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Top Things to Do in Healdsburg

We compared all 5 experiences in Healdsburg so you can choose in minutes — real prices, verified reviews and our editorial picks.

4.9 5 experiences from US$ 50 Free cancellation on most experiences
Healdsburg: Small-Group Food & Wine Walking Tour
Healdsburg: Small-Group Food & Wine Walking Tour★★★★★★★★★★ 4.96 (447)4hYou’ll wander Healdsburg’s sunlit streets with a small group, tasting local wines and tapas while hearing stories from passionate guides and artisans. Expect friendly faces, unexpected flavor pairings, and plenty of laughter as you discover why Sonoma County’s food scene feels so personal—and why you might want to linger long after dessert.Free cancellationTravelers' pickMost bookedfromUS$ 133View ›
Healdsburg Wine and Food Pairing Walking Tour
Healdsburg Wine and Food Pairing Walking Tour★★★★★★★★★★ 4.90 (420)4hA 4-hour guided walking tour of Healdsburg that pairs wines from local boutique wineries with food, starting at Healdsburg Plaza at 11 am. You visit 3 to 4 tasting locations, learn pairing techniques from a live guide, and all tasting fees are included. Minimum age is 21; meet at the Gazebo in the Plaza 15 minutes early.Is it for me?Book this tour if you have a free afternoon in Healdsburg and want to learn how wine and food pairing works without paying separate fees at each tasting room. The fixed 4-hour schedule and included tastings mean you move through the town's highlights without stopping to negotiate prices or figure out where to go next.Free cancellationTravelers' pickfromUS$ 139View ›
Santa Rosa: Lake Sonoma Horseback Riding & Wine Country Views
Santa Rosa: Lake Sonoma Horseback Riding & Wine Country Views★★★★★★★★★★ 4.92 (302)1h 10m–1h 30mYou ride 90 minutes through mountain trails above Lake Sonoma with views into Dry Creek Valley, Sonoma's oldest wine region. The guide handles pacing and safety while you take in the terrain from horseback — a vantage point you can't get any other way. Helmet, water, parking and on-ride photos are included; you leave bags behind and wear closed-toed shoes. Groups stay small, and the whole outing fits into a morning or afternoon without eating your whole day.Is it for me?Book this if you want to see Wine Country from a perspective you can't get from a car, and you're comfortable spending 90 minutes on horseback at a steady pace. The small-group format and included photos mean you experience the ride instead of managing logistics.Free cancellationTravelers' pickfromUS$ 129View ›
Healdsburg: Bike tour with wine tasting & lunch in Dry Creek
Healdsburg: Bike tour with wine tasting & lunch in Dry Creek★★★★★★★★★★ 4.89 (83)5h 30mYou’ll pedal quiet backroads near Healdsburg with a local guide, stopping at three small wineries for tastings and stories. Enjoy a picnic lunch among the vines and soak up Sonoma’s laid-back pace — plus plenty of time to chat with locals or just take in the valley views you’ll remember long after the trip.Free cancellationfromUS$ 209View ›
Healdsburg: Williamson Wines Food Pairing & Tasting Experience
Healdsburg: Williamson Wines Food Pairing & Tasting Experience★★★★★★★★★★ 4.79 (81)1h 30mYou’ll sit down in Healdsburg’s relaxed tasting room and sample five wines paired with chef-made tapas—from flatiron steak to salted chocolate shortbread—while your host shares stories about Sonoma’s winemaking quirks. Expect laughter over new flavors and small surprises with every bite. This is more than just a wine tasting; it’s a slow afternoon that lingers long after you leave.Free cancellationTravelers' pickBest valuefromUS$ 50View ›
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