Curator’s statement
Healdsburg is where Wine Country slows down and levels up. I come here to design moments—sunset tastings under redwoods, chef counter dinners, and late-night rooftop cocktails—with everything walkable from the Plaza. Between SingleThread’s rarefied hospitality and The Madrona’s painterly charm, it’s a masterclass in indulgence. Come for the Pinot and Chardonnay—stay for the ritual of beautiful days well-planned.
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Things to do in Healdsburg
Aperture Cellars estate tasting: Sleek, gallery-like space pouring terroir-driven Cabernet, Bordeaux blends, and more—reserve ahead for terrace or private lounge.
House of Flowers (Flowers Winery) “Estate Immersion”: Garden-set tasting of Sonoma Coast Pinot & Chardonnay with elevated bites, serene, design-forward setting.
Healdsburg Plaza stroll & shopping: Bounce between indie boutiques, art, and in-town tasting rooms around the leafy square—perfect no-car afternoon.
Roof 106 at The Matheson: Golden-hour cocktails and wood-fired small plates on the town’s rooftop perch—great pre- or post-dinner stop.
Spa time: Book a treatment at Montage’s spa or Spa Hotel Healdsburg for a modern, nature-inspired reset.
Fitch Mountain: Easy local hike with river and forest views—start your morning with birdsong and end with bubbles.
Russian River paddling: Calm-water kayak/float days are classic here—pack a picnic and drift under willows between vineyard views.
Places to eat & drink in Healdsburg
SingleThread Restaurant: Three Michelin stars and a Green Star—impossibly thoughtful kaiseki-inspired tasting menu rooted in the restaurant’s own farm. Book far in advance.
Valette: A love letter to Sonoma’s producers—lively room, house-cured charcuterie, and a can’t-miss scallop “en croûte.”
The Matheson: Seasonal, wood-kissed wine-country cuisine—then head upstairs to Roof 106 for nightcaps by the fire pits.
The Madrona Restaurant: Candlelit, garden-driven plates inside a storied mansion—ideal for a romantic dinner or long brunch.
Quail & Condor: Beloved artisan bakery for laminated pastries and morning fuel before the vines (pair with an itinerary-heavy day). (Context: also pops up in local hotel programs.)
Need to know
Book tastings & top tables early. SingleThread, Flowers, and prime weekend slots fill weeks to months out.
Go car-light. If you plan to taste, let me arrange a driver or rideshare—many highlights cluster around the Plaza, so walking is easy.
Seasonal savvy. Spring wildflowers and late-Sept harvest are peak—mid-summer afternoons run warm—build in pool or spa time.
Plaza first, valleys next. Start downtown, then branch out to West Dry Creek and Alexander Valley for contrast (sleek modern estates vs. rustic charm).
Travel Advisor
Lucas Wackford
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For more inspiration and insider recommendations, visit our Healdsburg page.