A Weekend Of Luxury In Healdsburg, California

Here's your 48 hour guide to a luxurious weekend getaway in Healdsburg, California! Wineries, hikes, delicious food and more awaits visitors!

One of the great things about not having traditional snowy winters is that you can enjoy the beauty of fall and temperate weather well past the holidays. If you’re a lover of fine dining, nature, wineries and laid-back luxury (who isn’t, right?) consider a road trip to Healdsburg, California.

As a lesser-known wine country destination than say, Napa Valley, its relatively uncrowded and offers an expansive selection of top-notch wineries, outdoor dining experiences, and unique ways to take in the beauty of the season. One great area for hiking, in particular, is Healdsburg’s Dry Creek Valley.

The view from the top of Lily Hill.

Located in Sonoma County, this viticultural area is a special place to explore and is best done so with a guided hike through vineyards, which includes exploring redwood groves and more. Though the fires ruined the grapes for winemaking, the silver lining is that the fruit still hangs from the vines. The hanging fruit on the vibrant fall colored leaves makes for a particularly stunning visual.

For those looking to travel (safely!) to the area, Hotel Healdsburg is offering a timely package that includes a two-night stay, daily breakfast, valet parking, and a privately guided hike through Lily Hill which starts off at Bella Winery located just 15 minutes away from the downtown area. Culminating in 360-degree views of the entire valley, this privately guided hike is just you and the guide (and maybe a significant other) so no need to worry about crowds.

Your guide takes you through beautiful trails along sections of the vineyards, pointing out interesting details of the terrain, history of the area, wildlife and more. As you make your way through the vineyards, the colors get more intense, the sun shines a little brighter and the entire valley brightens up. It’s a wonderful way to experience this area that most don’t get to experience.

Hiking in Bella Winery.

Once the round trip hike is over (about 1.5 hours depending on your fitness level), you arrive back at Bella Winery where you’re welcomed with a gourmet picnic lunch courtesy of Dry Creek Kitchen which includes Mary’s chicken salad; charcuterie and cheeses, baguettes, olives, a seasonal salad, pita chips and humus, cookies and more – enough for 4-5 people. The food is absolutely delicious and honestly couldn’t be more perfect for an upscale picnic!

Continue the experience with a wine tasting of Bella Creek’s wines ranging from Zinfandels to Chardonnays, depending on your taste preference.

The experience of sipping and eating on fine foods at the Lily Hill Estate is made even more special thanks to the peaceful atmosphere, looming olive trees, and the surrounding Dry Creek Valley scenery. It was here that Italian immigrant Adamo Micheli and his son, Angelo, planted the first vines over 100 years ago in 1915.

Healdsburg is home to plenty of outdoor activities as well including biking, hiking and running through areas that include Lake Sonoma, the stunning Armstrong Woods, Fitch Mountain or the Healdsburg Ridge. Not to mention, there are over 30 miles of river within Healdsburg alone so guests are encouraged to jump on the Russian River whether that be on paddleboards, kayaks, canoes or other means!

The front of Hotel Healdsburg in downtown Healdsburg.

Hotel Healdsburg is a great starting off point for any day excursion. Though navigating travel during this pandemic can be difficult, the concierge has created an easy-to-follow Outdoor Guide to the town and surrounding area, taking the pressure off you to plan your days. In addition to an outdoor guide, there are also a vast selection of wineries nearby should you want to wine your days away.

Popular wine destinations include the nearby Bricoleur Vineyards which has teamed up with Chef Shane McAnelly to create food pairings to accompany wine tastings; the picturesque Flowers Vineyards and Winery which has a special “Flowers + Florence” picnic offering that features Flowers wine and a signature fried chicken meal crafted by Tyler Florence; and Jordan Vineyard and Winery at their stunning Alexander Valley Estate and more.

For a particularly educational wine experience, book a 90-minute tour of Amista Vineyards, also located in Dry Creek Valley. During the walk and sip tour, you’re guided through their sprawling vineyards while hearing all about Amista’s sustainably-farmed grapes and taking stops to taste the wines.

You also get to explore the property’s Habitat Enhancement Project, which was built to sustain and restore the natural Steelhead trout and Coho salmon habitat in Dry Creek. The tour includes a bottle of estate wine to enjoy on the new, solar-powered patio, which you can enjoy with a delicious charcuterie plate as well!

