The Top 10 Healdsburg Tours and Activities (Updated April 2024) (Updated 2024)

The Cool Destinations Top 10 Healdsburg is the original Best of Healdsburg list. These hand-picked tours, activities, and things to do have been fun-tested by travelers like you to provide the most excitement for the best prices in Healdsburg.

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1Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch
63
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...
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5 hours 30 minutes Free Cancellation
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$270
Details
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$270
Details
2Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
History Walking Tour of Healdsburg
14
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...
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1 hour 30 minutes Free Cancellation Instant Confirmation
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$45
Details
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$45
Details
3Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Healdsburg Small-Group Food and Wine Walking Tour
333
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...
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4 hours Free Cancellation
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$125
Details
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$125
Details
4Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Healdsburg Wine & Food Holiday Walking Tour
26
Offered for just five weeks each year, the Holidays in Healdsburg tours have become a cherished seasonal tradition. Experience the magic of wine country abundance enhanced...
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4 hours Instant Confirmation
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$129
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$129
Details
5Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Sonoma & Healdsburg Wine Tours
10
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...
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6 hours Hotel pickup offered Free Cancellation
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$750
Details
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$750
Details
6Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Healdsburg Wine Tasting and Food Pairing Guided Walking Tour
311
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...
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4 hours Free Cancellation Instant Confirmation
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$132
Details
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$132
Details
7Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Icon Wine & Food Pairing Experience at Williamson Wines in Healdsburg
57
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...
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1 hour 30 minutes Free Cancellation Instant Confirmation
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$66.29
Details
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$66.29
Details
8Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Healdsburg Hustle Scavenger Hunt
New To The Site!
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...
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2 hours Free Cancellation Instant Confirmation
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$27
Details
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$27
Details
9Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
Vintner's Private Wine Tasting Experience
New To The Site!
Don't just taste with a sales associate or wine guide. Get the story right from the owner/wine maker's mouth. Take the wine from the source,...
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1 hour 30 minutes Free Cancellation
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$20
Details
from
$20
Details
10Top 10 Tour Ranked using exclusive Cool Destinations data that may include activity quality, traveler reviews, overall popularity, and availability.
6 Hours Healdsburg Wine Tour with Luxury SUV
New To The Site!
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....
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6 hours Hotel pickup offered Free Cancellation Instant Confirmation
from
$750
Details
from
$750
Details