Everyone knows the world-class city of San Francisco and the high-tech hub Silicon Valley, but many miss the treasures in between. The San Francisco Peninsula is just a few miles south of the city, flanked by the Pacific Ocean and the SF Bay, with stunning mountains running up the middle. While it has a bunch of charming towns, San Mateo County and its many outdoor advocates had the foresight to protect 42% of its land, from beach coves to redwood groves.
That balance of urban sophistication and wilderness is what makes this region so special. We could catch a few waves in the morning, follow it with a Michelin-star lunch, hike in a state park in the afternoon, and take in an outdoor concert at a historic mansion in the evening. And when it comes to food, the San Francisco Peninsula takes its farm-to-table cuisine very seriously. They treasure their 50 local farms (many family-run, organic, and regenerative) and make the most of the culinary talent pool at their doorstep.
We will admit we’ve been to San Francisco a dozen times and taken multiple Pacific Coast Highway road trips, but we didn’t give the peninsula nearly enough time. There is a ton packed into this 450-square-mile area, so whether you are planning a city trip or a quick weekend getaway from the Bay Area, you don’t have to travel far to have a vacation, with both outdoor adventure and culture. Follow our San Francisco Peninsula road trip guide for the best things to do in San Mateo County, from the bayside to the coastside.
San Francisco Road Trip Itinerary
Drive just 12 miles south of the city and you’ll reach the coastal town of Pacifica. Cruise down the Pacific Coast Highway, stopping at as many vista points as possible on your way to the Fitzgerald Marine Reserve and Half Moon Bay. Cutting inland up the scenic Highway 92, you’ll get a taste of the peninsula’s many family farms, before zigzagging your way up the Santa Cruz Mountains. From here, you’ll rise above the marine layer and get views of the ocean and bay, plus the beautiful Upper Crystal Springs Reservoir. Next stop is Filoli Estate, a mansion on the National Historic Register and a nature preserve offering regular cultural events.
Continue to Woodside, one of the wealthiest but most understated towns in the country, with lots of history and nature to explore. If you have a hankering for more cosmopolitan recreation, you can easily head to the Bayside towns like Redwood City or Palo Alto. If the great outdoors still calls, zigzag your way through the various nature reserves back to the Coastside. Head south on the PCH towards Pescadero and make this region your base for small-town charm and a myriad of coastal adventures. On your return trip north, know that Pescadero is only 37 miles from SFO airport, so you can meander back, return a rental car, and still catch an afternoon flight.
PACIFICA
Leaving busy Highway 280 for the PCH, we felt the beach vibes coming our way. We saw multiple exits for Pacifica, which made us realize this little town is split into three sections, because the rugged coastline and dense forest keep it from continuous development. Love this place already. Northern Pacifica has a great little main street (Palmetto Ave) and an extensive pier packed with fishermen in action.
The middle section is almost pure nature, with fantastic coastal hikes and beach coves, and Southern Pacifica is where the city’s surfers live and play, with a great brewery, coffee shop (mmm Soul Grind), and one of the country’s few Taco Bells with a bar. It’s also home to the World Dog Surfing Competition, so even canines are catching waves here.
Though Pacifica is more than just a beach town, it holds a significant piece of California history with three Golden Gate Recreation Sites, including the Ohlone-Portola Heritage Site, where the San Francisco Bay was first discovered by Europeans in 1796. So whether you’re looking for culture, surf, or tacos, Pacifica is a great place to start your SF Peninsula road trip.
Things to Do in Pacifica, CA
Sánchez Adobe Park & Art Center
Sánchez Adobe showcases the first three periods of California History: Native American, Spanish, and Mexican. Enjoy the historic architecture and informative display, then continue a half mile up the road to the Sanchez Art Center for a taste of modern Pacifica. This community-run nonprofit gallery has beautiful works and fun receptions on First Fridays.
Hike Mori Point
This 2.6-mile loop trail in central Pacifica is a fantastic way to get the full perspective on the town and its natural beauty. Looking to the north, you can see the pier and even the Golden Gate Bridge on a clear day, and the sea cliffs are stunning. Be sure to linger at the point and peer through the community binoculars; there are always seabirds on the rocky islets, and we spotted four humpback whales! Tip: If you’re short on time, park on Fairway Drive and do Mori Point as a short out-and-back hike.
