10 Healdsburg Tours, Compared

1.Healdsburg Small-Group Food and Wine Walking Tour

★★★★★★★★★★5.0 · 433 reviews · 4 hours (approx.) · from $132Our pick

Walk Healdsburg with a local foodie guide, stopping for wine and food pairings, tapas, tea, and dessert. Groups are capped at six, and guides such as Tammy share town history, winery background, and practical tips for where to eat and explore next. The route and some stops can vary, so note dietary needs when booking.

“Tammy is a long time resident, and was well informed of all things Healdsburg. The winery/restaurants hosts were gracious and detailed in their info re: their product and its history in the region. Fabulous, educational, and an easy walk for seniors..”

Check availability →Read our full review

2.Healdsburg Wine and Food Pairing Guided Walking Tour

★★★★★★★★★★5.0 · 400 reviews · 4 hours (approx.) · from $139

Meet at Healdsburg Plaza for a four-hour walking tour with a local guide and no more than seven other people. Visit three or four tasting stops, which may include boutique wineries and a non-wine shop, with food pairings and tasting fees included. Guides who have led tours include Carol, Greg, Erica, Denee, and Harold, though your guide and stops can vary.

“Ask for Erica - Great guide - had a wonderful time and she really knew the shop owners well. Great choices of boutique wineries and good pairings at most.”

Check availability →Read our full review

3.Guided Healdsburg Wine Country Bike and Wine Tasting Tour with lunch

★★★★★★★★★★5.0 · 81 reviews · 5 hours 30 minutes (approx.) · from $209

Ride 10 to 16 miles along quiet West Dry Creek Road with a local guide, stopping at three wineries and pausing for a picnic lunch among the vineyards. Choose an e-bike or regular bike; tasting fees are extra. Guides have included Luke, Gwen, Alex, and Dustin, though your guide may differ. Groups are limited to six.

“We really enjoyed our bike tour with Alex! She kept us at a comfortable pace through the 12 miles of cycling. The wineries and olive oil/olive tasting venues were great choices and reflected the types of wine enjoyed by the 4 of us on the tour. Best of all, we had a wonderful picnic lunch at Amista Vineyards and Alex followed up after the tour, via e-mail with her recipe for her Orzo salad! Thanks Alex!”

Check availability →Read our full review

4.Icon Wine & Food Pairing at Williamson Wines in Healdsburg

★★★★★★★★★★5.0 · 72 reviews · 1 hour 30 minutes (approx.) · from $50

Spend about 90 minutes at Williamson Wines in downtown Healdsburg, tasting four limited-production wines with chef-prepared bites. Your host explains how the pairings work, and the winemaker or owner may stop by. The group is capped at eight, and the tasting costs $50 per person.

“We learned how to pair our favorite wines with our favorite foods bringing out the best flavors in both. Staff amazing and the owner stopped in and made sure to talk to everyone that was there just visiting or tasting. Wonderful winery. Became members and can’t wait to come back!”

Check availability →Read our full review

5.Healdsburg Wine & Food Holiday Walking Tour

★★★★★★★★★★5.0 · 36 reviews · 4 hours (approx.) · from $149

At 11 a.m., join a guide for a four-hour walk through holiday-season Healdsburg, with tastings at three boutique wine rooms and local food stops. Expect paired bites, wine and town stories, and a small group capped at eight. Guides on past tours have included Carol, Danae, Carrie, Harold, and Greg.

“Lovely spots in town. Food & wine pairings were fun. It was a pre-holiday activity for us. Planning another visit to Healdsburg. Many thanks.”

Check availability →Read our full review

6.History Walking Tour of Healdsburg

★★★★★★★★★★5.0 · 32 reviews · 1 hour 30 minutes (approx.) · from $45Best value

Join Healdsburg guide Linda Cook for a 90-minute walk from Harmon Guest House to the Healdsburg Museum. You’ll see a current museum exhibit, visit century-old Costeaux French Bakery, hear local history and get tips for exploring town. Tea, chocolate and local favorites add a tasty pause. Groups are capped at 10.

“What a fabulous walking tour in beautiful downtown Healdsburg! Our tour guide Linda, sure was so wonderful with her smile and she was so excited to share history about Healdsburg. I highly recommend this tour!”

Check availability →Read our full review

7.Full Day Guided Electric Bike Wine Tasting Tour with Lunch

★★★★★★★★★★5.0 · 26 reviews · 6 hours (approx.) · from $239

Start in downtown Healdsburg with guides Chris or Bill for a six-hour electric-bike tour through Dry Creek Valley. Ride 20 to 24 miles on quiet roads, stop at two or three wineries, and pause for a made-to-order deli lunch. Bluetooth helmets help you hear the guide, and pedal assist takes the sting out of hills. Tasting fees are extra.

“We had great weather, a friendly and informative guide, beautiful scenery, tasty sandwiches, personal talks with winery owners at both stops…..what more could we ask!? Oh, yes…a van picked up our purchased wine from the wineries and Chris carried our wines to our car after the bike ride. Thank you!”

Check availability →Read our full review

8.Half Day Guided Electric Bike Wine Tasting Tour with Lunch

★★★★★★★★★★5.0 · 25 reviews · 4 hours (approx.) · from $179

Bike Tour Sonoma leads a four-hour electric-bike ride from Healdsburg through scenic vineyard routes, with stops at two local wineries and a made-to-order deli sandwich lunch. Premium e-bikes, Bluetooth-connected helmets, and bike accessories are included. Guides Chris and Will have led tours, and the group is capped at eight.

“Chris went above and beyond to make our experience amazing! We loved biking in the beautiful vineyards and the wineries he took us to were charming and delicious! We can’t wait to do it again when we come back in November. Thank you Chris! Susie and Sally”

Check availability →Read our full review

9.Sonoma & Healdsburg Wine Tours

★★★★★★★★★★5.0 · 21 reviews · 6 hours (approx.)

Spend about six hours touring Sonoma wine country in a private group of up to six, with driver and guide David handling the transport and helping shape the winery stops around your tastes. Expect small producers and intimate tastings, sometimes with a winemaker. Tasting fees are extra, though some wineries may waive them.

“Visiting the different wine tastings was my favorite part. We especially enjoyed the Inman tasting. The driver, David, was nice and knowledgeable.”

Check availability →Read our full review

10.Healdsburg: Boutique Wine and Food Pairing Walking Tour

★★★★★★★★★★4.6 · 14 reviews · 4 hours · from $139

Start at Healdsburg Plaza for a small-group walk with a guide, then visit three boutique wineries for seated tastings, food pairings and, potentially, a comparison of Sonoma appellations. Finish with premium tea and local chocolate. Past guides have included Harold, Carol and Carrie; the guide and winery lineup can vary.

“We had a really fun time with Harold. He was knowledgeable on the food pairings and definitely took us outside our "comfort zone". He helped us expand our understanding of how and why certain foods pair well with certain wines. The vendors at each stop (3) were really personable and educational. My only feedback is to provide more information on the event page so people know which wineries they're visiting and what to expect. For example, there was a winery on our tour that was all Pinot. We're not big fans of red wine and it wouldn't have turned us away, but I wish we had known that would be…”

Check availability →Read our full review