Southern California Road Trip: San Diego to San Francisco

September 6, 2018   /   bynatalie  / Categories :  Travel
Hollywood sign California

There’s no better way to travel. Road tripping gives you the opportunity to explore a destination at your own pace, stopping when you see something interesting or driving like the wind when your next stop is super exciting. You can get a real feel for a place from watching the landscape and the sky change. And there’s no better place to road trip than the west coast of the USA. I hit the road with my friends Kiersten and Meyer for an epic drive that had us winding along the California coast from San Diego all the way up to San Francisco.  Here’s my guide to Southern California road tripping.

Santa Barbara beach

Could my tour guide be more of a babe?

Planning your Southern California road trip

When it comes to road tripping in California, you’re going to need a car. And even if you’re a real freewheeling traveller, you’ll also need a bit of a plan so that you don’t miss out on the major highlights and local gems. I was lucky enough to have my own California native tour guide in The Blonde Abroad, and she planned all our stops along the way. In terms of distance, you could do the drive in a day if you needed to, but we spent over a week exploring the route. Spending a few nights in San Diego before heading to Los Angeles, then on to Santa Barbara, San Luis Obispo, Big Sur and finally San Francisco gave enough time to really see the route. Of course no great American road trip is complete without a great variety of American snacks, including Swedish Fish, Twizzlers, Sour Patch Kids, David’s Sunflower Seeds (kinda gross but addictive), Flamin’ Hot Cheetos and Chex Mix.

road trip Taco stand San Diego USA

I’ll take one of everything!

Southern California Road Tripping

from San Diego to San Francisco

Start in: San Diego

Little Italy San Diego street art

Walking the streets of Little Italy with my little Californian

What to expect in San Diego : I honestly had no idea San Diego would be so cool. Known as California’s most liveable city (not to South Africans, I’ll tell ya that), it’s got clean, wide open streets, wide open skies, beautiful beaches and a really laid-back California culture. One of the best things about San Diego was the Mexican food, which is on pretty much every menu!

Where to stay: We rented a really cute bungalow in Little Italy on Airbnb. The streets are flat and the climate is a dream, so walking is easy. There’s also lots of street art, a cool coffee shop scene and loads of colourful street art. Like most of the other stops along the way, parking can be a nightmare, so plan to walk as much as possible or take Ubers when you need to go a little further.

What to do in San Diego

Bilboa Gardens San Diego California USA

Grab a burger at In-n-Out: You can’t go to California without stopping at In-n-Out. Literally the best fast food burgers in the world. Don’t forget to order it “animal style with chopped chillies” (IMPORTANT!).

See a classic movie at the Rooftop Cinema: The Rooftop Cinema Club screens classics on top of the Manchester Grand Hyatt Hotel, which has possibly the best views in the city. Comfy chairs, blankets, snacks and a bar await. We saw Jaws up there and it was the best!

Explore Little Italy: Coffee shops, boutiques and cool restaurants are dotted between awesome street art.

Visit Bilboa Gardens: Even bigger than Central Park, Bilboa Park is a really pretty place to spend the morning walking around and taking about a thousand photos.

Watch a game at a sports bar: Complete with buffalo wings and ranch dip, a huge variety of local craft beers and the game on TV. We visited Bub’s At The Ball Park on a mid-week afternoon while there was a baseball game on at the stadium next door and the vibe was awesome! I felt like I was in some kind of American sitcom.

Chill out at Coronado Beach: We took a drive out to sprawling white sand beach across the bay to the Hotel del Coronado, which looks like a Wes Anderson movie set and is famous for hosting Hollywood stars like Marilyn Monroe.

Cocktails in La Jolla: Ocean views with a side of margaritas, anyone?

Mission Beach & Pacific Beach: Grab an electric scooter and cruise along the beachfront, like an extra in particularly fully-dressed episode of Baywatch. This looong stretch of beach is exactly like what I imagined the coastal locations where American kids spend their spring breaks and summer vacations would be like.

San Diego to Los Angeles | 2,5 hours

Venice beach California sunset

What to expect in Los Angeles: Literally just celebrities everywhere. Kidding. LA is a sprawling city with lots of iconic neighbourhoods that each have their own distinct culture. It really felt pretty surreal being there for the first time, walking the streets that we grew up seeing on our TV and movie screens.

Where to stay: We stayed in a really gross Airbnb (not linking it for that reason), but in a really great part of town. West Hollywood is the ideal place to base yourself for getting around. Having said that, make 100% sure you book somewhere with parking, and then don’t even think about getting your car out again because there’s no parking anywhere and valet parking looks cool but costs like $15 a pop and its much more convenient to just Uber everywhere.

