevitable connections and revelations that occur between the people traveling together. An Epic Road Trip almost feels like a rite of passage no matter when you take one, because it doesn’t have to be a rite of passage into something like adulthood, but instead it’s a rite of passage into a new version of yourself. 

Big Sur Highway 1

One of the best parts about a road trip is that the open road in front of you can lead you anywhere, up or down a Coastline, from one Coast to another, and anything in between. Personally, I’m partial to a Road Trip along the Coast, because nothing beats a scenic ocean drive, and for May’s Inspiring Itinerary, that’s exactly what we’re featuring: The Perfect California Road Trip!

California Road Sign

Why California?

The “Golden State” has been drawing people from all over the country, and the world, for almost 200 years, starting with the “Gold Rush” back in the mid-1800s. Nowadays though, the “Gold” that people “Rush” to see is more in the form of the Golden Gate Bridge, those Gold Stars along Hollywood Boulevard, and the picturesque Golden beach sunsets that California is so famous for. And it’s not just “all that glitters” that makes people want to visit California; the things to do and sights to see are seemingly endless, and are also incredibly diverse, so there’s truly something for everyone to love in the Golden State. 

Santa Barbara

With so much to do, one of the best ways to explore the state, and cover the most ground, is by Road Tripping! And even by narrowing our travel options down to a Road Trip, there are still a plethora of options in California, depending on your preferences. There are tons of State and National Parks to visit, Wine Country to taste your way through (with a Designated Driver, of course), and with 840 miles of coastline, a drive with an Ocean view is not hard to come by. In fact, one of the most famous Road Trips to take throughout the whole world is along the Pacific Coast Highway, which is exactly where this month’s Inspiring Itinerary takes us! Buckle up and get ready for the drive of a lifetime!

Let’s Go!

Fisherman's Wharf

Day 1 

The first step to the Perfect Road Trip is…picking the perfect car, of course! Depending on your preferences and who you’re traveling with, that might be a convertible, or a Jeep that can off-road, or a Luxury SUV. Whatever your choice, your favorite Love of the Magic Travel Advisor can help make sure your Road Trip starts out right! And you’ll pick up your preferred car right after you arrive in San Francisco, where your epic adventure will begin! Whatever time your flight gets in, you’ll have the rest of the day or evening to explore the area around Fisherman’s Wharf, where you’ll be staying in a boutique, luxury hotel overlooking the Bay. 

Golden Gate Bridge

Day 2 

Another key component to experiencing a Perfect Road trip is to make the most of your time at each stop, so that you’re not packing up to stay somewhere new every single night (unless you really love that cover-more-ground, pack-up-and-go everyday style, which is great for super long Road Trips). Today, after breakfast at a local bakery with a side of salty bay breeze, you’ll head out to see some of San Francisco’s most iconic landmarks: The Painted Lady Houses, Lombard Street, a ride on Cable Car, and, obviously, The Golden Gate Bridge. 


Stop at Golden Gate National Recreation Area before crossing over the famous Bridge to spend the afternoon in Sausalito, the American equivalent of Italy’s Amalfi Coast. Stroll along the Downtown Waterfront area, popping in and out of souvenir and ice cream shoppes, and then grab an early dinner at one of the fish restaurants on the water. Afterwards, if the San Francisco Giants are in town, you might catch a baseball game before heading back to your hotel, or you could even take a boat over to Alcatraz for a nighttime ghost tour, if you dare. Both would need advance reservations, which your LOTMV Travel Advisor can help with, as always!


Day 3 

Once again this morning, after checking out of your first hotel, you’ll head out back over the Golden Gate Bridge for a last stretch of driving North as you make your way to Tiburon, another seaside town just across the water from Sausalito, but much smaller and a bit more quaint. Here you can grab a leisurely breakfast by the water, and wander through some boutiques and galleries before setting out towards the real activity of the day: exploring Muir Woods.

Muir Woods

Part of the National Park Service since 1908, Muir Woods National Monument is home to old growth coast redwoods that reach towering heights. Take your time exploring this National Park before setting out for your first longer stretch of driving along historic Highway 1. You’ll cross the Golden Gate one last time as you continue South, landing in Monterey for the night. 


