Healdsburg: Small-Group Food & Wine Walking Tour

Summary

Healdsburg’s flavors on foot: wine, tapas, and local stories

You’ll wander Healdsburg’s sunlit streets with a small group, tasting local wines and tapas while hearing stories from passionate guides and artisans. Expect friendly faces, unexpected flavor pairings, and plenty of laughter as you discover why Sonoma County’s food scene feels so personal—and why you might want to linger long after dessert.

What’s the experience like?

The first thing I noticed in Healdsburg was the way the morning light hit the old plaza—sort of golden, almost syrupy. Our guide, Jamie, waved us over by the bakery (the smell of bread was ridiculous) and handed out little name tags. She had that kind of voice you lean into—warm, but quick to laugh. We set off past a couple of sleepy shops and she started telling us about Pete Seghesio’s family, how his grandparents came here with nothing but a few grapevines and stubbornness. I didn’t expect to care about wine families at 10am, but somehow it felt like we were walking through someone’s living room instead of a town.

We ducked into a salumeria where the prosciutto practically melted on my tongue—honestly, I could’ve just stayed there. Someone asked if all the wines were local and Jamie grinned, “If it isn’t from around here, we don’t pour it.” The sangria at our next stop was cold and citrusy; I tried to guess the spices but gave up after my second glass. There was this moment when a winemaker came out from behind the counter just to chat—he told us about his grandmother’s recipe for focaccia and how he still can’t get it quite right. Made me think about my own family recipes back home.

Somewhere between a tea shop (I’d never had a tea mocktail before—still not sure how I feel about it) and Portalupi Wines’ porch, the group got quieter. Maybe it was the food coma setting in or maybe just that Sonoma County hush that settles in after lunch. Jamie pointed out SingleThread across the street—apparently Michelin stars don’t make you too busy to wave at your neighbors here. The whole walk was barely two miles but felt like we’d wandered further somehow. My shoes were dusty by the end and my phone full of blurry photos I’ll probably never delete.

Step-by-step itinerary

Day 1 — Healdsburg food and wine walking tour

• Welcome to Healdsburg small group tour
• Visit Healdsburg town plaza and learn history
• Stop at Italian Salumeria and Winery
• Enjoy tapas and sangria cocktails
• Taste wine and bites at Portalupi Wines
• Visit popular dessert shop
• Explore teas, tea mocktails, and sake
• Pass by 3-Star Michelin restaurant
• Discover artisan bread and baked goods
• Tour concludes with local tips and insights

Top questions

How long is the Healdsburg food & wine walking tour?

The tour lasts approximately 3.5 hours.

Are all food and wine tastings included in the price?

Yes, all tastings are included during the tour.

Is this tour suitable for vegetarians or those with dietary restrictions?

The tour can accommodate some vegetarian and pescatarian diets; note any restrictions when booking.

How many people are in each group?

The maximum group size is six people per tour.

Is there an age requirement for wine tasting?

You must be at least 21 years old with valid ID to participate in wine or beer tastings.

Does this Healdsburg walking tour include visits to wineries?

Yes, you’ll visit boutique wineries like Portalupi Wines as part of the experience.

Will we meet local winemakers or artisans on this tour?

You’ll have opportunities to meet local winemakers and food artisans along the route.

Is transportation provided for this tour?

No transportation is needed—the experience is entirely on foot within Healdsburg.

What’s included

Your day includes all food tastings—from prosciutto at a renowned salumeria to seasonal tapas—as well as boutique wine pours, a cocktail or sangria stop, plus insights from your professional foodie guide throughout Healdsburg’s walkable center.