In downtown Healdsburg are plenty of fantastic restaurants within close vicinity to the hotel. Located just opposite the historic town plaza, Pizzando is a lively restaurant with amazing wood-fired pizzas, seasonal antipasti; hand-crafted pastas and creative cocktails. Standouts include the calamari frito misto crispy lemon, artichoke, cauliflower, lemon aioli rigatoni alla Bolognese with house-ground lamb & beef, San Marzano tomato, garlic, basil, parmesan; mushroom & truffle oil pizza with mushroom cream, mozzarella, bacon, parmesan, truffle oil; and more.

Directly below the hotel is Charlie Palmer’s Dry Creek Kitchen with its progressive American cooking and extensive wine list of over 500 selections. The outdoor garden area is a perfect spot for outdoor dining under the shimmering string lights.

Nearby is Spoonbar known for its upscale, yet approachable American fare and “farm-to-bar” cocktails made with domestically produced spirits and organic herbs, fruits and vegetables grown by Sonoma County purveyors. The outdoor garden area is a charming place to dine on a variety of hearty, thoughtful dishes including Moroccan spice marinated chicken breast & thigh, couscous, almond, raisins, peas, chermoula sauce; maple leaf duck duo crispy breast, confit leg, huckleberry, glazed cippolini, creamy polenta; and 12oz 28-day dry-aged ribeye loaded baked potato, caramelized onions, crispy hobbs bacon, baby carrots and broccolini.

One more highly recommended restaurant is Valette, an upscale restaurant born from two brothers’ lifelong goal of creating an unparalleled dining establishment in their hometown of Healdsburg. The restaurant prides itself on perfectly marrying the best of the best from local farmers, winemakers and artisans to showcase their crafts in its innovative, tantalizing cuisine. Standouts include day boat scallops en croute with Jack Herron’s wild fennel pollen, American caviar and champagne beurre blanc; snake river New York steak with Mr. Duncan’s local mushrooms, celeriac mousseline, roasted bone marrow and fermented garlic butter; and the Szechuan crusted duck breast with liberty farms duck, poached quince, duck confit lumpia, forbidden rice and roasted bok choy.

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Chelsea is a San Francisco-based journalist whose passion revolves around exploring the world, immersing herself in foreign cultures, and of course, eating and drinking everything delicious.

Her work can be found in TravelPulse, Forbes, INSIDER, SF Gate and more. She covers all things food, drink and travel and is always up for an adventure, whether that means an adrenaline-pumping excursion or trying a new cuisine.


  1. January 12, 2021 / 9:19 am

    Chelsea. Great piece, probably your best ever! I have wanted to visit the wine country for awhile now and in fact, another couple has been asking my wife and i to plan a trip but did not know where to start. Would this be a good city to make as our base when we go or other places to consider? The only thing i wish was added to your post was a basic map showing location and relation to other cities, etc. But hey, i have looked it up. Again Chelsea, good job!! Keep up the great work and fingers crossed for s trip across the pond planned this Sept. Thanks.

    • Chelsea Davis
      January 12, 2021 / 2:37 pm

      Thanks so much Jim! Let me know if you need more recs!

    • Chelsea Davis
      January 12, 2021 / 2:58 pm

      Thanks so much! And that’s a great idea, will keep that in mind for my future posts! And in my opinion, it depends on what you’re both interested in. Napa Valley is another amazing wine country destination which I would start with first if you’re coming from that far away. It’s just bigger and has more of a dining, shopping and overall tourist scene. But Napa Valley is only an hour away from Healdsburg so it’s not too bad. And then San Francisco (my home town!) is about a little over an hour away from Napa. So none of it is too far out of reach. Does that help?

      • Jim cupp
        January 12, 2021 / 4:58 pm

        Thanks Chelsea, i did not realize they were so close to each other. In regard to our interest? Nothing exciting as we are getting old; sightseeing, drinking some wine and eating good food. You are a rock star Chelsea, thanks!

  2. Sonia Sparks
    January 13, 2021 / 8:00 pm

    Love the new blog, Chelsea! You are so kind and professional to work with. Your content is always thoughtful, on point, and accurate. Looking forward to reading more of your stories here!

    • Chelsea Davis
      January 15, 2021 / 3:31 pm

      Thanks so much Sonia!!! Always love working with you too!

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