Day 4 

Today is all about the beachy towns of Monterey and Carmel-by-the-Sea. Start your day with some great family-oriented activities, such as the Monterey Bay Aquarium, the Monarch Butterfly Sanctuary, and exploring the Old Fisherman’s Wharf and Cannery Row, a stretch of shops (that used to be part of the sardine-packing industry) made famous by John Steinbeck. Then head over to Carmel-by-the-Sea, a quaint, Provincial-like town filled with specialty boutiques, galleries, and bistros that feature wine tastings and local flavors. Though Carmel is somewhat more adult-centric than Monterey, hopefully the kiddos will be tired out from the morning adventures, and be able to relax either in strollers, or even on sidewalk benches with a bit of screen time, while Mom gets to indulge in some shopping time. 

Carmel by the Sea

You can also pop down to the beach if the kiddos start to get restless, which is worth doing anyway, because it’s a beautiful California Coast Beach, of course! Both Monterey and Carmel are bursting with incredible restaurant options, so the only tough thing about dinner will be deciding where to go! Then you’ll head back to your hotel in Monterey for one more night before setting off to the next stop in the morning!

Bixby Creek Bridge

Day 5 

Get ready for the Holy Grail of Road Trips. Today is all about the road, the views, and the discoveries and treasures you find by stopping along the way, so be ready to set out early to make the most of the day! You’ll set out from Monterey on Highway 1, hugging the rugged coastline for a bit until you come to the famous Bixby Creek Bridge, one of the most photographed bridges in California (impressive, with the Golden Gate to compete with), where there are places to pull over to get pictures of your own. 

McWay Falls

Then, after crossing the bridge, continue along Highway 1 through Big Sur to your lunch destination, a restaurant called Nepenthe, where you can sit as close to the cliff edge as possible, and feel like you’re dining on the edge of the Earth. Don’t miss the eclectic gift shop, The Phoenix Shop, while you’re there! After lunch, keep going South on Highway 1 to the Waterfall Trail in Julia Pfeiffer Burns State Park, where you can hike a very short distance to see McWay Falls from above, along with some incredible coastline views. 

Highway 1

With a great meal and a hike to stretch your legs under your belt, it’s time for a longer bit of driving as you continue South on Highway 1, before heading inland slightly to reach Hearst Castle. While you probably won’t have time to cover the entirety of the huge mansion and property, there are smaller tours available, and it’s worth seeing the Castle just to see the incredible design and artwork, and to see how the incredibly rich lived in the early 1900s. 

California Castle

Once you’re finished exploring Hearst Castle, you’ll make your way back to Highway 1, and drive South until you reach Pismo Beach. Depending on the timing, you might be hitting this beautiful beach right at golden hour, which can afford you, not just an extra-gorgeous experience, but some truly fabulous photos, too. This stop might also be a good opportunity to grab a bite for dinner at one of the seafood restaurants along the beach before the final stretch of your drive for the day, which will bring you into Santa Barbara for the night. 

Solvang California

Day 6 

Although the beautiful town of Santa Barbara will be beckoning this morning, head out before breakfast for a quick drive to the town of Solvang, a Danish enclave complete with Windmills, and you guessed it, Danish pastries (now you know why I said don’t eat breakfast before leaving!). After a little stroll around “Denmark in America,” continue your European-inspired day by driving back to the Spanish-influenced Santa Barbara. 

Santa Barbara

Here you can tour the Old Mission church, hike one (or more) of the numerous trails in the area, with some trails even leading to waterfalls, visit the old rusty pier and stage an impromptu photo shoot, explore the Maritime Museum, or just wander around the beaches or shops or both that abound around town. For dinner, you can ask a local or your hotel staff for a recommendation to one of the excellent restaurants Santa Barbara has to offer. 

Malibu State Park

Day 7 

Today you’ll set off on your drive once more, for the last long stretch along Highway 1. As you make your way through Malibu, you’ll surely notice the effects of the devastating fire from a few years ago, but you’ll also see how much rebuilding has been done, and sense how resilient the human spirit can be. Make a stop at Malibu Pier for lunch with a view and a stroll along the beach. Continue on your way to another pier, the famous Santa Monica Pier, where you can ride the iconic Ferris Wheel, and take a spin on a few other amusement rides, too. 

