Where to Eat, Drink and Stay in Healdsburg, According to Sonoma Valley Locals

• By WineBottleMag
• July 12, 2025
• Drink Eat Healdsburg Locals Sonoma Stay Valley
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To properly explore Sonoma wine country, Healdsburg makes the perfect home base. The charming, historic town sits at the intersection of three different AVAs—Alexander Valley, Dry Creek Valley and Russian River Valley—making it a convenient spot for visiting the region’s best wineries and vineyards. Even better, the downtown is walkable and packed with lively tasting rooms and restaurants, from casual brunch spots to one of best fine-dining restaurants in the world. 

With the Russian River flowing through the western part of town, offering paddling adventures and a scenic backdrop for plenty of bikeable roads and trails, travelers can easily explore the outdoors in between wine tastings and meals. Here’s an itinerary for experiencing the very best of Healdsburg in 36 hours. 

Itinerary

Friday

3 p.m. Settle into town with wine tastings around the square

Healdsburg Plaza is the vibrant heart of the town, but most importantly, it is surrounded by numerous wine tasting rooms. Laurel Livezey, head sommelier at Little Saint, recommends starting at LIOCO, which focuses on bright, minimal-intervention wines from cool-climate sites in Sonoma and Mendocino. “Their Chardonnay is always a standout for me,” says Livezey. For more excellent cool-climate wines, drop in to Ernest Vineyards’ tasting room for wines grown on the Sonoma Coast.

On his rare days off, SingleThread owner-chef Kyle Connaughton likes to stop in at Marine Layer. He says the winery brings “such a thoughtful approach to wine in a relaxed and welcoming space.” Less than a mile away from the square is Bacchus Landing, home to several other wine tasting rooms, including Dot Wine, which focuses on producing Russian River Valley Pinot Noir.

8 p.m. Splurge on a tasting menu

For those with money to spare (and a willingness to snag a competitive reservation), dinner at the acclaimed SingleThread is certainly worth planning an entire trip around. As an alternative, though, Troubadour’s seven-course tasting menu is more accessible in terms of price and reservation availability. Opened by husband-and-wife team Melissa Yanc and Sean McGaughey who both previously worked at SingleThread, Troubadour serves a French-inflected menu using Sonoma produce.

Saturday

8 a.m. Treat yourself to a pastry-filled breakfast

One of the most beloved bakeries in the country, Quail & Condor was started by the same husband-and-wife team that runs Troubadour. The avocado toast and lox on toast are served on the bakery’s famous sourdough bread, and there are plenty of croissants and pastries for the sweet-toothed. 

9 a.m. Browse the farmers’ market

As you walk back from breakfast, stroll through the Saturday morning Healdsburg Farmers’ Market. Sonoma County’s abundant agriculture goes well beyond vineyards, and the farmers’ market is a good place to take in all the wonderful foods the area has to offer. “It’s small, but packed with beautiful produce, flowers and artisan goods,” says Livezey.

10:30 a.m. Kayak or canoe the Russian River

According to both Circe Sher, co-founder of Piazza Hospitality, and Laurel Livezey, there’s nothing like a float down the Russian River on a kayak or canoe in between meals and wine tastings. “It’s so close to Healdsburg but feels peaceful and remote,” says Sher. “The birds, river otters and turtles abound.” There are a few local operators that offer self-guided trips down the river, including Russian River Adventures and River’s Edge Kayak and Canoe.

1 p.m. Find lunch in downtown Healdsburg

There are numerous options for lunch downtown to suit every mood. For a lighter plant-based brunch with a side of wine, Alison Smith-Story of Smith Story Wine Cellars loves Little Saint for its “vibe and very cool chilled wine selection,” especially during the day. Bravas Bar de Tapas is a long-time Healdsburg favorite, serving tapas and sangrias since 2012. Troubadour’s sandwiches are great for a quick and casual lunch.

2 p.m. Head to Dry Creek or Alexander Valley for tastings

Healdsburg is perfectly situated just south of both Dry Creek Valley AVA and Alexander Valley AVA. Reeve Wines up in Dry Creek Valley is a favorite of Connaughton, who recommends the winery for “its laid-back vibe, beautifully expressive wines and seasonal pies from their wood-fired pizza oven.”

If you’re heading over to Alexander Valley and looking for afternoon snacks, Jordan Winery offers tastings of its Cabernet Sauvignon and Chardonnay in a hidden room, paired with bites from chef Jesse Mallgren (who previously ran the kitchen at The Madrona and earned a Michelin star during his tenure). 

