Healdsburg Wine & Food Walking Tour: 4-Hour Tastings

Four hours tasting wine and holiday food through a small town that feels like a Dickens novel

A guided wine and food pairing walking tour through downtown Healdsburg, offered only during the five-week holiday season, where you taste at three boutique tasting rooms and local food stops with private seated tastings and light bites. The tour runs four hours and includes all tasting fees. A professional guide leads the group through Healdsburg Plaza and the surrounding downtown, where holiday decorations, carolers and a Christmas tree set the backdrop. Minimum age is 21.

The experience

You arrive in Healdsburg during the five weeks each year when the town fills with holiday spirit: street decorations, festive window displays, horse-drawn carriages, Christmas carolers, and a lit tree in the historic Plaza. The walking tour starts here and moves through downtown, stopping at three boutique tasting rooms where you sit down for wine and food pairings designed to show how certain wines taste better with specific foods. Between the tasting rooms, you visit local food artisans and a restaurant for light bites and sips. The whole experience takes four hours.

What you taste comes from Healdsburg restaurants and local food purveyors: freshly baked artisan desserts, aromatic spiced teas, chocolates, and carefully paired wines at each stop. All tasting fees are included, and the guide leads you through the pairings, explaining the choices. Wine discounts are available at select stops if you want to buy bottles to take home. The tour has been running since 2011 and suspends the company's regular schedule each year to focus only on these seasonal tours.

What’s included

• Professional guide leading the group.
• private seated wine and food pairings at three boutique tasting rooms.
• light bites from Healdsburg restaurants and local food purveyors.
• freshly baked artisan desserts, spiced teas and chocolates.
• all tasting fees.

Before you book

Days and timesEvery dayDeparts at 11:00Last departure this season: 31 Dec

Book up to17h before

AgesAdult (21 to 90 years) · Under 21: can't be booked

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 8 days ago

Good to know

Low physical effortWheelchair accessiblePets welcomePublic transport nearbyNot recommended with heart problems

Operated by Wine Country Walking Tours

Is this one for you?The four-hour commitment leaves room for a meal elsewhere in town or time to explore Healdsburg's shops and galleries on the same day, but rules out combining it with a winery visit outside downtown or a long drive to another destination.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

When does the Holidays in Healdsburg tour run each year?

The tour operates for five weeks during the holiday season, typically from late November through December. It's a seasonal offering that the tour company runs instead of its regular schedule during this period.

What happens at each of the three tasting rooms on the tour?

You sit down for private wine and food pairings at each boutique tasting room, tasting wines paired with light bites from local restaurants and food purveyors. The guide explains how the wines and foods complement each other.

Is this tour wheelchair accessible?

Yes, the tour is wheelchair accessible. Public transportation options are also available nearby if you need them to reach the starting point in downtown Healdsburg.

What if I have dietary restrictions or allergies?

You can advise any specific dietary requirements in the Special Requirements field when you book, and the tour operator will work with you on accommodations at the food stops.

Does the tour price include everything I'll taste?

All tasting fees are included in the tour price. Wine discounts are available at select stops if you want to purchase bottles, but tastings themselves are covered.