Healdsburg has long been a destination for tourists looking to explore the wine regions in the area, but this darling village has undergone a transformation over the past few years. Today, a visit to this picturesque town means access to hip restaurants, cool cafes, and eclectic boutiques. Check out our guide for the ultimate weekend experience.

Where to Stay

Image Source: Yelp

H2 Hotel 219 Healdsburg Avenue Healdsburg, CA 95448 (707) 431-2202 TripAdvisor: 4.5 stars, 405 reviews Eco-friendly H2 Hotel is just a one-minute walk from the plaza. This boutique hotel is charming and LEED-certified, offering 36 modern and sleek rooms with an organic and sustainable design. Insider tip: Plan for at least one meal at the hotel’s restaurant, the chic and sophisticated Spoonbar. Expect elevated takes on rustic cuisine like meyer lemon ricotta gnudi pasta, and herb-roasted black angus tenderloin.

Where to Taste

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J Vineyards 11447 Old Redwood Highway Healdsburg, CA 95448 (888) 594-6326 TripAdvisor: 4.5 stars, 152 reviews Enter J Vineyards by walking under the trellised archway. Then sit back, relax, and enjoy some sparkling wine in the Bubble Room, or head to the terrace to enjoy some Pinot Noir and Vin Gris paired with small bites. The vibe is low-key, yet elegant. Insider tip: To learn about the process of making sparkling wine, sign up for the J Tour and Tasting and take a behind-the-scenes look at the production techniques.

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Cast Wines 8500 Dry Creek Road Geyserville, CA 95441 (707) 431-1225 TripAdvisor: 5 stars, 37 reviews Located in nearby Geyserville, Cast Wines offers a smaller, more intimate experience than many of the neighboring wineries. Tastings are held on the terrace where visitors taste through four of the current releases while enjoying the bucolic scenery. Insider tip: After tasting, head to lunch at Diavola Pizzeria for wood-fired pizza and house-cured salumi.

Where to Dine

Image Source: Flying Goat Coffee, Yelp

Flying Goat Coffee 324 Center Street Healdsburg, CA 95448 (707) 433-9081 TripAdvisor: 4.5 stars, 182 reviews For a quick breakfast or afternoon pick-me-up, grab a cup of coffee and a croissant at bright and airy Flying Goat Coffee just off of Healdsburg Plaza. Insider tip: Non-dairy coffee drinks and gluten-free baked goods are available.

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Chalkboard 29 North Street Healdsburg, CA 95448 (707) 473-8030 TripAdvisor: 4.5 stars, 256 reviews Enjoy seasonal small plates and creative craft cocktails at this hot spot just off Healdsburg Plaza. The cuisine is inventive and the restaurant has a stylish, modern vibe. The pork belly biscuits are always a favorite. Insider tip: Consider indulging in the “candy bar” dessert, a yummy concoction of peanut crunch, brownie, nougat ice cream, and caramel. Or perhaps a maple bacon glazed donut for a combination of salty and sweet.

Image Source: Dry Creek Vineyard, Yelp

Dry Creek Kitchen 317 Healdsburg Avenue Healdsburg, CA 95448 (707) 431-0330 TripAdvisor: 4 stars, 655 reviews Dry Creek Kitchen is Healdsburg’s quintessential Wine Country dining destination. Elevated and elegant, the experience is always the perfect marriage of impeccable service and top-notch new American cuisine crafted by owner and chef Charlie Palmer. Insider tip: For a true night of indulgence, consider the five-course tasting menu.

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SHED 25 North Street Healdsburg, CA 95448 (707) 431-7433 TripAdvisor: 4.5 stars, 181 reviews SHED is a modern and stylish destination for shopping and dining, attracting foodies, coffee addicts, and gardeners alike: the intersection of Healdsburg’s rural and and urban offerings. Schedule enough time to peruse the cool mix of products and great food in this hip, airy space, and stay for lunch at the cafe and sit outside among the growing greens featured on the menu. Insider tip: Check out the interesting housemade ice cream flavors, like carrot turmeric.

Things to Do

Image Source: River’s Edge Kayak and Canoe Trips, Yelp

River’s Edge Kayak and Canoe Trips 13840 Healdsburg Avenue Healdsburg, CA 95448 (707) 433-7247 TripAdvisor: 4.5 stars, 34 reviews Take in the serene beauty of the Russian River with a kayaking trip from River’s Edge. Expect lots of wildlife sightings and plenty of beaches to bank at along the way. Insider tip: After an afternoon of adventure, head to Bear Republic Brewery for a flight of beer and brewpub fare.

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Studio Bel Vetro 1441 Grove Street Healdsburg, CA 95448 (617) 686-4194 Contemporary art lovers and designers will love Studio Bel Vetro’s showroom, where artisan glass and lighting fixtures are on display. Everything is handmade, including custom, expertly crafted light fixtures ranging from table lamps to authentically designed Venetian-style Reticello decorative chandeliers. Insider tip: If you’re in the market for a one-of-a-kind piece, talk to the designers about a custom order.

Image Source: Punch Clothing, Yelp, Facebook

Punch Clothing 711 4th Street Santa Rosa, CA 95404 (707) 526-4766 Boutique Punch Clothing specializes in current women’s fashion trends in designer clothing and accessories. The focus is on quality, well-made goods like leather goods and cotton, all made in the USA. Insider tip: Costeaux French Bakery is just a block away. Head north to stop by for some French-style pastries after shopping. It’s not likely you can get your fill with just one visit to picturesque Healdsburg. Try to take in as much of the scenery, cuisine, and wine tasting as this visit permits, then start planning to come back soon. There’s plenty to do in this idyllic, Wine Country town.

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Author

WineCountry Collective

WineCountry is made up of a dedicated and passionate team of wine, food, and travel aficionados. We diligently explore regions, both near and far, to curate the best ideas and resources. Whether you're musing over your next wine escapade, planning a romantic weekend away, embracing the Wine Country lifestyle at home, or are simply looking to be entertained for a moment, trust us to be your comprehensive guide.