Some of the best road trips begin the moment the wheels touch down. My recent journey from San Francisco International Airport to Sonoma wine country was exactly that kind of trip — one that started with a legendary Silicon Valley lunch spot, wound through one of the world’s most iconic bridges, made a gelato detour in a bayside village, and ended with three very different wineries and some truly memorable Pinot Noirs.
Lunch First: Buck’s of Woodside
My friend picked me up at San Francisco International, and before heading north toward Sonoma, we made a detour south into the hills of San Mateo County for lunch at Buck’s of Woodside. If you’ve never heard of it, here’s the short version: this quirky, knick-knack-stuffed diner on Woodside Road has been a fixture of Silicon Valley since 1991. The walls are plastered with an eclectic collection of oddities, and a 20-foot carved wooden fish marks the entrance out front, and astronauts are inside.
But Buck’s is more than just a conversation piece. This is where some of the biggest deals in tech history were reportedly hammered out over breakfast. Meetings for many of the internet giants happened at these tables. Founder Jamis MacNiven built something genuinely one-of-a-kind here, and his sons now carry on the tradition.
The food is solid American comfort. I had a Cobb salad with chicken. It was the perfect meal after a long flight. Whether you’re a Silicon Valley history buff or just hungry, Buck’s is worth it. It’s the kind of place that feels like it couldn’t exist anywhere else in the world.
Over the Golden Gate
The drive north takes you through San Francisco and across the Golden Gate Bridge — and no matter how many times you’ve done it, crossing that bridge still does something to you. The rust-colored towers rose into a beautiful but windy Bay Area day. The views were spectacular. It’s one of those rare moments where the road itself feels like the destination.
The Golden Gate has been carrying travelers north toward wine country since it opened in 1937, and crossing it still feels like a portal into redwoods and vineyards.
A Sweet Stop in Sausalito
Just on the other side of the bridge, we pulled off into Sausalito. This charming bayside town has been luring day-trippers from San Francisco for generations. The waterfront along Bridgeway faces back across the bay toward the San Francisco skyline, with sailboats drifting past. It’s picture-perfect.
We stopped at Atalia Gelato and Chocolate. It seemed to beckon us when my friend mentioned he’d like some gelato during the trip. Here was our chance. They make small-batch artisan chocolates alongside creative gelato flavors like blueberry ricotta and pistachio ricotta. We shared a small dish of salted caramel. A perfect start to our trip.
Into Wine Country: The Sonoma Wine Pass
By the time we reached the Hilton Garden Inn in Sonoma, the small town at the heart of the Russian River Valley. We purchased a one-day Sonoma County Tasting Pass, one of the smartest ways to explore the wineries. This gives you the ability to experience up to four exclusive tasting offers at some of the region’s best wineries in a cost-effective way.
We decided to focus on Pinot Noir at each stop, since the Russian River Valley has earned its reputation as one of the world’s great Pinot Noir regions. The AVA was officially established in 1983, though winemakers were working this land as far back as the 1870s.
All three wineries we visited sit along Westside Road, one of the most scenic drives in all of California wine country. Here’s how our day unfolded.
Twomey Winery
Twomey was the first stop of the day and, as it turned out, the favorite of the day. Founded in 1999 by the Duncan brothers, the same family behind the legendary Silver Oak Cellars. Twomey takes its name from the family’s grandmother, Velma Twomey Duncan. It’s a personal touch that sets the tone for everything here.
The tasting room is a striking piece of architecture: glass walls, a curved roofline that follows the contours of the surrounding hillside, and sweeping panoramic views. Stepping inside feels like stepping into the landscape itself.
What made Twomey stand out wasn’t just the views or the wines; it was the people. Our tasting host, Romana, was generous with history and information, explaining the stories behind each vineyard and vintage in a way that made every glass more interesting. The Pinot Noirs were the best we tasted all day, layered, elegant, and expressive of the Russian River Valley terroir in the best possible way. If you only have time for one stop on Westside Road, make it this one. Tastings from $35/person
Gary Farrell
Gary Farrell Winery sits higher on the ridge than Twomey, and the views from their hilltop tasting room are nothing short of spectacular. On a clear day, you can see the entire Russian River Valley spread out below you. It’s one of the most beautiful settings in Sonoma County, full stop.
The winery has serious credentials: founded in 1982, Gary Farrell helped put Russian River Valley Pinot Noir and Chardonnay on the world map, and the winery was named a Top 100 Winery by Wine & Spirits Magazine two years running.