What to do in Los Angeles

santa Monica pier Los Angeles california usa

Walk the Santa Monica Pier: The iconic pier that marks the end Route 66 is bustling with people, street performers and tourists. Go hungry because there are A LOT of snacks to choose from.

See Venice Beach at sunset: That Venice street sign is iconic, and seeing it at sunset makes for a memorable picture. Venice also has some excellent shopping, so hit up Abbot Kinney Boulevard.

Take a picture at the Hollywood sign: We drove up towards the Hollywoodland nieghbourhood to see the sign from afar, since we didn’t have the time or inclination to hike up to it. I actually think I loved seeing it this way more!

Shop at The Grove: You’ve definitely heard The Grove mentioned in movies and on TV. I remember the characters in the defining shows of my teenage years talking about it. It feels like a theme park and it’s a great place to shop. There’s a big food market that’s worth a visit too.

Have a fancy dinner at Catch: I was obviously very lucky to be in town with an LA native, which is the only reason I went here. But I highly recommend it because it’s so LA it hurts. Which is what you want when you’re in LA, obviously. Be sure to reserve a table and then keep your eyes open because a quick Google image search for celebrities at Catch LA is all the convincing you need to know that this is a serious hotspot.

Party till late at Doheny Room: I’m not a big nightclub person but I’m not going to turn down an invitation to one of the hottest clubs in LA, complete with a private table and bottle service. I mean who do I think I am? The music was actually so good and although the drinks were eyewateringly expensive when we went up to the bar we had a great time until after 2am. Followed of course by 3am tacos.

See a movie in Hollywood: I was very surprised to see how sad the movie theatres in the US are compared to South Africa, but seeing a Hollywood movie in Hollywood just felt like something I absolutely had to do. I bought a ticket for Charlize Theron’s Tully (extra points for seeing a Hollywood movie starring a South African actress in Hollywood) all by myself on a hungover day and it was a 10/10 experience.

Get your hair blown out (as the Americans say) at a The Drybar: Because trying to wash and style your hair in a grimy Airbnb or tiny hotel room gets old real quick. The Drybar is the original blow-dry-only hair salon and everything from the smell to the friendly vibe to the blow-dry make this a must. There are Drybars all over, and you can book online.

Los Angeles to Santa Barbara |2 hours

Santa Barbara beach bicycle

What to expect in Santa Barbara: A beautiful seaside town with more of those theme-park-perfect streets that I loved so much. The vibe is really laid back and the whole town feels like a holiday resort. There’s a loooong stretch of beach that’s just perfect for a bike ride or a walk and a quaint little harbour where clam chowder feels particularly mandatory.

Where to stay: We stayed at the stunning Hotel Californian, which is the perfect walking distance from pretty much everything there is to see and do in town. It’s got a very pretty Spanish Colonial aesthetic, and a rooftop pool complete with ocean views.

What to do in Santa Barbara

Cycle along the palmtree-lined beach front: It’s pretty laid back, so have a late breakfast and then grab a bicycle and take a ride to the beach to feel like you’re on a proper holiday.

Have lunch at the marina: The marina has such a great seaside vibe, perfect for a relaxing seafood lunch and a sunset spent watching the boats bobbing around on the water.

Santa Barbara to San Luis Obispo

& Paso Robles | 1,5 hours , 30 mins

madonna inn san Louis obispo california

What to expect in San Luis Obispo: Half way between LA and San Francisco! Known locally as SLO, it’s a University town with a strong wine culture. Beautiful wine country perfect for a day spent expanding on your tasting knowledge or just, you know, dinking wine.

Where to stay: We stayed at the Madonna Inn, which I very strongly recommend. It’s a crazy, bright pink, eyepopping hotel that has to be seen to be believed. Each and every room is different, but they are all pretty nuts. The food at the restaurant is so good, so don’t bother going out for dinner.

What to do in San Luis Obispo & Paso Robles

madonna inn California USA

Stop in Pismo Beach: For a cup of creamy, delicious clam chowder (man I really hope you like clam chowder or this whole list is going to be a real let-down) and saltwater toffee, which is not salted caramel, as I thought, but gets its name from the time, many years ago, when a taffee store was flooded by seawater. Even if you’re not particularly partial to clam chowder, Splash Café is known as the home of the stuff, so it might just change your mind.

Wine tasting: I love going wine tasting in different parts of the world and learning about new wines and winemaking techniques. We had a driver for the afternoon so there was no spitting, and we visited Venteux Vineyards and Brecon Estate, among others. It’s a really pretty part of the California Coast route, and so different from the rest of the trip.

