A family weekend itinerary: Healdsburg

Temperatures looked daunting (106º!) but between the breeze and days spent in the pool, it was perfect. We stayed at the Reeve Villa last fall and fell in love with its charm. Located just a quick drive from Healdsburg Square and basically next door to some of our favorite local haunts (Papapietro Perry, Unti, and Dry Creek General Store)—and not to mention, the Reeve tasting room right down the driveway!

We became Reeve members after our first tasting experience. We adore the owners, Kelly and Noah (the nicest people) and their portfolio of wines. It's such a vibe—good tunes always playing and a backdrop of a beautiful courtyard shaded by old oaks. A view of vineyards and their sweet goats and chickens. They bring out a delicious cheese plate when you visit for a tasting during the week—and wood-fired pizzas on weekends!

In case you want to try out Reeve, definitely make a tasting res if you can—in the meantime, some of my favorites of theirs available to buy online at the moments: Rosé | Remy Saves the Sea | Ya Moon Pinot

I thought I would share how we spent our time as we love visiting the area and have cultivated some very favorite spots. Here's how we did Healdsburg this trip, you can see my whole guide on the area here.


The Reeve Villa if you can finagle a reservation! It is such a dream.


Upon arrival we had a little tasting on property, which was lovely as always! And then made our way up to the villa for an early evening swim! We picked up pizzas from Diavola for dinner which were 10/10.

The next morning we drove over to Dry Creek General Store for a coffee and breakfast to go. The breakfast sandwich is not to be missed (add bacon and opt for the croissant if you really wanna live). I love picking up more specialty item things, too while there—like cheese board fix-ins.

After we ate, we stopped by Costeaux Bakery (another breakfast/coffee option while there!) as I preordered cakes for the bdays we were celebrating. The cheesecake I got for Matt's birthday was the highlight!

We had an 11am tasting at one of our favorite wine clubs, Papapietro Perry. If you are a very big pinot fan, you must go here.

Matt ran back to Dry Creek that afternoon to pick us up some sandwiches for a poolside lunch.

We went to Molti Amici for dinner that evening, always a treat. This has become our very favorite local spot. A can't miss!

The next day, to make it easy and because of the kids/heat, we spent most the day in the pool so repeated our breakfast and lunch routine.

That night we drove over to The Madrona for dinner. Obsessed with this spot! So charming and fun. We went for Matt's birthday and I'm so glad we did. We will be back (and will be booking a stay in the future too!).

It was a low-key trip—full of sunshine, celebrations and delicious wine and food—enjoyed every second of it!

A snap from Matt's 40th birthday dinner!

The most magical view from the pool deck at the villa.

Kelly recommended ordering pizza from Diavola... so good. A new must on my list, added to my Healdsburg guide!

Love that Reeve is family-friendly. Grace is so easy-going and loves exploring new surroundings, a treat to be able to take her to so many places with us.

Snacks at our Reeve tasting.

My Dry Creek haul!

Walking up to Madrona.

We love you, Healdsburg!

Share this story

Comments Expand -
Add a Comment

Your email address will not be published. Required fields are marked *