The 15 best things to do in Healdsburg (November 2026)

The ranked list

1. 

   1. Healdsburg Small-Group Food and Wine Walking Tour

   Outty Ranking91

   Discover what makes Healdsburg one of Sonoma County's hottest destinations on this 3.5-hour food and wine walking tour of Healdsburg. Your local guide will share great food, wine, and a cocktail as you dine through this. 90+ Club at 91/100, 5.0/5 from 452 traveler reviews, 4h from $133, free cancellation, an Outty 90+ Club member.

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2. 

   2. Healdsburg Wine and Food Pairing Guided Walking Tour

   Outty Ranking88

   This is Healdsburg's “original” Wine & Food Pairing Walking Tour. Our 4-hour guided taste adventure, hits all the gourmet highlights of charming Healdsburg, the hippest town in Wine Country! Join us to experience the art. Exceptional at 88/100, 4.9/5 from 422 traveler reviews, 4h from $139, free cancellation.

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3. 

   3. Half Day Guided Electric Bike Wine Tasting Tour with Lunch

   Outty Ranking79

   Embark on a guided electric bike wine tour through Sonoma County with an experienced tour guide. Cruise through vineyards along scenic routes on zippy e-bikes, stopping at two top local wineries to taste the exceptional. Strongly Recommended at 79/100, 5.0/5 from 75 traveler reviews, 4h from $169, free cancellation.

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4. 

   4. History Walking Tour of Healdsburg

   Outty Ranking78

   A great 90 minute introduction to the fascinating history of Healdsburg. Where else can you learn about history, get recommendations for shopping, art galleries, wine tasting, and restaurants and spend the day outside in. Strongly Recommended at 78/100, 5.0/5 from 40 traveler reviews, 1.5h from $45, free cancellation.

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5. 

   5. Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

   Outty Ranking78

   On this moderate bike tour, we ride approximately 15 miles (24 km) in picturesque Dry Creek Valley, home to the town of Healdsburg. As you cycle through the countryside, your local, professional guide will tell you about. Strongly Recommended at 78/100, 4.9/5 from 87 traveler reviews, 5.5h from $209, free cancellation.

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6. 

   6. Full Day Guided Electric Bike Wine Tasting Tour with Lunch

   Outty Ranking78

   Embark on a guided electric bike wine tour through Sonoma County with an experienced tour guide. Cruise through vineyards along scenic routes on zippy e-bikes, stopping at two top local wineries to taste the exceptional. Strongly Recommended at 78/100, 5.0/5 from 45 traveler reviews, 6h from $199, free cancellation.

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7. 

   7. Sonoma Horseback-Riding Tour

   Outty Ranking77

   Experience Wine Country's largest and most beautiful park on horseback on this 90-minute, guided, small-group tour. Discover hundreds of acres of vineyards and the crystal blue waters of Lake Sonoma. Enjoy the rugged and. Strongly Recommended at 77/100, 4.9/5 from 307 traveler reviews, 1.2h from $129, free cancellation.

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8. 

   8. Icon Wine & Food Pairing at Williamson Wines in Healdsburg

   Outty Ranking76

   Bring friends and loved ones along for an intimate wine-tasting experience at the Williamson Wines tasting room in Downtown Healdsburg. Your expert host will guide you through five fine wines that are perfectly paired wi. Strongly Recommended at 76/100, 4.8/5 from 82 traveler reviews, 1.5h from $50, free cancellation.

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9. 

   9. Healdsburg Wine & Food Holiday Walking Tour

   Outty Ranking74

   Offered for just five weeks each year, the Holidays in Healdsburg tours began in 2011 and have become a cherished seasonal tradition. Experience the magic of wine country abundance enhanced by small-town holiday cheer on. Strongly Recommended at 74/100, 4.9/5 from 37 traveler reviews, 4h from $149, free cancellation.

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10. 

    10. Guided Kayak Tour on Russian River

    Outty Ranking69

    Embark on a unique tour of California Wine Country! Hop in a kayak for a full tour along the warm, clean Russian River in Healdsburg. The tour guide will take you through a beautiful scenic route and point out native wil. Solid Choice at 69/100, 5.0/5 from 16 traveler reviews, 5.5h from $250, free cancellation.

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11. 

    11. Private Napa or Sonoma Wine Tour—Your Day, Fully Planned

    Outty Ranking63

    Craft your perfect day in Wine Country. Tailored tours, hidden gems, and genuine hospitality. Let me be your guide. Unlike most wine tours, I fully customize the experience for each guest, ensuring they have the best d. Solid Choice at 63/100, 5.0/5 from 14 traveler reviews, 7h from $850, free cancellation.

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12. 

    12. Sonoma & Healdsburg Wine Tours

    Outty Ranking62

    Visit the wineries you know and love, or let us help you build a customized experience away from the crowds. With over 18 years in the industry, we have special access to many of the small, boutique wineries, crafting th. Solid Choice at 62/100, 4.9/5 from 23 traveler reviews, 6h from $745, free cancellation.

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13. 

    13. Wine Tour Pros - Sprinter Van Wine Tour: Up To 14 Guests

    Outty Ranking62

    Privately Driven Wine Tour Experience! We will welcome you in one of our luxury vehicles ready to go on your Napa wine tour adventure! Explore the best wineries in Napa Valley while finding out some of its secrets. Yo. Solid Choice at 62/100, 5.0/5 from 45 traveler reviews, 6h from $1,300.

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14. 

    14. Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide

    Outty Ranking61

    Drive Sonoma County yourself, with a GPS audio guide that plays automatically as you go. Your booking unlocks the whole region in the free Wine Trails app: pick your date and starting point — Sonoma Plaza, Healdsburg, Sa. Solid Choice at 61/100, 2h from $40, free cancellation.

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15. 

    15. Healdsburg Hustle Scavenger Hunt

    Outty Ranking61

    Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Aust. Solid Choice at 61/100, 3.0/5 from 2 traveler reviews, 2h from $29, free cancellation.

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Traveler ratings are provided by Viator and Tripadvisor. The Outty Ranking is our own independent evaluation. How the ranking works.

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