A road trip to the best urban experiences in California

California is rightfully praised for its natural wonders, from the crashing pacific to the towering redwoods and jaw-dropping granite peaks of Yosemite. But just as impressive in their own way are the Golden State’s dynamic cities – as diverse and exciting as any in the U.S.

One of the world's great cultural cities, Los Angeles, is a hotbed for the arts and an extraordinary melting pot of cultures in an incomparably beautiful setting. San Diego is known for its beaches and craft beer. And San Francisco keeps pushing boundaries with trendsetting food, social movements, art and technology.

Starting there, where the Golden Gate Bridge beckons, let’s hit the road for an exploration of some of California’s coolest cities – both well-known and off the beaten path. As our traveling companion, we have Annmarie Wong, a San Francisco-based influencer and transit/mobility advocate, who has amassed more than 26,000 followers to her @traingirlsummer account on TikTok; followers love her advice about public transportation in the Bay Area and other cities. With her expert advice on the urban sights worth seeing, here’s a city-focused road trip through Northern California that will inspire your next adventure on the open road – plus suggestions for amazing urban sights in other parts of the state.

The City by the Bay

Start your exploration in San Francisco, where you won’t need a car at all for the first day or two as you take in all the “city by the bay” has to offer. Wong’s specialty is transit, and she loves that most of the city’s top sights are well-connected by public options (or have nearby bike-share stations), making it easy to cut down your carbon footprint before the rest of your road trip.

Your first stop should be one of the city’s historic buildings: the Ferry Building is an essential landmark, and one of the few buildings that survived both the 1906 and 1989 earthquakes that rocked San Francisco. Nearby, the “floating” Salesforce Park is an oasis of calm and greenery surrounded by city hustle and bustle; it sits atop a major transit center, making it a great place from which to explore other parts of the city. “This is where nature and urban planning come together,” Wong says.

Next, be sure to visit Little Italy. It’s the place for authentic Italian dishes in San Francisco, but Wong also loves it for its inclusion in many movies, including Mrs. Doubtfire, Star Trek IV: The Voyage Home, and Zodiac. Little Italy connects to Chinatown, another must-see culturally rich neighborhood. It’s the largest and oldest Chinatown outside Asia, with some of the highest urban density in the country. Dumplings and rare teas are served under pagoda roofs on the main streets – but its historic back alleys are filled with temple incense and mah-jongg tile clatter. “Community and culture are very important and the city continues to preserve its history and art until this day,” Wong says.

Be sure to visit the Presidio Tunnel Top Park – a brand-new addition to this very park-friendly city (there are more than 200 in the 49-square-mile metropolis). From here, you can admire views of the Presidio and Golden Gate Bridge.

“It’s perfect for a picnic, and people – or dog – watching,” Wong says.

When you’re ready hit the road, prepare for one of the most iconic California road trip experiences of all. As you head north out of San Francisco you’ll cross the Golden Gate Bridge – the instantly-recognizable engineering marvel and one of the most-visited parts of the National Park Service system. Just across the bridge, the small town of Sausalito has a distinctly European vibe with al fresco dining options and a walkable Old Town. Stop to admire the Waldo Point Floating Homes, another Sausalito claim to fame – and once home to famous residents like writer Shel Silverstein and musician Otis Redding.

California’s capital city

Chosen at a time when the urban landscape of California was very different, Sacramento is a fascinating and historic state capital. With so much history, there are plenty of special sites, including the Capitol building itself, where visitors can tour the halls of state government. Elsewhere in the city, new lofts and upscale boutiques squeeze between mid-century storefronts.

Sacramento locals are a resourceful lot that have fostered small but thriving food, art and nightlife scenes. They rightfully crow about Second Saturday, the Midtown gallery hop that takes place in the summer months, that is the symbol of the city’s cultural awakening. Their ubiquitous farmers markets, farm-to-fork fare and craft beers are another point of pride.

Sacramento is also home to the Old Sacramento State Historic Park, which is part shopping and dining district and part interactive history museum with original buildings and other relics from chapters in the city’s bygone boom days. Nearby, the Tower Bridge is an iconic spot for a photo.