Surf Lesson at Pacifica State Beach
The gentle waves of this sweeping cove make it a great beginner’s beach, and there are plenty of solid surf schools to choose from, like Adventure Out and Surf Camp Pacifica. Even if you’re a land lubber, this beach is well worth a stroll to watch the surfers and admire the quirky coastal cabins that stack the hillside.
Margaritas at Taco Bell?
Of the 8,000 Taco Bells in the USA, there is only one that is beachfront with a bar. As vegans, Taco Bell is one of the few chain restaurants where we can get a decent plant-based meal, and when you add a margarita and ocean view, it tastes twice as good. Grab a seat on the patio and watch the surfers ride in for chulupas and cervezas.
Tidepool at JV Fitzgerald Marine Reserve
Within the Monterey Bay National Marine Sanctuary, this exceptionally biodiverse section of coastline is a tidepooler’s paradise. In fact, in our “Best-in-Class Beaches” section of our Nat Geo book, we featured Moss Beach as our #1 pick for tidepooling! When we went this August, it was full of newborn harbor seals, so the beach was closed, but spotting these cuties from the cliffs was still worth it. While just down the road, Ross Cove has fantastic tidepools, teeming with sea anemones, starfish, hermit crabs, and colorful kelp. Just be mindful of where you step in this fragile habitat and leave no trace.
Where to Stay Pacifica
Anchor Inn
We loved our stay in these sleek, tiny houses. With a full kitchen, airy living room, and wrap-around porch overlooking Pacifica State Beach, Anchor Inn had everything we needed in our studio, and we loved that it was just a 5-minute walk to the beach, brewery, and the best coffee shop in town.
HALF MOON BAY
Cruising down the Pacific Coast Highway, just 10 miles south of Pacifica, is one of the oldest and quaintest communities in San Mateo County. The Ohlone Native Americans lived here for 14,000 years, then Spain’s colony of Mexico established the town as San Benito. When the Gold Rush hit, it became known as Half Moon Bay, and its ports and railways were pivotal in supporting California’s booming economy. Walking Main Street today, 19th-century buildings house charming boutiques and restaurants, and many of their walls are adorned with murals.
See the Francis Building for a painted depiction of the town’s history, and don’t miss the homage to Mavericks, a HMB surf break with 100-foot-tall waves and home to the world’s preeminent big wave surf contest. Beyond the Old Town, Pillar Point Harbor is another hub of activity with watersport rentals, breweries, and restaurants. Go inland, and you’ll find lovely family farms that welcome visitors with fresh produce and agrotourism activities galore, especially in the fall.
Things to Do in Half Moon Bay
Shop Main Street HMB
There are so many local makers and purveyors on Main Street. Be sure to shop stores like Fish Wife for sweets, Home Town for chic decor, and Cruiser Clothing for unique, locally designed surfwear and Highway 1 souvenirs.
Kayak Pillar Point Harbor
We almost let a bit of rain and fog keep us from heading out with Half Moon Bay Kayak, but it turns out it’s always a great day to paddle at Pillar Point Harbor. Heading out to the jetty, we literally saw 1,000+ pelicans diving, preening, and huddling up on the rocks. That wildlife experience alone is worth the trip, but continue north into the outer harbor and you’ll find a sunken World War II era tugboat you can splash around. And if you have our luck, you may even find yourself in the middle of a colorful regatta.
Train-car Dining at Dad’s Luncheonette
Michelin-starred chef and author of the new Coastal Cookbook brings fine dining quality to classic American fare with the nostalgic Dad’s Luchonette. Set in a century-old caboose, this lunch-only restaurant (open Thursday-Sunday) is a local treasure.
Sunset Drinks at The Ritz Carlton Half Moon Bay
We wouldn’t normally recommend the Ritz, but the resort’s spot on sea cliffs and sunset views are well worth it. Dress up, arrive an hour before sunset to secure a good spot on the balcony, and toast to a fabulous day in Half Moon Bay.
Where to Stay in Half Moon Bay
Nantucket Whale Inn
Located just off Main Street in a Victorian farmhouse, this seven-room inn is so chic and inviting. With amenities like included breakfast, reliable wifi, an outdoor living room, a complimentary evening wine bar, and downtown right out your front door, you will be perfectly situated at this award-winning boutique hotel.
HIGHWAY 92
While it’s tempting to keep cruising the jaw-dropping Pacific Coast Highway, it’s worth ducking into the Santa Cruz Mountains for the big picture on the San Francisco Peninsula. Starting up Highway 92, you’ll be surrounded by quaint family farms (come fall, this place is pumpkin mania!). Hop out at Pastorino’s for a series of farmstands and boutiques from Highway 92 Succulents to the fragrant Half Moon Bay Lavender.
