2 Perfect Days (and Nights) in Healdsburg

The charm and genuine down-to-earth personality of Healdsburg is inescapable. From the sounds of jazz and laughter at town square events, to the enticing aromas of five-star cuisine, to the country roads winding through rolling hills of world-acclaimed wine growing appellations, Healdsburg acts like a magnet for wine-loving visitors to Sonoma County.

Take a stroll around town, and you’ll discover the treasures and treats of small town individuality that make Healdsburg so special. World-class shopping. Renowned art and sculpture. Locally grown organic produce and artisanal breads, wines and cheeses. Independent bookstores. Treasure troves of antiquing.

Healdsburg is surrounded by several of Northern California’s finest regional wine appellations, including Alexander Valley, Chalk Hill, Dry Creek Valley and Russian River Valley. Centrally located to more than 100 world-class wineries and tasting rooms, Healdsburg is the ideal place to discover all the best that Sonoma County wine country has to offer.

It’s also a great place to hunker down, park the car, and soak in the local flavor at a leisurely pace. We’ve built this two-day itinerary with that in mind.


Arrive at the airport of your choice in the early or mid-afternoon. Most wine country visitors fly in to San Francisco International Airport, but we suggest opting for either the Oakland or Sacramento airports. You’ll typically encounter much less traffic and get to Healdsburg faster.

Once you get close, follow the signs to the Healdsburg town plaza, and check in at the Hotel Healdsburg – classy, modern and comfortable, with a pool and spa. The nightly room rate includes a hearty breakfast each morning of your stay.

Take some time to unpack and unwind before heading to dinner at the Dry Creek Kitchen. No need to hop in the car; the restaurant is part of the hotel.

If the weather allows, ask for a seat on the arbor-shaded patio, and feast your eyes on the menu that stresses fresh, local ingredients. Start with the salmon carpaccio, just to remind yourself that you are now officially on vacation.

The wine list is just as impressive as the menu, boasting 650 local bottlings. Since you don’t have to drive home, you may as well splurge and order a full bottle to share.


After eating breakfast at the hotel, stroll a block west of the plaza and take in the Healdsburg Farmers Market. And don’t be surprised if you see some of the staffers from the Dry Creek Kitchen there; numerous local chefs base nightly specials on the fresh ingredients they can procure at the market.

After that, walk back to the plaza to explore the array of shops, almost all of which are locally owned and unique to Healdsburg. It’s a great place to shop for gifts, including items you’ll find only in wine country.

When it’s time for a snack, head back to the Farmers Market and pick up a delectable tamale or taco from the Yucatan Tamale Truck. If your sweet tooth is calling, ask a local for directions to the Downtown Bakery & Creamery and order a doughnut muffin. Everyone who lives in Healdsburg knows where the Downtown Bakery is.

Don’t eat too late in the afternoon, however, because tonight you’ll be dining at Cyrus, where you’re likely to be served as many as 17 “small plate” selections that are guaranteed to satisfy the foodie in you. Cyrus is expensive, but worth it.


Begin the final day of your stay with another filling breakfast at the hotel, then pack up, check out, load your car and head to the nearby Seghesio Family Vineyards.

The winery’s “Family Tables” offers the opportunity to sit and relax – away from the busy tasting room bar – to enjoy wine as it was intended to be experienced: around a table with food and friends.

You’ll meet chef Jon Helquist – whose 19 years of culinary experience began at Chez Panisse and included stints at Oliveto, the Martini House and Manzanita – as he prepares and serves recipes showcasing the bounty of Sonoma County.

Located where wine has fermented for more than a century before “gravity flowing” into the cellar below, the “Family Tables” rooms overlook the cellar and feature tables crafted by Ed and David Seghesio from the large redwood tanks once housed at the winery. Talk about an inventive recycling idea.

Weekend seatings begin at 10 a.m., with each day’s final seating at 3:30 p.m. The cost is $35 per person.

Sadly, it’s now time to bid farewell to Healdsburg and return to the airport for your flight home. Don’t be surprised if the primary topic of conversation in the car is how soon you could come back.



29 North St.


Downtown Bakery & Creamery

308 Center St.


Dry Creek Kitchen

317 Healdsburg Ave.


Healdsburg Farmers Market

One block west of Plaza



109-A Plaza St.


Seghesio’s Family Table


Note: The Healdsburg Farmers Market and Seghesio’s Family Table have seasonal hours, so be sure to inquire before panning your trip.

Posted in Our Wine Travel Log
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