If you skipped the wine train in wine country, there’s another option here: Sacramento is home to its own “Old Vine Express” which runs along the Sacramento River. For a more active and/or less indulgent option, Wong recommends renting Railbikes – a fun four-wheeled vehicle that sits on rail lines, to ride along the rails instead.

The Central Valley and San Jose

South of Sacramento is California’s Central Valley, a largely agricultural region between the big cities of Sacramento and San Jose. As you make your way south, swing through the midsized city of Stockton. Two noteworthy stops here are the Historic Bob Hope Theatre, which dates to the 1930s and is one of the best remaining examples of Spanish Colonial Revival-style theaters, and the Wat Dhammararam Buddhist Temple, which was founded by Cambodian refugees who settled in this part of California and built the large Buddha statues that dot the landscape.

Coming back into the Bay Area and looping around to finish your urban-focused road trip back in San Francisco, you’ll pass through San Jose which sits in the “South Bay.”

This city is worth at least an overnight stop, as there are plenty of fascinating areas to explore. Base yourself near San Petro Square Market with its trendy restaurants and walkable streets; the nearby SoFa District (South of First Area) is home to wonderful museums and murals. Another option is the more recently developed Santana Row, which has plenty of shopping and nice restaurants in a small urban core.

Also in San Jose, the historic Winchester Mystery House is one of those tourist destinations that’s interesting enough to be worth admission. This ridiculous Victorian mansion is filled with 160 mostly non-utilitarian rooms with dead-end hallways and a staircase that runs up to a ceiling. Sarah Winchester – heir to the Winchester-rifle fortune – spent 38 years constructing this mammoth white elephant. No expense was spared in the construction, the extreme results of which sprawl over 4 acres. Apparently, it was commissioned because she claimed the spirits of the people killed by Winchester rifles told her to.

From San Jose it’s a short drive back up to San Francisco, and on to your next adventure.

Other California city experiences

To explore even more of the urban side of the Golden State, there are plenty of great options.

Los Angeles: No sampling of California cities would be complete without including the City of Angels. It’s the largest city by population and home to more than 12 million people in the greater urban area. There are countless great sights that show off what makes Los Angeles special. Silver screen dreams come alive beneath the iconic Hollywood Sign, and if you’re in that area, be sure to visit nearby Griffith Observatory for outstanding views over the city. The Hollywood Walk of Fame is also an essential spot for stargazers or those dreaming of their own chance at celebrity. For cuisine, Los Angeles is a true melting pot, with diverse and ultra-fresh options in abundance.

Southern California is also renowned for its beach culture. The sunsets in SoCal are incredible, so be sure to plan some time strolling along Venice Beach; there you’ll find locals hawking handmade art, bodybuilders getting beach-ready, and families headed to the nearby Santa Monica Pier to chase thrills on the rollercoasters and rides.

San Diego: Further south down the Pacific Coast, San Diego is another unique urban experience in California. Wong has some favorite spots here too: the city’s Old Town is home to the first European settlement in what would become California – and has the old shops, historic sites, and Spanish-influenced Mexican heritage to prove it. San Diego’s Little Italy is another area worth exploring, with its pedestrian-friendly streets and al fresco dining options.

If you’re in the car with little ones who need to burn off energy, Balboa Park is home to family-friendly activities, including the world-renowned San Diego Zoo, San Diego Air & Space Museum, and San Diego Model Railroad Museum (a favorite for Wong, the self-proclaimed “Train Girl.”).

Gold Country: For something completely different, extend your Northern California itinerary to hit the historic cities in California’s Gold Country. These snapshots of the past show what life was like before the highways and towering skyscrapers dominated California’s urban areas – the gold brought out of the western Sierra Nevada Mountains helped build those cities!

California Highway 49 (so named for the year of the state’s most productive gold rush) runs through a string of small towns with big history; be sure to stop at the Marshall Gold Discovery Museum (near Coloma), and the Kennedy Gold Mine (near Jackson) for a deeply interactive experience. Railtown 1897 State Historic Park (near Jamestown) is also a good spot to stretch your legs, especially if, like Wong, you love trains.

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