Now's the Time to Visit Sonoma County's Most Wine-Friendly Town

Three-bedroom guesthouse
Three-bedroom guesthouse

Photo by Christian Horan

Here's how you get to Healdsburg, California. First, have yourself born into an Italian family near Lucca in the late 1800s. Then, as a young woman, realizing you will never inherit any of your family's land, immigrate to America by yourself at age 19. Arrive in New York, make your way across the country alone by train, and get to San Francisco just after the disastrous earthquake of 1906. There, meet an industrious carpenter (also Italian), marry him, and convince him to move north of the city to a one-dirt-road town called "Healdsburg" to start a winery. At least, if your name is Letizia Rafanelli, that's how you do it.

The rest of us, well, we get on a plane.

A. Rafanelli Vineyards
A. Rafanelli Vineyards

Photo by Kim Carroll

I've been visiting Healdsburg regularly for years. While the town has changed drastically since I first started coming here, A. Rafanelli Vineyards has not changed much at all (though the family did move out to Dry Creek Valley after Prohibition). Its signature Dry Creek Valley Zinfandel is still a benchmark for the variety: a tumble of lightly spiced black cherry and boysenberry flavor, silkily textured, beautifully balanced.

"When they started, in the early 1900s back in town," Rashell (Shelly) Rafanelli says, "my great-grandparents sold their wine by the barrel: California Claret, California Burgundy. Back then the land was all pears and prunes."

READ: The 17 Most Important California Vineyards All Wine Lovers Need to Know

No longer. Dry Creek Valley, sweeping south down to Healdsburg, is row after row after row of vines; 9,000 acres of Zinfandel, Cabernet, Sauvignon Blanc. Hit the town, keep going to Russian River Valley; 15,000 acres of Chardonnay, Pinot Noir, and more Zinfandel. Healdsburg lies on the dividing line. And right now is a particularly exciting time to visit.

Healdsburg hasn't been nearly as gussied up as much of Napa Valley, and though it's the premier destination for Sonoma County wine tourism, it still feels like an actual town. You can get a three-Michelin-star meal at chef Kyle Connaughton's Japanese-influenced SingleThread, but you can also pull in next to the pickup trucks at the Casa del Mole food market and get some really excellent Oaxacan-style tacos for lunch.

READ: Meet the Sauvignon Blanc Savant

There are a number of excellent restaurants here—Barndiva, Spoonbar, Dry Creek Kitchen—but the standout recent opening is unquestionably chef Dustin Valette's The Matheson. Valette, who grew up in Healdsburg, has gained acclaim at his eponymous restaurant right off the town square, but the three-story Matheson is a far more ambitious project. In the soaring space downstairs, Valette's own farm-to-table cooking shares a menu with sashimi, nigiri, and rolls from local sushi star (and friend) Ken Tominaga. Up top, more casual fare such as pizzas and yakitori skewers arrive at tables on the terrace overlooking the town square. And yet, even though The Matheson is entirely new, history plays its role here, too: Valette's grandfather's bakery, Snowflake, was once located in part of the same space. (It closed in the 1950s.)

I capped off a recent visit with a stay at the long-awaited Montage Healdsburg, which opened at the end of 2020 just north of town. Call it Healdsburg's answer to Napa Valley's super-luxe Meadowood resort: Cheerful staff members golf-cart you and your luggage to one of the many light-filled rooms located in luxurious bungalows scattered around the 258-acre property. There is little that beats having your morning coffee on a terrace in an absurdly soft bathrobe with views over the hills of Sonoma, or enjoying chef Jason Pringle's cooking at the property's Hazel Hill restaurant, or lounging outside on a warm September afternoon, Aperol spritz in hand.

I wonder what Letizia Rafanelli would think about how much that little town she landed in way back in 1911 has changed. But since they do have Rafanelli Zinfandel on the list at the Montage, my guess is she'd be just fine with it.

Where to Stay

Montage Healdsburg

Located a few minutes outside Healdsburg, this is easily the most luxurious opening in Sonoma's wine country in years. At its Hazel Hill restaurant, chef de cuisine Jason Pringle has a deft touch; the wine list, overseen by sommelier Petra Polakovicova, offers an abundance of both familiar and lesser-known names. (Rooms from $1,200,

Harmon Guest House

Located immediately off the Healdsburg town square, this 39-room, California-modern getaway has airy rooms with a luxe-casual feel and an excellent rooftop bar—once in a while, after a day or two of wine tasting, a cocktail is just the thing. (Rooms from $389,

Where to Eat

The Matheson

Hometown chef Dustin Valette's magnum opus is this three-story destination on the Healdsburg town square. The downstairs room offers more than 100 wines by the glass and dishes like an heirloom tomato salad with sea beans and whipped burrata; the casual upstairs is a great place to sit and look over the town with a cool glass of Chardonnay. (

Journeyman Meat Co.

