Best Walking Tours in Healdsburg 2025

Healdsburg , California

From $ 139.00

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 town in Wine Country! Join us to experience the art of Wine & Food Pairing in a fun, casual way. Discover why certain wines taste better with specific foods. We’ve partnered with local wineries & chefs, to offer you a wonderful arrangement of unique tastings. Meet your Guide in Gazebo in the Healdsburg Plaza. After a brief orientation of town, you’ll be on to your first winery visit where you’ll enjoy a private seated wine & food pairing. You'll continue your adventure to enjoy another tasting of boutique wines creatively balanced with simple foods. Each pairing will make you rethink the way you experience food and wine. Listen to the winemakers & their families as they share their stories, passion and unparalleled love of the fertile land they call home. Come "Walking" with us and discover the best of Healdsburg!

Healdsburg , California

From $ 149.00

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 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.

Healdsburg , California

From $ 45.00

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 tasting, and restaurants and spend the day outside in the fresh air. You'll walk the streets with an experienced guide who will answer your questions and go at the only suitable pace for this city WALKING! You'll get an overview of the city, her history and the people that have made Healdsburg a destination for travelers since it's founding day. Discover why The Healdsburg Walking Tour is the best in town.