A Summer Weekend in Healdsburg

This weekend’s last minute escape to Healdsburg was a highlight of quick trips this year. I’ve been three times since last fall, so I’m still learning my way around, but have plenty of favorites to share! We booked an Airbnb, made a couple of reservations, and looked forward to the 88º forecast. We drove up on Friday night after work and arrived in time to drop our bags, freshen up, and made our way over to Chalkboard for dinner. It came highly recommended and it won us over quite quickly (read: pretzel bread and cheese). It’s a shared plate style restaurant, and everything we ordered was delicious. We got the pretzel bread, roasted cauliflower, and linguine (amazing). The restaurant is on the bottom of Hotel Les Mars, a beautiful Relais Chateaux hotel. We’re actually staying here in December, I can’t wait!

A reader fortuitously emailed me on Friday afternoon before we left, asking advice on what to do in Healdsburg. She had mapped out a day and asked me if she was missing out on anything. She basically had the same itinerary as us, but one thing on her list was Papapietro Perry Winery. I had never heard of it, but when I found out Pinot Noir is their bread and butter, I made a note. We spotted a bottle on Chalkboard’s wine list that night, so decided to try it. Hallelujah for readers who email me and tell me about stuff like this, that wine is a thing of beauty! More on this topic later in the post…

You can see my whole Healdsburg travel guide here.

For dinner, I wore:
Ulla Johnson top (selling out quickly most places, it’s my new absolute favorite if you’re looking to treat yourself, I highly recommend!), RE/DONE denim skirt (love this. I ended up cutting an inch off because it was a bit long on me), Charlotte Stone heels (so comfortable, and they come in several hues!)

On Saturday morning, we milked having a later check-out and stayed in bed longer than usual. It was so fun waking up to roosters (although, Scout may disagree with me on this one). We made our way over to Dry Creek General Store for coffee and breakfast to go and came back to enjoy breakfast under the sun while we read. It was already 75º at 10 am. Yes pleaseeeeeeee.

After an easy morning, we got ready, packed our bags, said our goodbyes to our new horse friends, and headed off to our first tasting. We hold UNTI high up on a pedestal, and can’t go to Healdsburg without a visit. Their tasting room is intimate and extremely beautiful. Windows cover each wall, all overlooking the surrounding vineyards. Their wine is some of our favorites out there, we ended up buying two bottles. We love their Syrah, but everything is honestly fantastic.

What I wore to tastings:
Rails top (I think this pattern may be sold out, but they have a few different other options), RE/DONE denim skirt, Polo Ralph Lauren “Lennox” bag (new favorite and it comes in a few other colors)

{ note to self: acquire as many wine making books as we can… step 1 to our future winery. }

After UNTI, We had some time to kill before heading to our lunch reservation at Barn Diva. Papapietro Perry was still tempting me as it was just a short 2-minute drive down the road, so we went for it. Matt and I selected different flights so we could try as many as we could. We already loved the Pinot we had tried the night before, and the kind man who worked there told us “you haven’t seen nothing yet“! He was right… every sip was heavenly. Their wines are what all our Pinot dreams are made of. So! We joined the wine club and left with six bottles. Success!! Below is a photo of their wine club balcony. I love the unexpected! We were thinking about joining Banshee but realized we have access to their wines pretty easily (I talked about my favorite market wines last week here). Discovering this spot felt extra special. We both loved the wines, so it was an easy choice for us. We can’t wait to come back soon!

After our last tasting, we were ready for lunch. Barn Diva is a loved spot on the plaza, and if you can snag a seat on the back patio, I recommend it! We ordered the heirloom tomato BLT with frites and lavender lemonade. Those frites were on another level. They’re an addicting hybrid of a potato chip and a french fry. Mouth watering just thinking about them. Definitely a favorite spot on my list.

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  1. We LOVE Healdsburg as well (drive or fly from Oregon). If you want to add to your wine list… Reeve (started by former Banshee partner and by appointment only) – beautiful setting with two properties to rent for stay, small collection of wines but ALL beautiful… and Quivera Winery, all organic, beautiful property with planting garden, and (along with Reeve) one of the few wineries where all tastings are your favorite.

    1. Someone else mentioned Reeve, I’m adding that to my list for our next trip. Thank you! Both sound amazing, already want to go back!

  2. I love this post. Beautiful pictures! I can’t wait to go next month. Thank you!

  3. I would love your advice on wonderful air b+bs in Healdsburg! I’m planning a sisters’ long weekend for this summer and have never been before. So excited! Your post is amazing! Thanks for all your insightful information!

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