Have you ever picked up the New York Times, read about a place, and told yourself that one day you’ll go there? Do you really mean it? Do you cut it out and save it and show it to anybody who will listen? “Read this. Doesn’t this sound great?”

That’s Healdsburg. It didn’t happen right away. We read the article and two years or so later, we made it happen. We planned it quickly, just moments after lying in bed debating just how to pull off the perfect last minute spring break vacation.

There’s wine country. There’s Sonoma. And then there’s Healdsburg. Just about the most perfect small town you can find, with a plaza full of tall, lush trees with tasting rooms and restaurants galore. It sits nestled at the crossroads of Dry Creek, Alexander, and Russian River Valleys which means you’ve got endless amounts of wine and vineyards just a short drive in every direction.

Where We Stayed

We stayed at The Healdsburg Inn, a Four Sisters hotel located right on the plaza. It’s quaint and cozy and within walking distance to everything Healdsburg has to offer. Breakfast is cooked and served every morning and wine and cheese is offered every night at 5PM. Be sure to stop at the front desk and ask for two-for-one tasting coupons. The ladies at the front desk are extremely helpful and always willing to point you in the right direction. Cookies are available all day too!

Where We Ate

We arrived to Healdsburg early in the morning and since our rooms weren’t ready, we headed to Costeaux French Bakery for breakfast. Here is where Paul made the best decision of all of us, and the one I would most recommend for breakfast in Healdsburg. Don’t go for the $15 omelets like the Moms and I did. Just go for the Bloody Mary. For just $9, it’s a complete breakfast. And you see the spices around the glass? That’s not Old Bay. That’s Tajin, and it is amazing!

Healdsburg is well known for some restaurants that are a pretty big deal. Restaurants like Barndiva, Dry Creek Kitchen, Valette, and Chalkboard are just a few of the places listed at the top of “best restaurants in Healdsburg.” We didn’t get to these restaurants, mostly because when you are eating and sipping wine all day, small meals become your go-to thing. The places we did eat did not disappoint. Here are a few that we highly recommend:

If a fresh sandwich or salad is all you need midday, go to the Oakville Grocery, just steps away from the Healdsburg Inn. Everything is fresh and delicious here and the bread is outrageously good. Sit outside in the California sunshine and watch as people come and go through the plaza.

If brisket is your thing, head across the street to Kinsmoke. Paul and I stopped in here just to check the place out (we’d already had lunch). The staff was so friendly and when they heard that we weren’t eating, they gave us a taste of just what we were missing. With a sample of brisket in front of us, I couldn’t help but put together my own bbq sauce tasting. Paul and I differed on which ones we liked best, but it’s safe to say, you really can’t go wrong with any kind of bbq sauce. This place is definitely on our “must go back” list for whenever we find ourselves in Healdsburg again.

For the best happy hour in Healdsburg, head to Bravas Bar De Tapas. You’ll feel like you’re walking into someone’s home. Head straight out back and sit outside on the patio. Happy hour here is called Local’s 420 Hour since everything listed on the menu is $4.20. We highly recommend pulling up a seat at the bar for the bocadillo and the patatas bravas. Repeat after me, bocadillo.

If after a long day of vineyard hopping, a dozen oysters is more of what you’re looking for, head just across town to Willi’s Seafood and Raw Bar. Owned and operated by the same restaurant group as Bravas Bar De Tapas, Willi’s is serving up fresh oysters and seafood all day long. The service is friendly and the oysters are perfect.

Campo Fina is another great place for a snack or a full meal. Here you can play some bocce or spend your time at the bar snacking on tuna stuffed sweet n’ spicy peppers. I’m sure you can guess what I opted for. If you’ve gone too long without pizza, this is where you can also satisfy those bread, sauce, and cheese cravings. If you want our recommendation, go for the Pizza Anchovy. It’s divine.

You can’t go to wine country without having a picnic in a vineyard. And you can’t get your picnic from any other place than Big John’s Market. It may look like just any other grocery store when you pull in, but it’s just not. Order up a few sandwiches, grab some napkins and plastic utensils, and head to a vineyard that allows you to bring a picnic lunch. We had our Big John’s Market spread at Dry Creek Vineyards, which is a gorgeous setting for eating gorgeous sandwiches. Paul and I are still debating which vegetable sandwich was better: Oakville Grocery or Big John’s Market. We’ve settled on the fact that we just can’t say one was better than the other. They were both superb.

If there is one piece of advice that you take from this post, it should be this one. Just across the street from Oakville Grocery is a rather modern looking tasting room called Lioco. You should go there on a Tuesday at 4PM, right when they open. Why Tuesday, and why right when they open? Every Tuesday from 4-7, you will find Houtskool Dumplings, a pop-up dumpling shop serving little bundles of homemade love filled with vegetables, meat, and fish. They call them “artisan dumplings for everyday life” and they are just incredible. This is why you must arrive when they open. Other people know just how good they are too. Order them all with a bottle of wine for the best dumpling tasting of your life. By the way, the wine at Lioco is good too.

Tastings and Vineyards

Our first visit to a wine tasting room in Healdsburg was at Williamson Wines. The lady at the front desk of the Healdsburg Inn said this is the place to go since the emphasis is on food with wine. Since she was speaking my language, we headed straight to Williamson, where the owner sat us down and gave us a full education on Williamson’s wine and the food that goes best with it. We had such a good time here and enjoyed the experience so much that we became members. Rarely can we find a winery that ships to New Jersey, but Williamson can, since they don’t produce enough wine to use a distributor. You cannot buy Williamson in a store, but you can have it delivered straight to your door if you’re part of the club. The other perk to becoming a member of Williamson? Their recipe collection! On their website you can find a database of recipes created to pair with each of their wines. I am so eager to get our first shipment and start my own little culinary adventure, complete with wine pairing, right from my kitchen.

Aside from Dry Creek Vineyard, we also took a trip out to Ferrari-Carano Vineyards and Winery. This was my mother-in-law’s favorite stop of the whole trip. It wasn’t the wine that sold her, but the estate itself. With its beautiful gardens situated on a massive property filled with vines, this is what most picture wine country to look like. If you go here, make sure to walk downstairs and check out the barrel room.

Our Take on Healdsburg

We are simply head-over-heels in love with this little town. So much so, that Paul keeps giving me all of these reasons why we need to go back. I don’t know if I can completely trust him, or if he’s just looking for a way to get back to his late night ice cream spot, Noble Folk. Either way, I don’t need a reason to head back to Healdsburg. There are still so many restaurants that I haven’t had a chance to visit yet. Like any vacation for me, this was the “so much food, so little time” situation I always run into.

If you are headed to wine country, please, please, please remember it’s not all Napa. In fact, it’s so much more.

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