Best Itinerary for a Weekend in Sonoma Valley

Today I want to bring you my itinerary for spending a weekend in Sonoma Valley. This part of Northern California’s wine country is a fun place to go tasting, explore local towns like Glen Ellen, and soak up the scenery on Moon Mountain. If you have the chance to spend a weekend here, you’ll be able to experience everything from the vineyards that make this place famous to the towns locals love. I’m here now and I’m excited to show you the highlights of the region. I’ve included a map, too.

Weekend in Sonoma Valley

Sonoma Valley is one of my favorite places to visit in California. Not only does this place have world-class vineyards, but also historic towns and stunning mountain scenery. There’s something for every visitor here.

I know this from personal experience. I grew up in the Bay Area, I’ve been visiting Sonoma County my whole life. My trips have allowed me to see both the big attractions and the places locals love.

This time I’m spending a weekend in Sonoma Valley with my other half and a big group of family and friends. We’re excited to go back to some of our favorite places and explore a few new ones. Given how much we all love visiting wine country, we know it’s going to be good trip.

Friday Evening

My other half and I arrive in Sonoma Valley on a Friday evening after a drive from San Francisco. Traffic isn’t too bad, and we make it to Glen Ellen in around 90 minutes.

Where to Stay

Our whole group is staying at the Olea Hotel in Glen Ellen. We’ve taken over most of the rooms at this secluded boutique property, and we’re excited to call it home-away-from-home for the weekend.

The Olea Hotel is tucked away on a hillside just outside the main part of town. With spacious guest rooms, oak-canopied outdoor seating areas, a sun-drenched lawn with a fire pit, and a welcoming swimming pool, it has everything we love about a wine country hotel.

Including the price point. Accommodation in Sonoma Valley can be eye-wateringly expensive, and this place strikes a good balance between price and quality. If you want to follow in our footsteps, you can book a room here.

Happy Hour

We kick off our weekend in Sonoma Valley with happy hour by the fire pit at the hotel. We’ve picked up wine and cheese at Glen Ellen Village Market, and we all gather around to toast to a fun trip ahead.

Dinner

Later we make the 20-minute drive to dinner at Wit & Wisdom, a restaurant in the town of Sonoma. Situated in The Lodge at Sonoma Resort, this place is run by acclaimed chef Michael Mina.

Wit & Wisdom has a stylish interior complete with high ceilings, an open kitchen, and contemporary decor. The menu features regional California cuisine cooked on a hearth oven, and there’s a great wine list.

We settle in for a delicious meal as the dining room buzzes around us. It’s a fun way to spend the evening, and an ideal spot to officially start our weekend in Sonoma Valley.

Saturday

The next morning we enjoy a full cooked breakfast at the Olea Hotel. There’s both a buffet and a complimentary menu for guests to order from, and we tuck into everything from veggie croissant sandwiches to quiches and fresh fruit. It’s a generous offering, and a delicious way to start a Saturday in wine country.

Glen Ellen

After breakfast a few of us head into Glen Ellen to explore. It’s a small town near Jack London State Historic Park, and the main street is lined with heritage buildings that have an Old West feel.

The Sonoma and Calabasas creeks run through the heart of town. We walk across a bridge, admiring the views of the water below. From there we take in the shopfronts and historic saloon before heading back to our cars to head to the next stop on our itinerary.

Sonoma Plaza

Along with some others in our group, we drive to Sonoma Plaza to walk around and explore the shops. This famous square is lined with all kinds of tasting rooms, boutiques, restaurants, and cafes. It’s also known for its landmarks, including the historic Mission San Francisco Solano in Sonoma State Historic Park.

We can’t help wandering into the pretty courtyards, shopping for homewares at Chateau Sonoma, and taking in the scene in the plaza. It’s a beautiful day, and the outdoor tables of the cafes and tasting rooms are buzzing.

Wine Tasting

Speaking of tasting rooms, we continue our Sonoma wine country weekend with a tasting at Sojourn. One person in our group is a member here, and the winery has a salon just off the plaza.

Sojourn describes itself as a “boutique artisan winery”. It produces highly-rated Pinot Noir and Cabernet Sauvignon wines, among other varieties. We’ve all been fans of their wines for a long time, and we’re excited to be here.

We’re welcomed by friendly hosts who pour us everything from Chardonnay to Pinot and Cab. As we sip, they tell us about the terroir of the vineyards where the grapes are grown. The wines are excellent, and the tasting sets a good tone for what comes next on our itinerary.

Chateau St. Jean

We continue our Sonoma weekend with a trip to Chateau St. Jean. This famous winery in Kenwood is known for both its stunning architecture and its beautiful grounds. With great views of the vineyards, it’s an ideal place to spend a sunny afternoon in wine country.

