Discover this quintessential wine country destination.
By Steve Zepezauer
Healdsburg, which is quickly becoming the go-to destination in Sonoma’s wine country, exhibits a seamless balance of small-town charm and sophisticated taste. Surrounded by more than 60 wineries, the welcoming downtown features tasting rooms from world-class wineries and a thriving culinary scene.
Located just 15 minutes from Charles M. Schulz-Sonoma County Airport, an easy flight from Orange County, or a 90-minute drive from San Francisco, Healdsburg is a perfect destination for a long weekend. The following 48-hour itinerary provides a sample launching point to discover a taste of this quintessential wine country town.
Where to Stay
From hip and sophisticated like Hotel Healdsburg to quiet and enchanting like the Cottages at Healdsburg, there are multiple appealing options to stay in the quaint downtown area. Hotel Healdsburg, located on the western edge of the town square, exhibits modern wine country ambiance combined with urban sophistication. With minimalist aesthetic and maximalist perks like free valet parking, free breakfast and complimentary wine tastings from local wineries (from 3-5 p.m. Thursday through Saturday in the lobby), this property features the upscale Dry Creek Kitchen restaurant by acclaimed chef Charlie Palmer, a gourmet pizzeria and a full-service spa featuring biodynamic treatments and locally sourced products. It all sounds very luxurious, but feels more like Healdsburg cool.
For a more secluded experience, the Cottages at Healdsburg are a hidden gem. Although just a block away from the center of town, the four farm-style cottages are in a very private residential setting. Surrounded by mature cypress and olive trees, the old-fashioned yet modern cottages are the epitome of cozy. Each cottage features a private entrance, master suite with California king bed, en suite bathroom, fireplace and fully stocked kitchenette. Enjoy your morning coffee on your private deck before you start your day and end the evening with a bottle of wine from a local winery on the same spot.
Day One
Morning
Begin your morning with a stroll around the historic Healdsburg Plaza. The 1-acre park in the center of town is a focal point for everything cultural nearby from dining, tasting rooms and shopping. After getting your bearings, head to Costeaux French Bakery. This family-owned local favorite has been serving up French cafe classics like quiche, croissants and freshly baked bread to Healdsburg patrons since 1923. An ideal place for breakfast or brunch, you can also order a boxed lunch to take with you on your wine country adventures. Or head to another local staple, the Flakey Cream. This mom-and-pop-style breakfast and doughnut shop is known for its laid-back atmosphere and high-quality ingredients. Try one of the seven signature egg Benedicts and fuel up at the espresso bar before heading out for the day.
Afternoon
After breakfast, a must-do on your first day is the Healdsburg Wine and Food Pairing Walking Tour. Beginning in the plaza, this four-hour outing (which sounds like a lot, but you’ll wish it was longer), curated by Wine Country Walking Tours, is more of a wine education and foodie experience with bits of history on the town thrown in for good measure. You’ll get to have engaging experiences at three different tasting rooms/wineries plus one hidden gem, all within short walks of each other in the downtown proper. The tastings are thoughtfully paired with savory bites created with local ingredients from Sonoma County farmers and purveyors.
A few of the local tasting rooms often included on the tour are Stephen & Walker Winery, an artisanal winery led by the legendary winemaker Nancy Walker that creates amazing wines sourced from select vineyards in Sonoma, Napa, Mendocino and Monterey counties; Rockpile Vineyards, producers of elegant and complex red varietals including zinfandel, petite sirah, cabernet franc, syrah and cabernet sauvignon; and Roadhouse Winery, which specializes in handcrafted pinot noir. Each unique tasting room offers a memorable experience and excellent wines.
In addition to the wine pairings, you will be treated to an additional Healdsburg gem such as Russian River Tea Co., which carries a wide assortment of proprietary tea blends to impress any tea aficionado as well as a full offering of handcrafted chocolates.
Evening
After a late afternoon wine nap, get ready for a unique and creative meal at the plant-based restaurant Little Saint. The much-talked-about destination venue was named to The New York Times’ “Best 50 restaurants” list in 2022 and recently reopened under new ownership. Much more than a restaurant, the very communal setting at Little Saint also includes a coffee bar, wine lounge, cocktail bar and music venue. Or head to The Matheson, the popular tri-level modern concept that features a main restaurant, two bars, a wine wall featuring 88 wines on tap and a super cool rooftop lounge, known as Roof 106, perched above Healdsburg Plaza. The emphasis is on local and micro-seasonal ingredients: Roof 106 focuses on dishes created from a wood-fired oven, including multiple pizza options, while the main dining room, The Matheson, is more formal and geared toward modern wine country cuisine.
Day Two
Morning
Take a short walk over to Black Oak Coffee Roasters. In a town full of hip places, this place is another standout. Already a legend in the town of Ukiah (about an hour’s drive from Healdsburg), Black Oak has quickly become a local favorite here as well since opening in 2021. Not only do they serve award-winning coffees in a quaint, historic building, the cafe serves up several satisfying breakfast options that you can pair with drinks from the two-time winner of North America’s largest coffee roasting competition; the business also snagged the prize for America’s Best Espresso in 2017.
Afternoon
Now that you’re fueled up, visit one of the many local wineries. A great one to experience is Alexander Valley Vineyards, which is a beautiful 15-minute drive from downtown. Reserve a spot on the Vineyard Hike ($60). This grape-to-glass tour takes you on an easy guided hike through the Wetzel Family Estate where you’ll learn about some of the brand’s iconic wines and get to taste them where they grow. The experience includes a boxed lunch on the porch of the tasting room where you can continue to take in the magnificent views.
When you get back to town, hop on a bike and explore the outskirts of downtown (bikes are complimentary for guests at Hotel Healdsburg). There’s the popular Healdsburg Loop trip that’s a very scenic 12 miles through the vineyards of Dry Creek Valley. Or if you’re ready to swap out grapes for grain, take a shorter ride out to the Fogbelt Brewing Co. and check out the beer garden next door to the historic train station.
Evening
Take another walk around Healdsburg Plaza on your way to the Marine Layer Wines tasting room for a pre-dinner tasting. Marine Layer, which is known for its Sonoma Coast-focused, small-batch wines, recently opened this coastal chic tasting room downtown. Try the Marine Layer Flight to sample five limited production wines and add on a mezze plate prepared by Little Saint restaurant.
When you’re ready for dinner, take the pleasant stroll over to the h2hotel. This contemporary, eco-friendly gem is home to Spoonbar, which focuses on local California cuisine. After taking selfies in front of the mesmerizing “Spoonfall” water sculpture near the entrance to the hotel, opt for a table on the back-garden patio. Enjoy the ambiance while sipping a creative cocktail from the eatery’s extensive offerings and inspired comfort food from the seasonal menu.
If You Have More Time…
There is so much more to explore in the area so, if you have the time, visit one of the newest additions to the area, the Montage Healdsburg. Nestled among 258 acres of vineyards and oak groves, this truly unique property is worth seeing. Have lunch or dinner at Hazel Hill while gazing out at the vines. For beer lovers, a go-to destination is the Russian River Brewing Co. This second location in Windsor (the original location is in Santa Rosa) includes a beer garden and a pub. Pop in for a couple pints of the legendary Pliny the Elder (named best beer in America several times over).