Honestly? The location may be the star here. The views alone make the visit worthwhile, and the wines are certainly well-regarded by critics. For our palates on this particular day, though, the Pinot Noirs didn’t quite match the drama of the setting. Your experience may differ — wine tasting is personal, and Gary Farrell has no shortage of devoted fans. But if you’re coming to Healdsburg, the drive up to their overlook is reason enough to stop.
Lunch Break: Big John’s Market
Between wineries, we stopped for lunch at Big John’s Market on Healdsburg Avenue. It was a perfect suggestion, and I’d tell every wine country visitor to do the same. This family-owned specialty market/grocery is the real deal: made-to-order sandwiches, a hot bar, an outstanding cheese counter, fresh sushi, and a local wine selection that reflects the best of the region. We had freshly made turkey sandwiches and shared some pasta salad.
It’s the kind of market that makes you wish you lived nearby. Open daily from 7 am to 8 pm, it’s perfectly positioned for a midday break between tastings.
Russian River Vineyards
The last stop of the day was Russian River Vineyards, and it delivered something the other two didn’t quite have: pure, unhurried ease. This is a laid-back, friendly tasting room. No pretension, no performance, just good people pouring good wine.
The Pinot Noirs are approachable and enjoyable. If you’re new to wine country and worried about feeling out of your depth, come here first. The atmosphere is welcoming to everyone, from seasoned collectors to first-time visitors. It’s a wonderful way to end an afternoon — relaxed, easy, and genuinely warm.
Was the Wine Pass Worth It?
Absolutely! It saved us about $50 on our tastings. The Sonoma County Tasting Pass made it easy to visit multiple wineries without the usual mental math about tasting fees. It can easily pay for itself on a weekend trip like this one.
Sonoma wine country can feel overwhelming to plan. There are hundreds of wineries, and tasting fees add up fast. A pass like this lets you focus on the experience rather than the expense. My advice: anchor your day around Westside Road, leave time for a proper lunch at Big John’s, and save Twomey for when your palate is fresh.
After a full day of wine tasting, we opted for dinner near the hotel. Carmen’s Burger Bar. It was tasty food at a reasonable price, with great service.
Day Two: A Blind Tasting, Aviation History, and Dinner in Railroad Square
If Day One was about the road, Day Two was about going deep. One remarkable winery experience that lasted four hours, a stop at an approachable aviation museum, and dinner in one of Santa Rosa’s most atmospheric dining rooms.
The Main Event: DeLoach Vineyards
We could have spent the entire day at DeLoach Vineyards and nearly did. We were there for four hours, and not a minute felt wasted.
DeLoach is one of the founding stories of Russian River Valley winemaking. Founded in 1975, it holds the distinction of being the first winery to plant Pinot Noir on the Olivet Bench and the first to put the Russian River Valley appellation on a wine label. Fifty years later, it’s still one of the most distinctive estates in Sonoma County — a certified organic, Demeter-certified Biodynamic 20-acre farm on Olivet Road in Santa Rosa, with a working culinary garden, fruit trees, farm animals, and vineyard blocks all woven together on the property.
The highlight of our visit was the blind tasting of French and American wines. It was genuinely one of the most educational wine experiences I’ve had. Jeannette, the tasting manager, suggested the blind tasting. She helped make it memorable with her knowledge and educated us on how to better understand the wine.
The Blind Tasting
DeLoach’s signature blind tasting pits French wines from their Boisset family partner estates against their California counterparts, comparing Chardonnays and Pinot Noirs from Burgundy alongside those from the Russian River Valley. Without labels to guide you, you’re left with only what’s in the glass. The result surprised us. The French wines won the day. There’s something about the restraint and earthy complexity of a Burgundian Pinot Noir that stands out when you’re tasting blind. It was a humbling and genuinely fun exercise, and one I’d recommend to any wine lover who thinks they already know what they prefer.
The experience lasts well beyond a standard tasting. Jeanette guided us through the wines with real depth, sharing the stories behind the vineyards and the winemaking philosophy that drives everything here. DeLoach’s commitment to biodynamic farming — meaning they follow natural farming cycles, avoid synthetic inputs, and treat the land as a living ecosystem — comes through not just in the wines but in the estate’s whole atmosphere. Walking the grounds, you feel it.
