Holiday in Healdsburg: The quintessential guide to the Northern California gem

Holiday in Healdsburg: The quintessential guide to the Northern California gem

By Alison Bailin Batz

With world-class dining, wineries and places to rest one’s head, Healdsburg is darn near heaven on Earth. But with hundreds of options – many within walking distance of each other – how is one supposed to even start planning a trip?

Let us do it!


The Grape Leaf Inn, just off the main drag in the heart of Healdsburg and walking distance to nearly a dozen wineries, award-winning restaurants and other attractions, is not only charming, but sneaky cool. In addition to rooms and suites – including a guest house off the main property with its own patio and indoor/outdoor shower – the inn boasts a speakeasy for guests, which is accessible through a secret door hidden behind a bookcase! And while the nearby restaurants are delicious, do not miss Grape Leaf for breakfast. Their lauded chef makes everything from scratch daily and even visits your table to personally help you choose you own culinary adventure.


Cast Wines is a newer vineyard and tasting room to the area, but it cast its spell on visitors and locals quickly (so it is clearly named well!). A chief reason: Its terrace boasts one of the most expansive views of the region, or of any wine region in the country. They also have a festive atmosphere with champagne sabering on the patio and lively Pétanque games (a cousin of bocce) on a custom-built court. Of course, their wine is also exceptional, especially their takes on Sauvignon Blanc and Old Vine Zinfandel. Opt for a seated tasting or a full vineyard walking tour to get the full experience.

Mazzocco Winery has similarly mind-blowing Zinfandel, and a garden patio perfect for spring and summer tastings. A member of the Wilson family of wineries in the region, another option is to book their VIP tour, where you’re whisked away to four of their wineries over the course of six hours with full transportation and an expert guide.

Now, if you can’t make it a full day, definitely visit Mazzocco’s sister winery, Wilson Winery, if you can. Not only is it run by a female winemaker, but it is an area landmark, and not only for its wine and historic barn building. On the lawn, you would be hard-pressed to miss the 26-foot-tall steel coyote, which the owners bought from an artist who had it on display at Burning Man. And yes, you can climb it for the photo opp of a lifetime.

For those seeking photo opps with both feet still safely on the ground, head over to Dry Creek Vineyard, a family-owned vineyard founded by California wine pioneer David Stare known as the birthplace of Fume Blanc. They offer wine blending classes by reservation, where guests can not only taste wine, but blend their own bottle of custom wine as well.

ZO Wines, like Dry Creek, offers tastings. And like Dry Creek, they also offer something extra special: a tasting wheel! Rather than simply savor a flight of wines, your wine guide will take you on an adventure in tasting using a ZO colorful tasting wheel, where you are able to use your own senses to determine the flavors you personally taste in each glass (not what sometime tells you that you should taste). The interactive experience makes novices wine lovers feel comfortable, and it challenges veteran tasters to come up with new ways to describe each sip, smell and swirl in each glass.

And then there is Ferrari-Carano. Yes, that Ferrari-Carano, which owns 1,600 total acres of vineyards across 24 ranches. Most people don’t realize the wine giant, which was founded by a husband-and-wife team of Italian descent, is located in the heart of Healdsburg. The estate is something out of a movie, complete with overflowing gardens, a full Tuscan villa, fountains, statues and tasting experiences for the ages. Certainly, their terrace tasting is special, but if available, splurge on the private wine tasting in their Prevail Room, deep in the heart of their winemaking facility in a VIP room fit for a king.


Beyond being known for its wine, Healdsburg is one of the true birthplaces of the farm-to-table movement, and nearly every restaurant in the area puts the concept into action is some delicious way.

This is perhaps no more evident than at Zazu Kitchen + Farm, which grows almost all of its own produce onsite and at its sister farm down the street. As such, menus change not only with the seasons, but with the daily fresh harvest. Its chef and co-owner Duskie Estes gained national acclaim when she competed on “The Next Iron Chef” on the Food Network in recent years. She has since appeared on the channel several more times, on various programs. Insider tip: order anything on her menu with bacon, including the bacon-infused cocktail.

For a far different experience, but something otherworldly while in Healdsburg, also try Bravas, a tapas bar where it is almost impossible to stop ordering small bites. Hailed by Travel + Leisure as “one of the top 20 tapas restaurants in the U.S.,” Bravas serves up traditional Spanish and modern tapas-style dining in Wine Country by James Beard nominees Mark and Terri Stark.

And then there is Valette. Over a glass of wine nearly two decades ago, two brothers dreamt of a restaurant that would provide a canvas for Sonoma County farmers, winemakers and artisans to showcase their crafts. The restaurant is in Downtown Healdsburg, the heart of Sonoma County and the location where their great-grandfather operated bakeries. They opened Valette in 2015, realizing their dream.

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