
Healdsburg Wine & Food Holiday Walking Tour
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Highlighted days have spots open. Grey days are sold out or not running.
September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 37 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Healdsburg Wine & Food Holiday Walking Tour worth booking?
Healdsburg Wine & Food Holiday Walking Tour is a 4-hour experience in Healdsburg, United States, from $149 per person. It scores 78 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.9/5 rating across 37 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 78 / 100
- Rating
- 4.9/5 (37)
- Duration
- 4 hours
- From
- $149 per person
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
What you get
About this experience
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 these guided wine and food pairing walking tours of charming downtown Healdsburg. Enjoy private seated tastings of wines paired with delicious bites from Healdsburg restaurants or local food purveyors, freshly baked artisan desserts, aromatic spiced teas, chocolates and so much more. Come experience the holidays with us in Healdsburg, it's reminiscent of the times found in a Charles Dicken's novel.
What's included
Included
- Perfectly paired light bites for your wine & food pairing from local restaurants or food purveyors
- Professional Guide
- All tasting fees are included
- Wine discounts available at select stops
- Custom crafted wine & food pairings at 2 or 3 boutique tasting rms and a non-winery experience
Not included
- Hotel pickup and drop-off
- Gratuity
Where it starts and ends
Meeting point
Healdsburg
Healdsburg, California, United States
At the GAZEBO located in the Healdsburg Plaza. The Healdsburg Plaza is located at Matheson and Center Street. Parking: Free Public parking available behind Hotel Healdsburg located at 25 Matheson Street.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Healdsburg · Healdsburg, California, United States
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Wine Country Walking Tours
Know before you go
- Wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Minimum drinking age is 21
- Please advise any specific dietary requirements in the "Special Requirements" field at time of booking
Photos






What travelers are saying
Outty’s summary of the themes that recur across 37 traveler reviews. Written by us, not quoted from reviewers.
The guide
9 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
8 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
6 mentionsReviewers describe the commentary as informative rather than scripted.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
37 verified traveler reviews for Healdsburg Wine & Food Holiday Walking Tour. Ratings and reviews provided by Viator and Tripadvisor.
Girls wine trip in April, 2026
Denee' was wonderful. The venues we visited were awesome. It was a great day of fun, food and wine. I would recommend the tour. We visited three winery's and a honey shop. Everything was wonderful. Again, Denee' was an awesome tour guide. Very knowledgeable
via Tripadvisor
Outstanding day in Healdsburg!
One of the best tours I have taken. Denee was such a great host and picked absolutely wonderful stops for our Food/Wine tour. Highly recommend this experience
via Tripadvisor
Another Unforgettable Wine Tasting Experience with Carol
This was our second time on the wine-tasting tour, and we couldn’t be happier that we returned! Last year, we celebrated our anniversary in Healdsburg and our tour guide was Greg, and he made the experience so special that we knew we had to come back. This time, Carol was our guide, and she was just as exceptional. Her deep knowledge of wine, warm personality, and passion for the region made the day even more enjoyable. The wines were, as always, incredible, and Carol’s thoughtful recommendations really enhanced our experience. We love the town, the people, and the overall wine-tasting experience, which is always elevated by the genuine hospitality of the guides. Carol’s engaging storytelling and attention to detail made the tour feel personal, and she took the time to ensure we were comfortable and having a great time. This tour has become a must-do for us whenever we're in the area, and we’re already looking forward to our next visit. Thanks again for making our anniversary special last year, and for another unforgettable experience this time around!
via Viator
Wine tasting in Healdsburg December 2024
Our tour guide was amazing 👏 and I would totally do it again and would recommend the same tour guide for sure.
via Viator
Great wine tasting experience!
What a great tour! We went to 3 boutique tasting rooms and a tea house. Each had a unique story with staff that was knowledgeable and very enthusiastic of their product. Our guide, Danae, was a great host. She provided us with great insight and suggestions for our stay in Healdsburg. I would 100% recommend this tour!
via Viator
Good to know
- Duration
- 4 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 13
- Verdict
- Strongly Recommended
Why this scores 78
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Healdsburg Wine & Food Holiday Walking Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Healdsburg.
How much does Healdsburg Wine & Food Holiday Walking Tour cost?
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Prices start at $149 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Healdsburg usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Healdsburg Wine & Food Holiday Walking Tour take?
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Plan for about 4 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Healdsburg is not rushed.
Is Healdsburg Wine & Food Holiday Walking Tour worth it?
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It holds an Outty Ranking of 78 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 37 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Healdsburg, and how flexible the cancellation terms are.
Can I cancel or reschedule Healdsburg Wine & Food Holiday Walking Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Healdsburg Wine & Food Holiday Walking Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 4-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Healdsburg Wine & Food Holiday Walking Tour?
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Around 13 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Healdsburg can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Healdsburg and add a light layer if any part of the 4-hour experience runs outdoors or after sunset.
Where does Healdsburg Wine & Food Holiday Walking Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Healdsburg within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Healdsburg?
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Healdsburg, CA packs its best experiences into walkable neighborhoods, local food, and day trips nearby. Outty ranks every bookable tour and activity in Healdsburg by rating quality, review depth, booking demand and value, so you can see the standouts before you book. On Outty we rank every Healdsburg experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Healdsburg Small-Group Food and Wine Walking Tour, Healdsburg Wine and Food Pairing Guided Walking Tour, Sonoma Horseback-Riding Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Healdsburg?
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Spring and fall bring the best weather and lighter crowds in Healdsburg, while summer has the widest choice of tours and evening activities. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Healdsburg?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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