Die-hard Sonoma wine country fans have witnessed the sleepy, two-street town of Healdsburg blossom into an upscale destination, complete with world-class accommodations, tasting rooms, fine dining and craft cocktails.

Here is my intimate, personal guide to spending a memorable weekend, filled with wonderful wine, fabulous food and rousing romance in the quaint town of Healdsburg.

Should you crave European-style decadence and impeccable service, Hotel Les Mars, a Relais and Chateaux designated property, is well worth a splurge. However, if you prefer a contemporary, eco-friendly hotel, featuring casual yet chic and comfortable accommodations, H2 Hotel may be your perfect spot. Plus – a bonus, the hotel happens to feature one of the best cocktail bars in the country, Spoonbar. Their cocktail program is a true farm-to-table affair. The drinks are as visually stunning as they are remarkably tasty.

Hotel Les Mars
 Hotel Les Mars Drink Me     

Location: 27 North St, Healdsburg, CA 95448
Phone: (707) 433-4211
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H2 Hotel

H2 Drink Me

Location: 219 Healdsburg Ave, Healdsburg, CA 95448
Phone: (707) 431-2202
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Spoonbar Drink Me

Location: 219 Healdsburg Ave, Healdsburg, CA 95448
Phone: (707) 433-7222
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After an evening of delectable cocktails, start your morning off with the ultimate cup of coffee from Flying Goat. They roast their own coffee and feature superb baristas. Order the Aztec Mocha and your taste buds will dance with unadulterated joy.

Flying Goat Drink Me

Location: 419 Center Street, Healdsburg, CA 95488
Phone: (707) 433-8003
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At lunch time, wander into Shed, a local marketplace with a fantastic cafe and live music. Their cafe showcases dishes made with organic ingredients and they offer a great selection of wines on tap.

Shed Drink Me

Location: 25 North St, Healdsburg, CA 95448
Phone: (707) 431-7433
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Alternatively, pop into Chalkboard, a casual dining spot focusing on the fare made with ingredients sourced from local Sonoma county farms. Executive chef Shane McAnelly’s daily menu of tapas is made with ingredients that are partly sourced form the restaurant’s own garden. Many top local wines are featured on the restaurant’s list. In addition, the cocktails are interesting and well worth ordering.

Chalkboard Drink Me

Location: 29 North St, Healdsburg, CA 95448
Phone: (707) 473-8030
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Despite Healdsburg’s seemingly diminutive size, your dinner options are quite extensive and allow the indulgence of your every mood. For a memorable dining experience, visit Barndiva, where I had the best tuna dish of the year. Great wine list and excellent cocktails seal the deal. Barndiva‘s proprietors also own Healdsburg Modern Cottages, a group of idyllic, 1930s-style cottages surrounded by olive trees. If you fancy cozy fireplaces, plush bedding and Eames Era furnishings, these chic accommodations are for you. Request a loaner bike and pedal your way through the town’s formidable charm.

Barndiva Drink Me

Location: 231 Center St, Healdsburg, CA 95448
Phone: (707) 431-0100
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Healdsburg Modern Cottages

Healdsburg Modern Cottages Drink Me

Location: 425 Foss St, Healdsburg, CA 95448
Phone: (866) 964-0110

In the mood for Italian? Scopa, a favorite hangout for local vintners, never disappoints. They turn out spectacular dishes from a postage stamp kitchen. Don’t miss the meatballs and grilled calamari.

Location: 109A Plaza St, Healdsburg, CA 95448
Phone: (707) 433-5282

Craving seafood? Willi’s Seafood and Raw Bar offers an enormous selection of small plates designed for family-style sharing. Famous for their wide variety of fresh oysters, New England-style seafood “rolls” and raw preparations, such as ceviches and tartares; it also boasts an extensive wine list to wash down these tasty morsels.

Willi's Seafood and Raw Bar Drink Me

Location: 403 Healdsburg Ave, Healdsburg, CA 95448
Phone: (707) 433-9191
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There are also thirty tasting rooms in Healdsburg, showcasing seven appellations and over twenty varieties. I visited all of them. My top five tasting rooms are:


C Donatiello

Chris Donatiello left a flourishing career as a wine and spirits marketing executive to pursue his passion for making wine in Russian River Valley. The wines are character driven, thoughtfully made, and full of bright, vivid flavors. His Windhorse Vineyard Pinot Noir is one of my favorites.
Location: 320 Center St, Healdsburg, CA 95448
Phone: (707) 431-4442

Davis Family Vineyards          

Guy Davis is a man of huge heart and equally enormous passion for grape growing and winemaking. His wines are pure, honest, true to their origin and delicious to boot.

Location: 52 Front St, Healdsburg, CA 95448
Phone: (707) 433-3858
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Hartford Family Tasting Room and Salon

 Hartford Drink Me

This is a brand new facility. It’s a spacious, beautifully appointed salon. Their Pinot Noirs and Chardonnays are phenomenal. You can read more about Hartford wines here.

Location: 331 Healdsburg Avenue, Healdsburg, CA 95448
Phone: (707) 887-8031

Valdez Family Winery

 Valdez Drink Me

An extraordinary grower who produces fruit for Mark Aubert, JC Cellars, Paul Hobbs and Pahlmeyer, Ulisses Valdez is “American Dream” personified. First generation farmer and vintner, his success is rooted in hard work and dedication. His poignant portfolio of wines is stellar and well worth a special trip.

Location: 113 Mill St, Healdsburg, CA 95448
Phone: (707) 433-3710
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Windsor Vineyards

Windsor Drink Me

This is a relaxed, casual space that features honest, good value wines. This is the only winery in California that offers customization to consumers. Win favor with friends and family by offering them a gift of wine with a personalized label.

Location: 308 B Center Street, Healdsburg, CA 95448
Phone: (707) 921-2893
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