Paso Robles to Big Sur | 3 hours

glamping Ventana big sur California

What to expect in Big Sur: Known as one of the most beautiful coastlines in the world and recently thrust into the pop culture spotlight thanks to an iconic shot in the opening credits of Big Little Lies, this was probably my favourite drive of the whole trip. Big Sur is a rugged section of coastline, dotted with incredible natural scenery, just waiting for you to cruise along with the windows open.

Where to stay: Ventana Big Sur is a luxury resort set between the giant redwoods, the mountains and the sea. It. is. beautiful! We stayed in a huge cabin complete with a jacuzzi overlooking the trees and a fireplace to keep our suite warm (all courtesy of The Blonde Abroad). There’s also a heated infinity pool and a stunning spa on the property, along with a top-class fine dining restaurant. Their glamping tents are what even the most next-level dreams are made of, with gas fireplaces and decor that makes the whole scene feel like it’s specifically set up for a photoshoot.

What to do in Big Sur

Image credit: The Blonde Abroad

McWay Falls at Julia Pfeiffer Burns State Park: You have to stop to see the beautiful McWay Falls. You can find them on Google Maps so make sure you do because otherwise it’s easy to drive past them – it’s definitely worth pulling over.

Monterey Bay: Another Big Little Lies location, Monterey Bay is home to a world-famous aquarium and a few nice restaurants and coffee shops.

Big Sur to San Francisco | 3 hours

usa road trip Twin Peaks San Fransisco

What to expect in San Francisco: An amazing city packed with people from all over the world! San Fransisco really made me feel at home, like I could live there. The food scene, the vibrant culture, I loved it all. Driving over the iconic Golden Gate bridge gave me butterflies and I would love to go back to spend more time exploring every single little side street.

Where to stay: We stayed in the Marina District, just at a little motel. It’s a great place to base yourself, with lots of restaurants and bars to duck into for after-dinner drinks. Exploring via car is a out of the question (the one time we decided to drive, we literally had to park our car as close as possible to the restaurant and then Uber to brunch anyway), so best to Uber. Also you’re in the city that invented Uber so it’s particularly novel.

What to do in San Francisco

golden gate bridge San Francisco

Lombard Street: It is twisty and turny and looks like a scene from an Alice in Wonderland fantasy.

Coit Tower: Mostly just for the views, which span the entire city in every direction.

Pier 39 + Fisherman’s Wharf: For a clam chowder bread bowl (it’s in a bread bowl this time!) and some souvenir shopping.

Buena Vista Café: Apparently the home of Irish Coffee. Like the place that invented it. It’s strong and delicious and very expensive but you’ve gotta do it!

Lyon Street Steps: Views, views, views!

Ghirardelli Ice Cream & Chocolate Shop: Don’t let the queues put you off. This place is a chocolate-lover’s dream! I had the biggest Sundae on the menu which gave me a stomach ache until Tuesday but that’s just cause my eyes are bigger than my stomach and it was worth it anyway and I  regret nothing.

Haight-Ashbury: Quintessential SF. It’s full of weird and wonderful characters and stores.

Twin Peaks: My favourite spot for views all the way to the Golden Gate Bridge and Alcatraz.

Painted Ladies: “Everywhere you look, everywhere you look”. If you grew up in the 80’s this iconic row of colourful houses will make your heart so happy! You’ll definitely know it from the opening credits of Full House.

This was the road trip of a lifetime and I highly recommend it! There’s so much more I still want to see and do in the US, so I’m so grateful that they’re finally issuing 10 year visas! See you soon, USA. Until next time x


  • Reply

    Michelle Edwards / 07 Sep

    Awesome! We are doing pretty much this route, but with a few extra stops, over 14 nights, in the US summer next year, so was very keen to see your recommendations on where to eat (clam chowder foreverrrrr), shop, stay, etc. We were planning on staying at the Pfeiffer State Park itself but your Ventana Big Sur camping just looks too good!

    • Reply

      natalie / 07 Sep

      I’m so jealous! I would have loved to spend more time on our trip! Don’t miss the Pismo Beach chowder – it was so good! The glamping at Ventana is SO AMAZING! Enjoy enjoy enjoy!

  • Reply

    Lalannie Knoll / 07 Sep

    Wow wow!! Once again you raised the bar! Your pics are stunning and the information note-worthy. Your outfits match all the scenes perfectly. Have yet to explore this continent and will definitely use this as a guide.

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