STAY

• The Madrona - a beautiful boutique hotel located just a short drive from Healdsburg town (~5 minutes). It’s housed in a historic mansion that has been restored, and the interiors, especially in the main building, are beautifully done. It has an upscale antique feel. There’s a really tasteful drawing room and a great bar for guests to hang out in, as well as a swimming pool (nothing to write home about, but nice to have) and a gym. The breakfast during the week is underwhelming, but on the weekend they have a quiche that is all time.

• H2Hotel: the most budget friendly on the list. It’s in a great location (right in town) and is clean, simple and minimalistic. H2Hotel has the same ownership as Hotel Healdsburg and Harmon Guest House.

• Hotel Healdsburg

• Harmon Guest House

• Montage Healdsburg

EAT

• Dinner

  • Barndiva - really cute place (think farm vibe with string lights) with great food and would be what I’d recommend for dinner if you only have one night.

  • Valette - upscale restaurant with delicious food.

  • SingleThread - Michelin star restaurant that serves a 10-course tasting menu. They have a rooftop, and I’d recommend going there for a drink and an appetizer, and then going somewhere else for your full dinner (unless you want to do the tasting menu).

  • Chalkboard

  • The Madrona - good food served in a beautiful setting. I’d recommend eating inside so you can enjoy the decor.

  • Diavola - located outside of Healdsburg in Geyserville, which feels like an old western town. Really delicious pizzas and cute outdoor ambiance (think twinkly lights and candles).

• Lunch

  • Oakville Grocery - great lunch sandwiches.

  • Little Saint - a vegan restaurant in the heart of Healdsburg. It’s got a quirky vibe (think eating in an antique-y living room) but the food is really good, especially the flatbread.

  • Dry Creek General Store - a general store that’s been around since 1881 and feels like you’re back in time. Great sandwiches and premade salads.

• Coffee + treats

  • The Nectary - smoothies.

  • Noble Folk Ice Cream & Pie Bar.

  • Flying Goat Coffee - matcha is amazing.

DRINK (i.e. vineyards)

• Kistler - an amazing tasting with great wine, atmosphere and snacks.

• Flowers - beautiful outdoor seating area (feels a little Restoration Hardware-esque) and I loved the snacks that they brought with the tasting.

• Silver Oak - great red wine, beautiful views and the architecture of the building is really cool. FYI there is no service so it’s hard to call ubers - we almost got stuck there!