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Credit: Christian Horan, Montage Healdsburg
Credit: Christian Horan, Montage Healdsburg

How to Spend a Weekend in Healdsburg—California Wine Country’s Hidden Gem

Farm-to-Table Cuisine, Beautiful Wineries and a Lavish New Hotel Are Just an Hour Flight Away

The charming destination of Healdsburg offers a serene escape filled with premier wine and farm-to-table cuisine. Located in the heart of Sonoma County, about 45 miles north of San Francisco, this small town is ideal for a weekend filled with relaxation. There’s fewer crowds compared to destinations like Napa and Sonoma Valley, and while there may be an “off season” in cooler months, there’s really never a bad time to visit Northern California (especially if it involves drinking wine). Healdsburg Itinerary

Hop on a direct, one-hour flight from SNA or LAX to STS for a seamless travel experience. Even if you have only two days, a trip to Healdsburg is well worth it. This is your 48-hour itinerary for a weekend in wine country’s hidden gem, Healdsburg. 


Where to Stay

Montage Healdsburg

Stay at the recently opened Montage Healdsburg, situated on rolling vineyards and filled with luxurious amenities (like the zero-edge resort pool and 11,500-square-foot spa). If there’s ever been a hotel to splurge on, this is the one. From the moment you arrive, the service is impeccable. After you’ve been escorted to your room via golf cart, sit out on the private patio with a glass of wine in hand, taking in the peaceful sounds of nature. Between the bathtub, outdoor shower and firepit, you’ll be in total relaxation mode before heading down to Hazel Hill for a decadent dinner. French-inspired, California cuisine made with locally sourced ingredients awaits—go for the chef’s special of the day!

Healdsburg Itinerary

Hotel Trio

For a more affordable hotel option, Hotel Trio is located closer to downtown Healdsburg. There’s a complimentary shuttle that can take you directly into town, and bikes are also available for cruising around town. Plus, check out Rosé Robot—yes, a literal robot—that will bring rosé to your hotel room door. 



Wineries to Visit 

Jordan Vineyard and Winery

Jordan Vineyard and Winery
Credit: Jordan Vineyard and Winery

Closest to Montage Healdsburg (they actually share some property), Jordan Vineyard and Winery offers French-inspired wine at their enchanting estate. Choose between a vineyard or seated tasting as you learn about the wine-making process and the history of Jordan Vineyard and Winery.

Local Insight: This year, the winery is celebrating 50 years with a variety of special events and happenings!

Healdsburg Itinerary

Marine Layer Wines

Marine Layer Wines, located in downtown Healdsburg, is one of the most aesthetically pleasing tasting rooms, thanks to local design team Hommeboys. This small-production winery focuses on cool-climate wines. Pop in before dinner for a glass and a light snack by the fireplace—they’ve partnered with nearby restaurant Little Saint to offer a stellar selection of small plates (the plant-based mezze plate is a must). 

The Harris Gallery Art & Wine Collection

Different from your everyday wine tasting, The Harris Gallery offers a chance to walk around a beautiful fine-art gallery located in a historic Healdsburg building built in 1908. Since then, there’s been some renovations, but bits and pieces are reminiscent of the original. All of the art found inside is by the talented father-son duo M.C. Harris and A3L3XZAND3R. Sip a tasting flight in the outdoor cabins or browse the gallery with a glass in hand. No, you don’t need a reservation!

If time permits, Dry Creek Vineyard and Seghesio Family Vineyards are well worth checking out. Map out your plan beforehand to maximize time at each stop. Visiting three wineries a day in Healdsburg will be plenty!



Where to Eat 

Credit: Barndiva
Matheson’s Roof 106

The culinary scene in Healdsburg has an overall emphasis on farm-fresh, locally sourced cuisine. Expect exquisite flavors and unique dishes from each restaurant. Dine in a barn at Barndiva, which earned a Michelin star in 2021; go for the goat cheese croquettes, beet and coffee risotto and the duck breast. Lounge at Matheson’s Roof 106 while snacking on the spiced delicata squash and Rancho Gordon white bean hummus plate. Spend an hour or two walking around the Healdsburg Plaza throughout the day, stopping in different boutiques and grabbing an ice cream from Noble Folk.


Healdsburg Itinerary

Healdsburg is full of passion—passion for food, wine and community. Even in competing industries, the local residents support one another to create such an idyllic community, even for visitors. Whether it’s for a romantic weekend, a girls’ trip or even a solo few days away, head to Healdsburg for your next California escape.

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Taylor is a graduate from the University of Southern California with a degree in journalism. She is our Los Angeles and Orange County editor. You can find her dining at a new restaurant, in the ocean or planning her next adventure. Say hello!

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