Continue up the switchbacks into the sunshine, and you’ll get glimpses of the San Francisco Bay and its string of Bayside towns. Highway 92 turns into Cañada Road and hugs the beautiful Upper Crystal Springs Reservoir. It was so pretty, we hopped out for multiple photo ops of this vast water source on our way to Woodside.
WOODSIDE
Home to many of Silicon Valley’s CEOs and executives, Woodside is among the wealthiest small towns in America. But you wouldn’t know it when you pass the Gold-Rush-era saloon, see cowboys riding on horseback, hike the redwoods of Purisima Open Space, and eat at Buck’s greasy spoon. Woodside also neighbors Stanford University, but it’s so serene here that you also wouldn’t know there was a college campus nearby. Clearly, Woodside took us by surprise, and we were so glad we added it to our route…particularly with one of our favorite stops on our San Francisco Peninsula Road trip, Filoli Estate!
Things to Do in Woodside
Poke around The Historic Woodside Store
The town’s 1850s mercantile and post office is on the National Register of Historic Places for being a significant example of California’s early American settlement. Head into their free museum to learn about Woodside’s days as a lumber mill town that helped develop the Bay Area during the Gold Rush. Open Tuesday, Thursday, Saturday, and Sunday, it has limited hours, but poking around the redwood buildings and peering into the mercantile is still worth a stop any day of the week.
Eat like a Silicon Valley Mogul at Buck’s
Despite its kitschy decor, this diner is where many of Silicon Valley’s pivotal venture capital meetings have taken place, from Netscape to Tesla. In addition to serving grub good enough for Warren Buffett and Yahoo’s cofounders, Buck’s is a mini museum to Silicon Valley and the restaurant owner’s wild imagination, displaying everything from a 1976 Apple 1 computer to a 300-piece collection of Cracker Jack prizes, all under a ceiling of dangling astronauts and alligators riding a surfboard.
Forest Bathing at Purisima Creek Redwoods
Drive six miles up the forested Kings Mountain Road, with curves that hug the redwoods, and you’ll reach this 4,471-acre open space preserve. With the help of its wealthy neighbors, Save The Redwoods League raised 2 million dollars to protect this grove and develop trails and picnic areas to breathe in the trees and soak up the sounds of the creek. Hikes range from 1-10 miles, so pick your distance and forest bathe.
Filoli Estate & Nature Preserve
@honeytrek Hidden in the mountains of the San Francisco Peninsula, the Filoli historic estate on 600+ acres with formal gardens and redwood groves is stunning and so much fun! We went for their Summer Nights concert series and “Trolls: Save the Humans” exhibit, by one of the world’s premier recycle artists. Watch the magic of Filoli. @Filoli Historic House & Garden @The San Francisco Peninsula #partner @Thomas Dambo #filoli #sfpeninsula ♬ Little Sparrow – Paul Alan Morris
Historic homes can feel staged and stuffy—not Filoli. This 54,000-square-foot Georgian Revival mansion is not only beautiful, with its fresco-clad ballroom and 16 acres of English gardens, but it’s also a robust nature preserve and cultural center. Totalling 654 rolling acres, the formal gardens fade into wilderness with extensive trails, enhanced by art exhibits and music performances.
We went for Filoli Summer Nights, which featured two music stages, food trucks, lawn games, and guided sunset hikes. While Summer Nights is wrapping up for the season, fall has tons of cultural programs, including the incredible “Trolls: Save the Humans” exhibit by the world’s premier recycle artist, Thomas Dambo. Until November 10, 2025, six of these giant reclaimed wood sculptures are scattered around the property, each telling a story about conservation through whimsy and wonderment. Watch our TikTok for a dash of Filoli’s magic.
Where to Stay in Woodside
Canyon Ranch Woodside
Stay like the rich and famous with a restorative getaway at Canyon Ranch Woodside. This renowned, five-star health resort is pricey, but its spa services, farm-to-table cuisine, and wellness workshops will make you feel like a million bucks.
HIGHWAY 84
The SF Peninsula road trip continues along Highway 84 to the coast. Enjoy the mountain ride and stretch your legs at La Honda Creek Open Space Preserve or Sam McDonald, an 850-acre reserve with its two distinct ecosystems of redwood grove and grassy knolls, with views to the Pacific. When you return to Highway 1, hang a left toward Pescadero.
