A Family-Friendly Guide to Healdsburg

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Advisor - Mary Iacono
Curated By

Mary Iacono

  • Road Trip Travel

  • Weekend Getaways

  • Family Travel

  • Food & Wine

  • Healdsburg

  • Wine Country

Advisor - A Family-Friendly Guide to Healdsburg
Curator’s statement

No trip to the Sonoma Valley can be complete without a stay in gastronomic paradise: Healdsburg, California. With fine dining options like the three-Michelin-starred SingleThread and the California-French fusion restaurant Valette, it might be easy to dismiss it as an out-of-reach destination for all but the super-wealthy, but let me take you by the hand and show you through its fairy doors.

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Where to stay in Healdsburg

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Things to do in Healdsburg

Hunt for fairy doors! I don’t know who to thank for starting this, but there are hidden fairy doors all over Healdsburg. The kiddo was enamored with the search for new fairy doors while the adults walked alongside and window shopped.

Visit the Toy Chest. This toy store only a block north of town square was like walking back in time to the early nineties. They had so many toys from my childhood that I haven’t seen anywhere else in decades, along with great new toys and complete services with gift-wrapping!

Ride a horse on the beach or the dunes with Horse’N’Around Trail Rides. This is better for the teens and above. A 90-minute ride starts at $135. When you consider the beauty of the dunes and the bay and the majesty of a good horse (mine was named Pickles) it’s worth every penny. Hot tip: according to our guide Jaxson, it’s a great spot for a proposal. He’s been witness to quite a few yeses over the years! (No nos. Of course I asked.)

Hit the bocce courts. There are many vineyards that have a court for the best sport you can play with a drink in your hand, and we can attest that it’s fun for all ages. (If you want to play where you stay, there are a number of inns I can recommend as well!)

Pack a picnic and take a ride to a vineyard for a wine tasting (for the adults) and some bocce and views for the whole family to enjoy! While you could throw a dart at a map and find a great vineyard, we found Matrix Wines to be a standout. With its country charm, bocce court and absence of a hard sales pitch, it’s a perfect pit stop on your way back into town.

Places to eat & drink in Healdsburg

Journeyman Meat Co is in the same building as SingleThread. It’s a high-end salumeria that serves the perfect sandwich. (It’s also where the bacon in your breakfast comes from at SingleThread.)

Little Saint is a plant-based eatery with live music every Thursday and a cocktail bar that will knock your socks off.

Bravas Bar de Tapas is a colorful tapas bar headed by two James Beard finalist chefs. The paella was a dream.

Quail and Condor ​​was started by bakers from SingleThread. While I personally couldn’t eat anything they had to offer, I have it on good authority that the pastries are phenomenal. And why wouldn’t they be? They use the highest quality ingredients (and also make an appearance on the SingleThread breakfast menu).

Need to know

Hot tip: Look out for a new casual eatery opening up in April right near town square called Burrow. The owners David and Elise Baeli, who used to run Southern food joint Hops & Hominy in San Francisco, are re-vamping the old “Wurst Restaurant” with a new menu in a family-friendly price range and atmosphere. I can’t wait!

Advisor - Mary Iacono

Travel Advisor

Mary Iacono

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