Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience Healdsburg's charm with a 4-hour boutique wine and food walking tour, featuring tastings at boutique wineries, teas, chocolates, and expert guides.
Discover the Healdsburg: Boutique Wine and Food Pairing Walking Tour, a delightful half-day experience in the heart of California’s wine country. Priced at $139 per person and lasting 4 hours, this tour offers an engaging way to explore Healdsburg’s charming streets, boutique wineries, and gourmet treats. Led by a knowledgeable English-speaking guide, the tour is limited to 8 participants, making for an intimate and personalized experience.
We like how this tour combines wine tastings, food pairings, and educational moments in a relaxed setting. It’s ideal for those interested in learning simple wine and food pairing techniques that can be easily recreated at home. While the tour involves walking and standing, it’s accessible for most and offers a chance to explore Healdsburg’s historic plaza and its boutique wine scene in a small group.
However, keep in mind that pours are standard tasting amounts, not full glasses, and the tour operates rain or shine. It’s a great choice for wine lovers, foodies, or anyone curious about Sonoma County’s local artisan offerings. For those wanting a focused, educational, yet fun outing, this tour hits the right notes.


The tour begins at 10:45 AM from the Gazebo/Bandstand across from Kinsmoke Texas BBQ in the historic Healdsburg Plaza. This central location makes it convenient to meet and start exploring. The tour is designed as a half-day morning activity, perfect for those staying nearby or planning a relaxed day in town.
The meeting spot is easy to find, and the tour includes a brief orientation to introduce you to Healdsburg’s local scene before heading out to the winery stops. Be sure to bring comfortable shoes and your driver’s license for wine tastings.
If wine interests you, we've examined these other wine experiences in Healdsburg

Each of the three winery stops offers a seated wine and food pairing, where boutique winemakers host the group. This setup allows for closer interactions, giving insight into small production wines that differ from larger commercial brands. The tastings include tasty bites that complement the wines, enriching the experience.
One of the standout features is the chance to compare wines from different appellations, providing an educational look at Sonoma County’s diverse growing regions. The focus is on premium wines and artisan chocolates, which add a sweet counterpoint to the tasting journey.

Among the stops is a hidden gem, adding an element of discovery that many tours overlook. This location offers a different perspective on local wine production and often features Pinot Noir wines, which are popular in the area. The tour also includes a luxury tea tasting, providing a calming contrast to the wine sessions.
The premium teas are thoughtfully selected, and the local chocolates offer a sweet finale, making the experience well-rounded and appealing to sensory enthusiasts.

A key feature of this tour is the focus on learning easy pairing techniques that enhance your wine and food enjoyment. The guide leads the group through simple methods to understand how flavors interact, making it easy to replicate at home. This educational aspect helps expand your palate and appreciate the nuances of different wines and foods.
Many reviewers praise the knowledgeable, engaging guides who share stories and insights, making the tasting sessions informative and fun without feeling overly technical.
More Great Tours Nearby
The tour is led by a live English-speaking guide who ensures the group stays engaged and informed. The small group limit of 8 participants fosters a friendly atmosphere, allowing for personalized attention and plenty of opportunity for questions.
Multiple reviews highlight the guides’ expertise and personable nature, with some mentioning guides like Harold and Carol who make the experience memorable through their knowledge and friendliness.
Keen to taste more of Healdsburg? We've looked into these other food and drink experiences

The tour operates rain or shine, so dressing appropriately is advised. Participants should wear comfortable shoes as the experience involves walking between stops. The tour is wheelchair accessible, accommodating most physical needs, but it’s helpful to advise the provider of any specific requirements.
The pours are typical tasting sizes, around 1 to 1.5 oz, not full glasses. No pets are allowed, and guests must be at least 21 years old to participate. The meeting point is easy to find, and the tour is designed for a relaxed pace suitable for most walking abilities.

This experience emphasizes boutique wineries with winemaker hosts and a focus on food and tea pairings, offering a more intimate and educational twist compared to larger wine tours. The inclusion of artisan chocolates and premium teas** adds a special flavor to the day, appealing especially to foodies.
Unlike some tours that focus solely on wine, this one balances learning with tasting, and the small group size creates a convivial atmosphere. The flexibility of reserve now, pay later, and free cancellation up to 24 hours in advance** makes planning easy.

For those seeking a relaxed, educational, and delicious way to explore Healdsburg, this tour delivers. It’s especially suited for wine enthusiasts interested in boutique wines, food pairing, and learning simple techniques they can apply at home. The small group setting and expert guides ensure an engaging experience.
While the wine pours are modest and the schedule is paced for comfort, the tour’s focus on quality, local artisans, and personalized attention make it a worthwhile option for a half-day escape in California’s wine country.

How long is the tour?
The tour lasts 4 hours, typically scheduled in the morning.
Where does the tour start?
It begins at 10:45 AM from the Gazebo/Bandstand in Healdsburg Plaza, across from Kinsmoke Texas BBQ.
What is included in the price?
The price of $139 per person covers the guided walking tour, food, and wine tastings.
Are the wine tastings full glasses?
No, pours are standard tasting amounts, around 1 to 1.5 oz, not full glasses.
Is the tour accessible for wheelchairs?
Yes, the tour is wheelchair accessible.
Can I cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund, and you can reserve now & pay later.
What should I bring?
Bring comfortable shoes and your driver’s license for wine tastings.
Are pets allowed?
No, pets are not permitted on this tour.
What is the focus of the tasting stops?
You will visit boutique wineries, sample premium wines, enjoy artisan chocolates, and taste luxury teas.
Who is the tour suitable for?
The tour is not suitable for under 21s and involves walking, but is generally accessible for most abilities.
This Healdsburg Boutique Wine and Food Pairing Walking Tour offers a rich blend of local wine, gourmet bites, and educational insights, ideal for those wanting to enjoy a taste of California’s wine country in an intimate and relaxing setting.
You can check availability for your dates here: