The 15 best things to do in Healdsburg (2026)

The ranked list

1. 

   1. Healdsburg Small-Group Food and Wine Walking Tour

   Outty Ranking92

   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 92/100, 5.0/5 from 448 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 Ranking89

   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 89/100, 4.9/5 from 421 traveler reviews, 4h from $139, free cancellation.

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3. 

   3. 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 85 traveler reviews, 5.5h from $209, 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 38 traveler reviews, 1.5h from $45, free cancellation.

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5. 

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

   Outty Ranking77

   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 77/100, 5.0/5 from 56 traveler reviews, 4h from $169, free cancellation.

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6. 

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

   Outty Ranking77

   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 77/100, 5.0/5 from 42 traveler reviews, 6h from $199, free cancellation.

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7. 

   7. 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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8. 

   8. 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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9. 

   9. 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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10. 

    10. 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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11. 

    11. 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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12. 

    12. Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4

    Outty Ranking57

    This Healdsburg-focused wine tour promises a day filled with exceptional wines, picturesque vineyards, and delectable culinary experiences, all within the delightful timeframe of 6 hours. This is a black SUV, holds up to. Worth a Look at 57/100, 5.0/5 from 3 traveler reviews, 6h from $599, free cancellation.

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13. 

    13. Deep Space Night Sky Tours in Sonoma County

    Outty Ranking55

    Discover the universe in the serene setting of Sonoma County during our Premium Deep Space Night Sky Tours. Located in the picturesque Dry Creek Valley, just a short drive from Healdsburg, these tours offer unparalleled. Worth a Look at 55/100, 5.0/5 from 1 traveler reviews, 1.3h from $96, free cancellation.

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14. 

    14. Healdsburg Wine Country Electric Trike and Wine Tour 3 Hours

    Outty Ranking53

    Your guide leads a relaxed electric trike ride that begins at Bacchus Landing, a vibrant Healdsburg gathering place with seven boutique wineries. Drive eco-friendly electric trikes and follow the professional tour guide. Worth a Look at 53/100, 3h from $175, free cancellation.

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15. 

    15. Healdsburg 6 Hour Private Wine Tour Feat. Coppola Winery, holds 4

    Outty Ranking50

    This Healdsburg-focused wine tour promises a day filled with exceptional wines, picturesque vineyards, and delectable culinary experiences, all within the delightful timeframe of 6 hours. This is a black SUV, holds up to. Worth a Look at 50/100, 6h from $649, 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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