How to Spend a Perfect Weekend in Healdsburg, the Under-The-Radar Wine Country Town

Plenty of Michelin stars and a fraction of the headache

May 19, 2023 7:25 am
view of a balcony in a hotel room
For a quieter trip and wine tasting up North, head to Healdsburg.
Christian Horan Photography

When Napa feels too crowded (or too expensive) and you’ve already experienced the best of Sonoma (as in, The Lodge’s oversized outdoor soaking tubs), then it’s time to head to a quieter, more unassuming bit of the county. That would be Healdsburg, my current pick for the best place to go wine tasting up north if you’re not quite ready to shell out on an ultra-private, five-suite hotel.

Healdsburg is the funkier, under-the-radar option for a wine tasting getaway, that still delivers the Sonoma goods. There’s a totally central, totally walkable town, complete with Michelin-star restaurants, numerous tasting rooms and lots of other fun activities — including bike tours, vineyard lunches and art galleries that also make their own vino. Check out some ideas for a weekend itinerary for this extremely cool, still emerging Sonoma County city.

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Getting to Healdsburg

If you live in the Bay Area, just drive. Once you cross the bridge, you can take the 101 North all the way there, and it’s not a trek on meandering back country highways like the drive to Napa. It shouldn’t take much more than an hour unless you’re leaving during peak traffic time. For those flying into the area, stick with the Santa Rosa airport for an extremely easy in-and-out experience in a makeshift terminal. STS might not be the prettiest or most technologically aggressive place, but it’s less than 15 minutes from this airstrip to Healdsburg proper, so there’s really no better way to get here.

Where to Stay in Healdsburg

The best game in town is the Harmon Guest House, a modernist getaway just a few blocks from the main square that nails Wine Country chic with light wood, a fabulous rooftop restaurant and massive suites that will make you feel like royalty while you’re in town. Book into the Founder’s Suite for a two-room setup that includes a full living room, a kitchenette, a powder room, a bedroom with a king bed, soaking tub, separate glassed-in shower and large wardrobes flanking the bed. It also boasts a private balcony that opens into some nearby trees and overlooks the pool.

outdoor terrace with aesthetic sitting areas and rooftop view
Want to stay in a a faithfully restored vintage mansion? Check out The Madrona.
Madrona / © Matthew Millman

We’ve already extolled the virtues of The Madrona, a faithfully restored vintage mansion from the 1880s that puts the luxe in luxury hotel. This boutique property is just a few miles outside of town — less centrally located, but still a great option if you can justify the splurge. Another wonderful place to spend a few days is at one of the 130 bungalow-style guest rooms and suites at the Montage Healdsburg. What’s better than 250+ acres of vineyards and oak groves? Like any Montage, the service is on point, and three separate on-site restaurants mean you technically don’t have to leave. 

outdoor pool with wide seating area and nice sunset behind it
The Montage Healdsburg has 250+ acres of vineyards and oak groves.
Montage / Christian Horan Photography

For those who do want the town experience, one more in-the-mix spot is Hotel Les Mars, another guesthouse that’s right off the main Healdsburg town square. This French chateau-style hotel is part of the renowned Relais & Chateaux group. The 17th- and 18th-century antiques and the Old World furnishings used throughout the property make this a particularly romantic choice. 

scenic wooden seating area in a guest house
The Old World furnishings used throughout the Hotel Les Mars make this a particularly romantic choice.
Hotel Les Mars

Where to Eat in Healdsburg

Even if you don’t stay at The Madrona, definitely take the short car ride over to the property to try their terrace restaurant, where fruits and vegetables from the property’s regenerative garden dominate the menu. Along with excellent cocktails, they offer an aged spirits tasting menu for the connoisseur’s palate. 

If staying at Harmon Guest House, make sure you check out The Rooftop. Instead of Michelin vibes, it’s just classic tapas like tacos, sliders and tartare, which can be a nice break from formal prix fixe tasting menus. Get the ricotta donuts with mango marmalade for a surprising sweet treat. Another nearby cafe is Spoonbar, a great place to grab casual breakfast and coffee.

For lunch, check out Healdsburg’s best sushi, Asahi Sushi & Kitchen, with plenty of classics and more playful fare like a sushi burrito, or the Healdsburg roll, which appropriately includes truffle oil. They also serve omakase-style Thursday to Sunday for the more adventurous diner. If you make it known that you’re a sake lover, don’t be surprised if the chef here starts pouring rare gems from his substantial collection. 

One of the Michelin-starred spots in town is ​​Barndiva, a local fixture with a gorgeous backyard patio that dubs their offerings “modern country cuisine.” The prix-fixe dinner menu is offered Wednesday to Sunday with dishes like Persian cucumber salad, potato mille feuille with peas and Mt. Lassen trout. Another high-end dinner spot, ​​The Matheson’s Roof 106, offers views of the square, an extensive local wine list and wood-fired pizza from a specialty Mugnaini oven. Come for golden hour and pair one of the extra-fresh pies, made with 72-hour fermented dough, with a glass from a Healdsburg producer to get the full effect.

Finally, the kitschy Costeaux French Bakery is a local fixture and the perfect place to stop on your way out of town. Grab a loaf of their infamous sourdough cinnamon walnut bread, or sit and have a Monte Cristo sandwich with ham, turkey and Jarlsberg cheese to get a mix of sweet and savory.

What to Do in Healdsburg

wine bottle and wine glasses at a table with food in front of a lake
Take part in Jordan Winery’s outdoor Harvest Lunch.
Jordan Winery

Hands down, the best thing to do in Healdsburg is wine tasting. For a more immersive experience, head to Jordan Winery and take part in their outdoor Harvest Lunch. Each course is paired with a generous pour of Champagne, specialty chardonnay or cabernet sauvignon. These lunches take place during the actual harvest season, in September and October, but other wine and food pairings hosted on their 1,200-acre estate are available to book year-round on their site.

a spread of food on a table
Endulge in a mezze board from Little Saint.

In town, the Marine Layer Wines tasting room is a modern, stylish space on the main square, where their Sonoma Coast chardonnay and pinot noir are poured, with mezze boards from their plant-based neighbor Little Saint. Don’t miss Harris Gallery, as the father-son duo who make most of the art displayed in the space have ventured into wine, too. 

For those who don’t mind a good, solid bike ride — this is absolutely not a vanity mile-long jaunt on a beach cruiser — book a Sip ‘n Cycle tour with Getaway Adventures. As mentioned, you will literally work up a sweat on this substantial 10 to 12 mile ride out into the meandering country roads. You’ll stop at places like the garden tasting area of Dry Creek Winery and sit around the pond at Mill Creek Vineyard, for a full, visceral sense of the surrounding terroir. It’s $250 for a full-day guided tour with two to three wineries (tasting fees not included) and a picnic lunch from Oakville Grocery.


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