Weekend Guide to Healdsburg, California

We usually pop over to Wine Country once a month or more. Our go-to is usually Sonoma since its the closest area to the city. We stopped in the adorable town of Healdsburg in the Fall, while on our way to Mendocino and absolutely loved it — we made a mental note to visit for longer later in the year! This weekend, we headed up to Healdsburg early on Saturday and spent all day and night in the area. I have to say, I think Healdsburg is my current favorite Wine Country town!

Where we Stayed: 

We booked our trip just a few days before, and lucked out picking Harmon Guest House as our hotel. It’s right in the town square, so easily walkable to all the restaurants and tasting rooms. The hotel is new as of August 2018, and is the sister hotel to Hotel Healdsburg and H2 Hotel, both luxury hotels also located in the square. Harmon Guest House was perfect from the moment we walked in, and covered all the extra little details I always take notice of. Free snacks and waters in the room, delicious complimentary breakfast, and a turn down service with local chocolates. As guests at the hotel, you’re welcome to take advantage of the pool, or the pools and hot tubs located next door at the sister hotels. HGH offers complimentary bike use, has gorgeous, light-filled rooms, and large balconies – I wish we had planned to stay for more than just a night!

Where to Taste 

J Vineyards: Known for their bubbles, Pinots, and multiple classy tasting rooms on property. Try the Pinot Gris, I’m usually not a fan of this type of wine, and I bought a bottle! Perfect winery for a sunny day.

Martorana: All organic and low key tasting room with beautiful grounds. The perfect place for a lunchtime stop. Bring a picnic and snack while tasting the wines and olive oils, especially the Zinfandels! My favorite stop of the day.

Trattore Farms: If you’re there for the views, this is the place! The wines weren’t especially notable to me, but the patio overlooking all of Dry Creek Valley and the curated shop filled with wine country specialties, made this a special stop.

David Coffaro Winery: I think everyone is given the VIP experience here. We were able to taste wine right out of the barrels and had a very interactive experience. We bought a bottle of their outstanding Zinfandel.

Outfit Details: J. Crew Jumpsuit / Similar Wicker Purse

Where to Eat & Drink 

Healdsburg’s restaurant scene is popping! The locals in the area that we chatted with mentioned this to us multiple times. What was once a lesser known town in Sonoma County, has turned into quite the hot spot. In my opinion, this little square has the best dining choices when it compares to the other town squares in the area. I’d like to spend a week eating (and drinking) my way through charming Healdsburg. (Note: The once popular Shed has now closed. This was a huge draw to Healdsburg for us in the past so I wanted to mention just incase you’re heading there to check it out.) 

Chalkboard: I loved everything about Chalkboard. Their menu is designed to be shared, which is ideal since I hate having to choose one thing at a restaurant. We had the pretzel with cheese, fried brussels sprouts, mushroom grass fed butter pasta, salmon carpaccio (on special), and chocolate bread pudding. The service level was also outstanding – we can’t wait to come back!

Barndiva: This place came highly recommended to us and it did not disappoint! The perfect place to stop in between tastings for an indulgent lunch. I loved their brie and veggie omelette. Don’t get me started on the addicting fries…

Flying Goat Coffee: They have the ultra-rare Oatly Oatmilk, which of course I had to get! We spent our morning here over lattes planning out our day of tastings.

Duke’s Spirited Cocktails: The best Moscow Mule and the perfect break from vino.

Harmon Guest House Rooftop: Gorgeous views and atmosphere with a sophisticated cocktail list.

Spoonbar: Breakfast here came with our hotel stay, but the restaurant is open to the public, and the breakfast was one of the best I’ve had in awhile. Don’t forget to add a mimosa!