Visit 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 Healdsburg, California — 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. 

Why Visit Healdsburg California?

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 that looks like Mayberry, it’s not hard to find the appeal.

Our shortlist 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.

Healdsburg California Weekend Itinerary

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

Day 1

10 AM: Quail & Condor

Set just south of the town square along the main street, you could drive past and miss the quaint local bakery but make sure you don’t! Head there just before opening when the baked goods are freshest and join the queue of in-the-know locals and cyclists. After picking a treat (we love the granola and all the pastries) make sure to get a coffee to go.

1 PM: 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, beehives, 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.

4 PM: Healdsburg Modern Cottages

Though you can stay at luxury properties like the Hotel Les Mars or the Montage Healdsburg, we like to go hyperlocal. 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 recreational essentials included: bicycles to tot around town and a small private pool for relief from the hot afternoon sun.  

7 PM: 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 a flair for accouterment. The expansive menu runs from a classic Pisco Sour to a Carbonated Raspberry Collins (on tap, no less). 

DAY 2

9 AM: Downtown Bakery

We like our coffee, but we love our pastries, and few do 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 and then head down the block for your coffee at Flying Goat, but that depends on how your morning is going.

1 PM: Oakville Grocery

Rise and shine rested and get right into wine tasting as most tasting rooms open at 11 AM. 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. Its market has 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.

2 PM: 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.

7 PM: Diavola Pizzeria

Sneaking onto our list is Diavola Pizzeria, in the 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.

Planning A Trip To Healdsburg California

At Salt & Wind Travel, we’re here to help lovers of food and wine travel to the top wine regions. Our travel planning services are ideal if you want to see the real destinations when you arrive rather than just landing in another tourist trap, if you don’t have the time to plan your trip, or if you’re unfamiliar with your planned destination.

Let us help you plan your California wine region’s vacation so that you can have the trip of a lifetime. You can learn more about our California travel planning services here.

Photo Credit: Opening photo by Trinette Reed