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Tour Overview

Tour Photos & Videos


  • Picturesque Gazebo in the heart of Healdsburg Plaza
  • A selection of thumbprint cellars' wines with their famous branding
  • thumbprint's stylish Tasting Lounge is an experience in itself!
  • Award-winning Calistoga Olive Oil Co has just opened a store in Healdsburg
  • Williamson Wines have garnered a fantastic reputation in Wine Country.
  • Delectable Chocolates on display...
  • Enjoy Small Bites Paired with Sonoma Wines
  • Enjoy Sonoma Farm Goods
  • Portalupis Charming Tasting Room
  • Delight in 6 Award Winning Portalupi Wines.
  • Local artisan chocolate tasting.

Healdsburg Wine & Gourmet Food Lovers Tour

This is a food & wine lover’s dream tour offered by Wine Country Walking Tours. Enjoy this fun filled 4-hour guided walking tour, taking in all the gourmet highlights in the charming Sonoma County town of Healdsburg . You’ll meet your Wine Country Walking Tour Guide in Healdsburg Plaza at 11:00am, and begin with a brief orientation of the town, as your guide brings you to the best French bakery outside of France. We will then head to your first of three winery visits, Portalupi. At their tasting room, you’ll enjoy a private seated wine and food paring complete with perfectly-paired tasty bites and a traditional Port. Thereafter it’s on to thumbprint cellars’ stylish Tasting Lounge for appellation comparison of Cabernet Sauvignon. Next you’ll visit the Healdsburg Olive Oil Company, for a guided tasting of their luscious, award-winning olive oils. Williamson Wines is the next stop, where you’ll be treated to a unique, seated tasting of six wines, paired with delectable cheeses. Finally, you’ll visit the Healdsburg General Store for an indulgent chocolate tasting!

All Wine Country Walking Tour Guides are highly knowledgeable & friendly Sonoma County locals. Tours are kept to a maximum of 8, to insure an intimate and enjoyable experience for all. Healdsburg is very compact – actual walking required is minimal! All tasting fees are included in the walking tour price!

CHECK AVAILABILITY: Table Below Shows How Many Spaces Are Left!

Tour availability is NOT being updated daily. Please contact Wine Country Walking Tours directly at 707-758-4725 or  for availability and reservations. Thank you.

Times & Booking Info:

  • This Wine Country Walking Tour is available at 11:00 am Monday - Sunday
  • Book at least 24 hours in advance
  • Minimum Group Size: 2. Maximum Group Size: 8 (Please call us for groups larger than 8)
  • Have Questions? Call us on 707-758-4725

Wine Booking Details

Cost: Call for Pricing
Times: 11:00 AM
Duration: 4 hours
Location: Healdsburg
Must Book By: 24 hours in advance

Package Includes

  • Guided Walking Tour of Charming Healdsburg
  • Local Artisan Cheese Tasting
  • Private Seated Tasting of award winning Italian varietals at Portalupi Wines
  • Appellation Comparison Tasting at thumbprint cellars
  • Healdsburg Olive Oil Company Guided Tasting
  • Seated Wine & Cheese Pairing at Williamson Wines
  • Chocolate Tasting
  • All Tasting Fees are Included!

What We Like Best

**These tours are wonderful gift giving ideas for the holidays, birthdays weddings and more!**
This tour is truly unique in Wine Country. All Wine Country Walking Tour guides are friendly Sonoma County locals. Guide knowledge is exceptional and no other tour provides such a diverse & exciting line-up of local, gourmet Artisans.