PESCADERO
The Spanish word for fishing place, Pescadero, might make you think it’s on the ocean. Instead, these clever 19th-century fisherfolk went a little inland for warmer weather and gentler winds. Established in 1856, Pescadero boasts many historic buildings, including the Victorian Community Church and the Dickerman Barn, both of which are listed on the National Register of Historic Places. This 500-person town is still a fishing, farming, and ranching community, now with a touch of hipster and lots of local pride.
Things to Do in Pescadero
Nibble Down Stage Road
Pescadero’s main street is small but mighty, with purveyors like Sunshine Coastal Farm Shop selling everything from pickling spices to vinyl records. Grab a great cup of coffee from their espresso bar, then continue down the block to the historic Arcangeli Grocery for their famous artichoke bread and homemade spreads. Finish off your strolling smorgasbord with dinner and cocktails at Duarte’s Tavern, “where friends meet, est. 1894.”
Farmstead Tour at Harley Farms
On the outskirts of Pescadero is a 1910 dairy farm, with 200 alpine goats and the loveliest owners. We went inside the Harleys’ farm shop and chatted with Dee (a Brit who married into this fourth-generation Pescadero family) for an hour about their recent gold medal at the World Cheese Show and her aspirations to offer glamping accommodations. Join their weekend Farmstead Cheese Tour, where you can watch the process of their traditional cheese making and even milk a goat, and check their calendar of events for their famed hayloft dinners and Hallowed Eve party.
Pigeon Point Lighthouse
Whether driving the PCH or sailing the Pacific, you can see the 115-foot-tall Pigeon Point Lighthouse for miles; it has guided travelers to (or away from) its shores since 1872. Walk to the point to enjoy America’s third-tallest lighthouse, its informative museum, and sweeping views up the coast. To truly commune with this piece of history, you can stay the night. Hosteling International offers private rooms and a cliffside hot tub on Pigeon Point’s bluffs!
Wildlife Watch at Año Nuevo State Park
This is one of our favorite California State Parks! Starting at Año Nuevo’s wonderful visitor center, in a 19th-century dairy barn, learn about everything from the coastal homesteaders to the 10,000 elephant seals that call this park home. December-March is primetime to see their breeding rituals and when the reserve leads guided walks, and it’s always worth the 3-mile RT hike to Año Nuevo Point, since there’s always at least a few 5,000-pounders lying around or battling it out on the beach. We’d also highly recommend the Franklin Point Trail to see the park’s range of ecosystems from coastal terrace prairie, wetland marshes, dune fields, and gorgeous beach coves.
Work Day and Barn Dance at Pie Ranch
With far bigger aspirations than broccoli and baked goods, Pie Ranch cultivates a healthy and just food system through its teen educational programs, land for BIPOC farmers, native plant program stewarded by the Amah Mutsun Tribal Band, and so many fun events. Stop in for a slice of pie and an educational walk around the farm, and if you can time your visit with the third Saturday Work Day & Barn Dance, you will have a perma(culture) smile on your face.
Lend the farmers a hand in the Native Garden for a few hours, then get discounted entry to their square-dance spectacular. We’re not great at dancing, but with their expert caller, bluegrass band, and the fun-loving vibes of Pie Ranchers, we were do-si-doeing with the best of them!
Where to Stay in Pescadero
Costanoa
With over 100 acres overlooking Año Nuevo State Park and the Santa Cruz Mountains, this glampground is in a coveted location and makes the most of it. Choose from their wide range of lodging (hotel rooms, cabins, glamping tents, or RV park), and settle into the village with its two restaurants, a country store, spa, robust activity center, and trail network. We thought Costanoa was lovely as is, but a little birdy told us they are about to do a major renovation of the lodge and restaurant for an even better getaway.
End of the San Francisco Peninsula Road Trip
We hope you have a blast on this road trip, and if you’re looking for more great stops on a return trip north, be sure to hit Martin’s Beach for its dramatic sea stacks and Bean Hollow State Beach for our favorite picnic spot, and check out the region’s calendar of events. Before you leave the peninsula, treat yourself to one last farm-to-table meal (we loved the plant-based Twelevemonth in Burlingame) and raise a glass to a great San Francisco Peninsula Road Trip!
Note: Many thanks to the San Francisco Peninsula Tourism Board for inviting us to explore their region. As always, all opinions are our own, and we only share what we truly love with you guys. See you on the road!