8 p.m. Unwind over dinner and cocktails at Lo & Behold 

Take a break from wine and head to industry hangout Lo & Behold Bar + Kitchen for some eclectic comfort food and creative cocktails. Both the food and drink menus change seasonally, but you can always order the restaurant’s fan-favorite dish: housemade kimchi noodles.

10 p.m. Optional nightcap at a local bar

The wine tasting rooms in Healdsburg may not stay open late, but some of the wine bars sure do. If you’re still up for another glass, Smith-Story recommends Maison Healdsburg, which keeps pouring until 1 a.m. “Maison’s Italian offerings are specifically full of treasures among the greats from California and Europe,” says Smith-Story. 

Sunday

9 a.m. Grab breakfast at Acorn Cafe

If you did have a nightcap the night before, then you may want a heartier breakfast at Acorn Cafe, an all-day café with a penchant for breakfast foods. The huevos ranchero or breakfast sandwich here would do just the trick.

11 a.m. Taste Bordeaux-style wines and take in views

If you’re heading south towards Santa Rosa or San Francisco airports, stop at the stunningly scenic Aperture Cellars for a break from the cool-climate Pinot and venture into Bordeaux-style wines. “Aperture offers an inspiring intersection of architecture, art and exceptional winemaking,” says Connaughton. 

1 p.m. Sip bubbles over lunch

J Vineyards & Winery focuses on producing traditional method sparkling wines and they’re best enjoyed as part of the five-course pairing at the winery’s Bubble Room. Estate chef Forest Kellogg sources his ingredients locally and changes the menu every six to eight weeks.

Where to Stay

Bunking in downtown Healdsburg offers the easiest access to tasting rooms, restaurants and boutique shops. Piazza Hospitality operates three minimalist, art-focused hotels that are all a short walk to each other and to downtown.

Hotel Healdsburg is the traditional luxury hotel, with a serene, farm-inspired spa and three elevated dining outlets (including Charlie Palmer’s Dry Creek Kitchen). The eco-friendly H2 Hotel caters to a younger crowd, with more eclectic design and a solar-heated creekside pool. The newest addition, Harmon Guest House, offers a cozier, more residential feel. 

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For a more maximalist stay, there’s The Madrona, one of the best hotels in Sonoma. Set in a 19th-century Victorian mansion, the design-forward hotel’s 24 guest rooms are all distinctly decorated, and the property features artwork curated by Dolby Chadwick Gallery.

Key Wineries

Reeve Wines: Husband-and-wife-run winery notable for its Rieslings and Pinot Noir, as well as a scenic tasting room surrounded by oak trees.

LIOCO: Minimal-intervention winery focusing on Pinot Noir and Chardonnay with a bright tasting room right off of the Plaza.

Aperture Cellars: Small-batch producer of Bordeaux-style wines with a sleek tasting room.

Dot Wine: Small, family-owned winery where Lise Asimont, Foley Family Farms’ viticulturist, strives to make her own perfect Russian River Valley Pinot Noir.

Ernest Vineyards: Female-owned winery producing low-intervention wines from West Sonoma Coast and Mendocino.

Marine Layer: Cool-climate Pinot Noir and Chardonnay from Sonoma Coast with a tasting room in downtown Healdsburg.

J Vineyards & Winery: Sparkling wine producer with a cheese or a five-course lunch pairing menu.

Jordan Winery: French château-inspired estate producing only Cabernet Sauvignon and Chardonnay, offering tasting paired with elevated small bites.

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Where to Eat

Acorn Cafe: All-day café known for its breakfast and brunch items like lemon ricotta hotcakes.

Bravas Bar de Tapas: 13-year-old restaurant offering traditional and modern tapas.

SingleThread: Three Michelin-starred restaurant serving a ten-course, kaiseki-inspired menu.

Troubadour: Intimate sister eatery of Quail & Condor that offers sandwiches with fresh-baked bread during the day. In the evening, it turns into a bistro with a seasonal seven-course tasting menu. 

Little Saint: Artsy plant-based spot known for coffee and ice cream during the day. At night, it doubles as a wine lounge and cocktail bar. Food is served all day and sourced from their own eight-acre farm. 

Lo & Behold Bar & Kitchen: Buzzing local hangout serving shareable comfort food and craft cocktails.

Quail & Condor: Small bakery kneading sourdough bread and croissants, plus avocado and lox toasts on sourdough.

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