Santa Monica Pier

Walk along the beach, or into downtown for some high end shopping, and don’t forget to grab some snacks along the way to hold you over on your last bit of driving. Maybe even get a stash of snacks for the car, too, since the drive from here to your final destination is notoriously trafficky. But don’t worry, your last stop is Disneyland, so the tough drive will be worth it as soon as you check in to your Disney Resort for the night!


Day 8

What better way to end your Perfect California Road Trip than at the Happiest Place on Earth, Disneyland? Here you can relax into the familiarity of Disney, while still having a fun-filled and exciting finale to your vacation. One of the best parts of Disneyland is how close the two parks, Disneyland Park and California Adventure Park, are to each other; with a Park Hopper ticket, you can go back and forth between them as much as you please. 

Cozy Cone Motel Disneyland

Spend your first day at the Parks hitting up all of your favorite rides, such as Big Thunder Mountain Railroad, Radiator Springs Racers, Incredicoaster, and whatever other attractions you love, to make sure you check off all of your “Must-Do”s so you don’t have to worry about getting to anything on your very last day. Don’t forget to watch for wandering characters, since Disneyland is full of characters who love to walk around and interact with guests! For dinner, you can eat in one of the Parks or at your Resort (though if you have something specific in mind, make sure to let your favorite Love of the Magic Vacations Travel Advisor know, so that she can remind you when your dining window opens).

Disneyland Castle

Day 9

Make the most of your last day in Disneyland, and also your last day of your Perfect California Road Trip by starting out with a quintessential Character Breakfast at one of the restaurants in the Parks or Resorts (once again, make sure your LOTMV Travel Advisor knows you want to do this and helps you snag reservations if you need). Then spend the day making your way around the Parks, and getting to everything you didn’t have time for yesterday. You might even want to ride one of your favorites one last time, or just mosey down Main Street U.S.A. people watching, or wander through the park trying all the treats, and doing some well-deserved Disney shopping. Make sure you have a great reservation for dinner on your last night, too, and definitely stay for the fireworks!

Pacific Coast Highway

Day 10 

Remember way back on Day 1, when the first step of your Perfect Road Trip was picking your perfect car to journey with? Today, you’ll thank your amazing car companion, and bid her farewell as you drop her off at the L.A. Airport to catch your flight home. The last day of vacation is always sad, but especially so when you may have grown attached to an integral part of your journey! But never fear! If you loved Road Tripping, and literally being in the driver’s seat of your adventure, there are endless opportunities for more Road Trips all over the country, and even all over the world, too! And while one of the best parts of a Road Trip is the open road when you start out, another amazing aspect of Road Trips is looking back at the journey you’ve taken, how far you’ve come, and all you’ve experienced along the way!

Pacific Coast Highway

Ready to Plan?

If you are ready to plan The Perfect California Road Trip Vacation, contact your Love of the Magic Travel Agent today, or email  And of course, whether you want to Road Trip down the California Coast, or up the East Coast, or Cross Country, or anywhere else, your LOTMV Travel Advisor will work with you to create the unique experience you’re looking for. 

Looking for more of our Inspiring Itinerary series?

You can find links to all of 2022’s Inspiring Itineraries in this Blog: A Year of Inspired Travel: 2022’s Inspiring Itineraries, Month by Month

Just like last year, a new Inspiring Itinerary will come out each month!

So far, we have:

January 2023: The Perfect Themed Vacation, by Land and by Sea

February 2023: The Perfect Romantic Escape to Jamaica

March 2023: The Perfect Foodie-Inspired Vacation to Portugal

April 2023: The Perfect Parisian Vacation: Paris and Disneyland Paris

And don’t forget to check out our Friday Blog Series: Jamie’s Destination “Do”s and “Don’t”s, where our favorite Travel Planning Aficionado shares her wealth of knowledge and experiences about traveling the world! You can find links to all of Jamie’s 2022 Travel Tips at this Blog: Jamie’s 2022 Destination “Do”s and “Don’t”s: A Recap

Ready to plan The Perfect California Road Trip? Contact your Love of the Magic Vacations Travel Advisor today or email 

California Road Trip Inspiring Itinerary



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