California Itinerary: Head to Healdsburg While It's More Martha Than Wintour

Napa's little sister isn't jokingly known to insiders as "Beverly Healdsburg" for nothing. Just 69 miles north of San Francisco via the 101 will land you in the brightest little star of Sonoma County. Equal parts rustic and chic, the town of Healdsburg has risen quickly, despite the looming shadow of its highly publicized older sibling, Napa Valley. 

But like most-younger children, Healdsburg is scrappier and savvier; with less to prove and more to gain. Brimming with fabulous restaurants, biodynamic vineyards, and a town square like Mayberry; it’s not hard to find the appeal. Our short-list hits all the high marks with plenty left to be discovered. Our advice? Go now, while she’s a little more Martha and a little less Wintour.

Here is our play-by-play for a full weekend itinerary in Healdsburg:


10AM: Healdsburg Shed

In their effort to connect the dots between the much over-used phrase: “farm to table”, the Healdsburg Shed houses a market, café, and large gathering space under one, stylish roof. Set against a sea of white, the indoor-outdoor space encapsulates California living. After a simple, delicious breakfast (we love the toasts and the cappuccinos), browse  the mini-market, stocked with an assortment of goodies that range from local honeycomb to a picnic basket.

1PM: Quivira Vineyards & Winery

A trip to Healdsburg is never complete without a stop by one of our favorite vineyards, which also houses one of the dreamiest, most comprehensive organic and biodynamic gardens we’ve ever seen.  Over 120 raised beds dot the property, amongst a small pond, bee hives, and a chicken coop.  If given the opportunity, bike there.  West Dry Creek Road angles through many lovely vineyards, and Quivira offers a welcome reward about 6 miles outside of town.

4PM: Healdsburg Modern Cottages

For a boutique experience, check into one of these four small cottages built in the 30s, but upgraded with inspired, modern finishes (think: Eames). If you crave privacy, accessibility, and comfort, Healdsburg Modern Cottages will provide just that.  All of the recreational essentials included: bicycles to tot around town, and a small private pool for relief from the hot, afternoon sun.  

7PM: Spoonbar

After a day of wine tasting, you might find yourself craving a flavor break. Enter: Spoonbar. Pull a seat up against the bar and consult with some of the finest mixologists in town. Cocktails are prepared with precision, fine ingredients, and with a flair for accoutrement. The expansive menu runs the gamut from a classic Pisco Sour to a Carbonated Raspberry Collins (on tap, no less). 


9AM: Downtown Bakery

We like our coffee, but we love our pastries, and no one does it better than Downtown Bakery. It’s no frills, in the best way possible. Located conveniently off the town square, your eyes will widen with joy at the sight of house-made sticky buns, sugared donut-muffins, and fresh-fruit galettes. You might want to grab a pastry here then head down the block for your coffee at Flying Goat, but that just depends on how your morning is going.

1PM: Oakville Grocery

Rise and shine, rested; and get right into wine tasting.  Most tasting rooms open at 11AM.  For all-day sustenance while on the road, make a pit stop at Oakville Grocery. Cars line the highway and picnic tables provide ample space to tie up your pup (if you brought them) and relax under the shade trees. It’s a market with amazing made-to-order sandwiches; whether it’s braised pork on brioche or Petaluma chicken salad with apple-fennel slaw, they’ve got you covered.

2PM: Preston Farm & Winery 

Another all-time favorite, Preston is a biodynamic, family-run farm with love and authenticity seeping from every corner.  From the spotted piglets rummaging through the vines, to the rusty buckets of bocce balls plopped alongside the court; not only do they create a superb selection of wines (the Sauvignon Blanc is a personal fave), but if you’re lucky, you might snag a bottle of their coveted (and limited) olive oil harvest.  If available, they generously serve tastings alongside a warm country loaf.

7PM: Diavola Pizzeria

Sneaking onto our list is Diavola Pizzeria, in neighboring township, Geyserville. Although it’s not technically located in Healdsburg, it’s worth the short drive north. California meets Italy with house-cured meats and inspired greens. It’s a local favorite, so expect a crowd and enjoy a glass of red while you wait on the front porch that's straight out of an old Western flick.

More Northern California on Salt & Wind

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Opening photo by Trinette Reed