If you're planning a picnic, or just need some excellent salumi because you're hungry, this tiny shop is the source. After his family's eponymous winery sold, Pete Seghesio studied the art of curing meat; his Calabrian salami, with Zinfandel and Calabrian chiles, is a standout, as is the "vintner's coppa," made with a proprietary herb-spice mix and sliced to order at the counter.

Quail & Condor

Pastry chef Melissa Yanc started out selling her absurdly good pastries and breads at the Healdsburg farmers market and then opened this small shop in January with money she won on the Food Network's Holiday Baking Championship back in 2019. The pistachio croissant, a thing of beauty, is crazy delicious. Order ahead online, or plan to wait in line. (

Little Saint

This eagerly anticipated new restaurant/wine bar/bottle shop concept from chef Kyle Connaughton and his wife, farmer Katina Connaughton (of the three-Michelin-star SingleThread), is set to open later this year. The menu will be entirely plant-based, focusing on produce from the restaurant's dedicated 24-acre farm nearby, as well as from local producers. (

Where to Drink

Hirsch Vineyards

The Hirsch vineyard is one of California's greatest Pinot Noir vineyards, located miles and miles down winding roads on the far Sonoma Coast. Luckily, their tasting room is situated right on Healdsburg's main square. It's by appointment only on Fridays and Saturdays (tastings are $50 per person) and is worth the effort to taste Hirsch's hard-to-find, single-parcel Pinots. (

Marine Layer

At Marine Layer's gorgeous new tasting room on the square, guests taste cool-climate, single-vineyard Pinot Noirs and Chardonnays from some of the area's best vineyards—Gap's Crown, Heintz, and others. With its coastal-cool vibe and lounge area, it's an ideal spot for relaxing before dinner. (

The Drink

Stop in at this spot near the Russian River, a few blocks off the town square, to taste wines from two great boutique producers. Mike Lucia's Rootdown Wine Cellars makes restrained, cool-climate wines from overlooked varieties like Grenache Blanc, Trousseau, and Mourvèdre; Leo Steen Wines reflects winemaker Leo Hansen's longtime fascination with Chenin Blanc, and his are some of the best in the state. (

Aperture Cellars

A new arrival located about five minutes south of Healdsburg's town square, Aperture is the home of winemaker Jesse Katz, who also farms 15 acres of vineyards on the Montage Healdsburg property. The winery's name is a nod to his father, acclaimed photographer Andy Katz, whose beautiful black-and-white prints adorn the walls at the incredibly striking cellar door. Katz concentrates on Bordeaux varietals—make an appointment in advance for the $50 "Soil Series" tasting to try his focused Sauvignon Blanc and firm, classically styled Cabernet Sauvignon, among others. (

A. Rafanelli Winery

Call directly (707-433-1385; no emails) to taste at this historic winery, located off Dry Creek Road about six miles north of Healdsburg. The complex Zinfandel is a benchmark for the variety, and the Alexander Valley Cabernet, with its blueberry and toasty currant notes, is both complex and ageworthy—the 1995 that I tasted with winemaker Shelly Rafanelli was surprisingly young and thoroughly delicious. (

Ridge Lytton Springs

This iconic producer's Lytton Springs eco-friendly winery is built of straw bales and vineyard clay (though you'd never guess) and largely powered by solar. Spring for the "Century Tour" to take a physical tour of the estate, followed by a liquid tour of several vintages on the outdoor terrace overlooking the 115-year-old vineyard that surrounds the winery. ($50, 11 a.m. and 2 p.m. daily, reservation required;

Bricoleur Vineyards

This new winery estate has some of the most beautiful grounds in the Healdsburg area, plus some of the best food (thanks to acclaimed chef Charlie Palmer, Bricoleur's new culinary adviser). Book a "Sip & Savor" tasting ($85), and try small bites like a chilled English pea soup with pancetta-shallot crumble paired with the winery's 2019 Kick Ranch Sauvignon Blanc. Because each of the six dishes is created to pair with a specific wine, it's a remarkable experience. (