We’ve reserved a private area at the winery for the next few hours. The space features a lawn with picnic tables and benches, as well as a shaded bocce ball court. As soon as we arrive, our hosts bring out a spread of sandwiches, salads, cheese platters, and champagne.

We settle in for the afternoon, eating lunch and sipping wine before playing games of bocce and Cornhole. The weather is perfect, and the stunning winery building provides a fairy-tale backdrop. It all feels idyllic.

Dinner

From Chateau St. Jean we head back to the Olea Hotel to relax and change for dinner. A few people hit the hot tub, others go for a walk, and still more make use of the outdoor seating areas on the property.

When it comes time for dinner, we hop into pre-booked Ubers for the 5-minute drive to Benziger Family Winery. This famous place has a wine cave that’s ripe for a big dinner, and that’s just what we plan to use it for.

One member of our group got a 20-person dinner here at an auction last fall, and we’ve all been invited to attend. We start with drinks and canapes outside the cellar, soaking up the late afternoon sun as it drifts through the oak trees above us.

As the sun goes down, we head into the cellar for a 4-course meal. The round vaulted room is the perfect place to enjoy dinner in wine country, and we spend the next two hours eating and drinking in good company.

Bar in Glen Ellen

After dinner we’re picked up and driven down the hill into the town of Glen Ellen. The Saloon at The Jack London Lodge is a historic watering hole with lots of atmosphere, and we head inside to continue our night with cocktails.

With brick walls and stained-glass lamps, this place is dripping with heritage and charm. There are photographs and memorabilia everywhere, and lots of locals enjoying drinks. It’s a great place to continue our Saturday night in Sonoma Valley.

Later we head back to the Olea Hotel and make use of the hot tub before turning in for the night. It’s a fun way to cap off a great day in wine country.

Sunday

The next morning our weekend trip continues with another exciting day of discovering Sonoma Valley. We start by checking out of the hotel and making the 10-minute drive to Kenwood.

Brunch

We kick off our day with brunch at a restaurant called Salt & Stone. This place serves California wine country cuisine in a relaxed setting, and it has great outdoor dining areas.

Upon arrival, we’re seated at a long table in the dining room. The brunch menu features everything from huevos rancheros to French toast and chicken and waffles. Espresso drinks and mimosas are welcome sustenance after a big night out, and soon we’re all having a good time.

Later the table fills with food, and we find ourselves tucking into a feast. Our server is animated and entertaining, and we have fun reminiscing about the night before as we fuel up for the day ahead.

Wine Tasting

After brunch we say good-bye to most of the group, then head out for more adventures with the remaining members. We’re off to do some wine tasting, and we head up into the Moon Mountain American Viticultural Area (AVA), one of the few AVAs in the Mayacamas Mountains.

We’ve pre-booked a unique tasting experience at Repris, one of a small number of wineries in this part of Sonoma County. We’re welcomed by friendly hosts who start our tasting with a sample of sparkling wine. It’s a great greeting, and it sets a good tone for the experience.

From there we board ATVs for a tour of the property. Our hosts drive us up into the vineyards and stop at a vista point overlooking the hills. We’re so high up we can see the peak of Mount Diablo from here. Closer in, we enjoy views of the vines as we learn about the volcanic soil on Moon Mountain.

After the ATV tour we take a walk through the winemaking facilities and caves. As we go, we learn more about the history of the winery and the winemaking techniques used here. We’re impressed by what we hear, not to mention how big the place is.

At the end we settle in at an outdoor table and taste everything from Merlot to Cabernet Franc and Cabernet Sauvignon. We like all the wines, and we buy a number of bottles to take with us when we go.

Lunch in Sonoma

Leaving Moon Mountain, we drive into the town of Sonoma for lunch. We’re eating at a local place called HopMonk Tavern, a restaurant near the plaza with a big outdoor seating area.

Situated in a former 1888 farmhouse, this place has loads of rustic charm. When we arrive we’re shown to a table on the deck with great views of the beer garden below.

Soon we’re tucking into wings, smash burgers, and salads as we talk about our favorite parts of the weekend. We’ve done and experienced so many great things that it’s hard to pick a highlight.

Weekend in Sonoma Valley

After lunch we drive back to San Francisco. We’ve had an amazing weekend in Sonoma County, and we’re already talking about our next trip to wine country. I hope my blog post has inspired you to travel to this part of Northern California, too.

If you want more inspiration, you can take a look at my blog post with all my Sonoma itineraries. It has everything from day trips to multi-day adventures and getaways that combine Sonoma and Napa. Whatever you’re looking for, it will help you plan a fun trip of your own.

Itinerary Map

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