If you visit, build in more time than you think you’ll need. This is not a pour-and-move-on kind of place. It rewards patience and curiosity, and the staff is genuinely delighted when visitors want to dig deeper. My friend, who lives in Sacramento, even joined the wine club! This is definately a place I would return to.
Pacific Coast Air Museum
Regular readers know I can’t resist an aviation museum, and Sonoma County has a good one. The Pacific Coast Air Museum sits right on the grounds of Charles M. Schulz–Sonoma County Airport in Santa Rosa, and it’s a genuine find for anyone who loves flight history.
Founded in 1989, the museum displays more than 35 historic military aircraft across a five-acre outdoor campus, ranging from World War II-era propeller planes to Cold War-era jets. The museum is smaller than the big-name aviation museums you may have visited elsewhere, but don’t let the size fool you. What it lacks in scale it makes up for in character. The volunteer docents are the real draw. They are knowledgeable, enthusiastic, and full of stories that bring each aircraft to life in a way that a placard never could. The aircraft themselves are a fascinating mix, ranging from World War II-era propeller planes to Cold War jets, and the display boards are unusually detailed, covering everything from design specs to the individual history of each specific airframe.
One of the aircraft on display is an F-15 Eagle that was among the first jets over New York City on September 11, 2001. Each plane has its own story, and the museum tells those stories well.
Admission is just $10 for adults — exceptional value for what you get. Aviation enthusiasts, budget considerably longer.
Dinner: Stark’s Steak & Seafood
After a full day of wine and history, dinner at Stark’s Steak & Seafood in Santa Rosa’s Railroad Square was exactly the right call. The restaurant occupies a 1892 landmark building — all polished wood, red lighting, white linens, and a quiet energy that sits somewhere between a neighborhood steakhouse and a special-occasion restaurant.
Stark’s is serious about its meat. Alongside the steaks, the menu features sustainable seafood, and the wine list is deep in both California and European bottles, with many available by the half-bottle. A thoughtful touch for wine country visitors who’ve already been tasting all day.
We caught happy hour — and it lived up to its reputation as the best in Sonoma County. The bar menu is a serious value: think prime rib banh mi sandwiches, crispy calamari, ahi tartare tacos, oysters, and truffle fries, all at a fraction of the prices on the dinner menu. The atmosphere delivers too — polished wood, red lighting, white linens, and a warm buzz that makes it easy to linger. After a full day of wine tasting and aviation history, it was the perfect way to end the evening.
Saying Au revoir to Sonoma, and things go sideways
Two days, two very different paces, and both worth every mile. Whether you’re mapping out a wine country road trip from scratch or looking to fill a second day in Sonoma with something beyond the tasting room circuit, this combination of a world-class blind tasting, a bit of aviation history, and a great dinner in downtown Santa Rosa is hard to beat.
We had plans to visit more wineries, but fate intervened. Be sure to read my next post on what to do when things go a little sideways.
The Road Continues: Sacramento
From vineyard roads to wide boulevards, the journey continued east to a city that often surprises first-time visitors. I stayed at the Holiday Inn Rancho Cordova, a comfortable and well-positioned home base for getting around the capital region.
First stop: the State Capitol. California’s political story unfolds beneath that iconic dome, and it’s a more compelling place than you might expect — both a working government building and a window into the state’s long and complicated past. The architecture alone is worth an hour of your time. The Leland Stanford Mansion, which served as the Governor’s residence and the state’s official reception center. This beautiful Victorian beauty is located just blocks from the statehouse.
From there, Sacramento’s museum scene adds real texture to the trip. The Aerospace Museum of California is a deep dive into flight and innovation that moves faster than you’d expect — there’s genuine wonder in there. The California Automobile Museum tells the story of motion on the ground, tracing how cars shaped California culture as much as California shaped car culture.
Put them together and an interesting thread runs through the whole journey: how Californians have always been obsessed with moving — by road, by air, and through history. From Sonoma’s vineyard-lined back roads to Sacramento’s wide boulevards, the state keeps revealing new layers the further you go.
Sacramento sits right at the center of that story. It’s well worth the drive to find out for yourself.
Final Thoughts
What begins as a simple wine country getaway quickly becomes something more layered.
From Silicon Valley’s deal-making tables to Sonoma’s vineyards, from vintage aircraft to California’s seat of government—this journey reveals a different side of Northern California.
It’s not just about where you go—it’s about the stories waiting there when you arrive.
There are some YouTube videos interspersed in this post of the places we visited. Be sure to check out my travel videos at RRJ
