Healdsburg Travel Guide

A perfect weekend in Healdsburg is not hard to come by. Truly you could pick any recommendation and have the most delightful weekend. Healdsburg is one of those cities that looks like a film set, the downtown is gorgeous, and every shop and restaurant oozes character. Want a weekend filled with incredible wine & fantastic food? Healdsburg is your place.

The perfect Bailey June Weekend:

First things first. Book your stay at The Cottages Healdsburg. This place is magical and feels like your own private home right downtown! We love the bohemian yet simplistic interiors. Bring a deck of cards and grab a seat on an Adirondack chair on your porch, flying goat coffee in hand, or pour a glass from the new winery you’ve just joined.

For lunch Campo Fina is a must, we’ve had just about everything on the menu, and their drinks are delicious. Any spot that serves their drinks in wine glasses is a ten in our book. The options are endless for food, but for dinner, Chalkboard hits the top of our list for a delicious dinner out.

Now it’s time to talk wineries. Want something close and easy, head to the Banshee tasting room for delicious wine and an inviting atmosphere. For more of an adventure, please make your way to three of our all-time favorites. We honestly could spend all day at Flowers Winery if they’d let us. This winery is a complete treat on the eyes and is serious design goals. The private cabanas truly transport you to an Italian villa! Second stop, make your way to Silver Oak. This winery is breathtaking. Their emphasis on sustainable and thoughtful architecture is inspiring and creates such a unique experience. After Silver Oak, head over to Medlock Ames just down the road. We highly recommend a picnic tasting experience in their dreamy garden.

The obsession doesn’t stop here. Read on for all of our favorites.

Please always make reservations and confirm your destinations are open for business.