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Imagine rolling hills, vineyards flashing by on a slow drive, and that quintessential countryside smell — welcome to Healdsburg, California.

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Healdsburg is one of those places in Sonoma County that makes a name for itself in culinary and wine experiences due in large to one reason: the true integration of farm to table. You know in 2014 when you started paying for menus titled “farm to table”? Well, Healdsburg has been doing this for fifteen years plus (they kindly say you’re welcome). This unique ability to bring fresh produce right from their backyard into different and exquisite experiences changes the way you look at even the simplest ingredients.

The wineries are changing the game when it comes to how you encounter their wines. Taking a stop at the iconic Jordan Winery for the Estate Tour & Tasting allows you to explore the estate grounds and learn about how the farm and winemaking process coexist and amplify one another. At the end, you then taste a curated selection of food delicacies paired with their wines — all from their backyard, which you just saw. I can’t think of anywhere else you can do this?

Head down to Healdsburg Square and see why most people spend their afternoons strolling around from one dining spot to another. Spend countless hours in SHED, shop their craft goods, and leave with a coffee in hand. From here, you can meander through the endless boutiques in the square and even end the day for a late tasting at the Portalupi Tasting Room (Hint: they’re open later than everyone else 11am – 7pm).

Sarah Gerber of Twenty Twenty Studios and I, set out to immerse ourselves in this well-talked about town with one mission in mind: the best experience in food and wine. We sought high and low, in every corner, and craved to narrow Healdsburg down to the highlights. We asked the “locals” where they would be on a Saturday, and got some great pointers. Most people come for the weekend only having enough time for a few wine tastings and meals, so decisions can either be fortunate or fatal. So, if you’re going to go, why not experience the best?

The Local’s Weekend: A Healdsburg Guide

How to get there

  • Only a short hour-and-a-half drive from San Francisco (without traffic, 2 hours with), Healdsburg is quite easy to get to. If you are flying from out of town, flying into San Francisco or Oakland would be your airports of choice. A car is needed to get around, so be sure to rent one.

Where to stay

  • Hotel Healdsburg: Modern luxury meets sleek appointed rooms. Based right in the heart of Healdsburg Square, the Hotel Healdsburg binds the spa atmosphere with a culinary emphasis. With a pool in the back of the hotel, it will be your go-to spot when you need to beat the heat.
  • Hotel Les Mars: It is only natural that Relais & Chateaux would have a stamp in this adorable town, and they’ve done it well. Think old world charm meets a French maison in the countryside. Only one block away from the main square, one could easily walk to most of the restaurants nearby.
  • H2 Hotel: This boutique, eco-minded hotel lies just near the Healdsburg Square. Think young, playful, and creative spaces waiting for you to dive into.

Where to eat

  • SHED Cafe: I walked in for breakfast, and somehow managed to stay through until lunch — this place will do that to you. Coffee bar, pastry shop, to-go counter, fresh produce grocery store, kitchen & home store, and a cafe all under one creative roof. Let’s just talk about the cafe, lunch or breakfast, the food is centered around fresh local ingredients crafted in a way that captures your attention with every bite. Some of the must try plates are the Mezze plate, the Spring Peas, and the Cilantro Cured Black Cod. Their seasonal Shims are a definite need to try — it spruces up your dining experience.
  • Chalkboard: If you have one dinner in Healdsburg, be sure to book your table at Chalkboard. You may of came for the small plates like the iconic Warm Pretzels or Pork Belly Biscuits, but what you need to also try is the pasta. Made in house, changed weekly, and invented with local ingredients, the pasta hits it out of the park — the Pasta Tasting is a highlight and one to remember. Though you ought to save a little room for dessert, like the Candy Bar or their Panna Cotta.
  • Barndiva: Playful creations focused on eating what you see, a restaurant, cocktail lounge, and a wine bar all in one. Menu highlights include Yellowfin Tuna, Crispy Duck Confit, and Lobster Risotto.
  • Flying Goat Coffee: In the heart of Healdsburg Square, a modern coffee shop awaits for your daily caffeine indulgence.
  • Noble Folk Ice Cream & Pie Bar: You know when you try something you go back to it twice in less then 24 hours? Yes, I did. Inventive ice cream flavors, topped with dehydrated raspberries, edible flowers and more. Not to mention they have a pie bar!

Where to wine taste

  • Jordan Winery: The winery that tops the list as the full experience, think winery meets culinary experience — all placed in a romantic French château. You can’t do every wine tasting in the valley, so stick to a few and place your name on a reservation for the Estate Tour & Tasting. Jordan Winery will sweep you off your feet with stunning views and the friendliest of hosts.
  • J Vineyards & Winery: Did someone say bubbles? Whether you fancy a brut, a brut rosé, or a cuvée, you can try them all in one tasting at J Winery. Sit out on the patio, enjoy the J Sparkling Legacy Flight and add on the Cheese & Charcuterie pairing for a relaxed afternoon.
  • Portalupi Wine: In the heart of Healdsburg Square, this boutique winery has a quaint tasting room where you can indulge in their Italian inspired wines. The 2013 Barbera is a highlight and the one to bring home for a second taste (though you may end up bringing many more of their Zinfandels and Pinots home with you). In the back part of the tasting room, they’ve opened a space where they will be hosting different experiences for guest to join in on.

What to experience

  • SHED: I talked about the food, now let’s talk about the experience at SHED. Curated goods, for both home and kitchen, the shopping experience is to die for. Another part of the SHED experience is the Grange — a space for gathering together to do classes centered around food and farming. If you are around for one of these classes, it’s a great add on to your time in Healdsburg.
  • Russian River Adventures: Float down the Russian River on a leisure weekend or mid-week day, taking in the countryside. Full-day or half-day adventures await on these self guided eco-adventures.
  • Akoia Day Spa: Take off your shoes, kick back and relax with a spa treatment at Akoia.

Find more to do in Sonoma County on their extensive website here.

All photos taken by the talented Sarah Gerber from Twenty Twenty Studios

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*Bon Traveler & Twenty Twenty Studios were guests of many of the vendors. As always, all opinions are our own.

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