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Healdsburg travel guide: three-day itinerary for wine lovers

If you're planning a trip to Sonoma wine country, get your winery visits and restaurant bookings lined up in advance. To help you plan your holiday, Jess Lander provides the perfect three-day itinerary for a wine lover in Healdsburg...

This Healdsburg travel guide is the next installment in Jess Lander’s Sonoma wine country tour.

Sonoma wine country is diverse and covers a large area. To help you plan a trip, we’ve divided the region up into three different itineraries, assuming a Thursday arrival, and have earmarked the best places to visit.

Look out for Jess’ Sonoma travel itinerary, and her West County & Sonoma Coast itineraries coming soon

Healdsburg travel guide

Healdsburg, Credit sonomacounty.com


Why go?

The darling of Sonoma County, Healdsburg is equal parts small town charm and lap of luxury. A 90-minute drive from San Francisco, it’s also the perfect jumping off point to explore three of Sonoma County’s most revered AVAs: Russian River (known for Pinot Noir and Chardonnay), Alexander Valley (known for Cabernet Sauvignon that can compete with Napa), and Dry Creek Valley (rooted in old vine Zinfandel).


Check into the Montage, Sonoma’s newest hotel and arguably one of the top resorts in America. Although just a few minutes from the centre of town, the Montage sits on 258 acres and feels completely removed from urban life.

Stay in a luxury, modern day treehouse with vineyard and mountain views, lounge by one of two pools, and then dine on the terrace at the Montage’s incredible Hazel Hill restaurant.


Accommodation at the Montage hotel, credit www.montagehotels.com



Start the day at the Healdsburg Plaza which, similar to the Sonoma Plaza, is lined with shops, wine tasting rooms, restaurants and bars. Grab a light pastry breakfast at Quail & Condor, a new bakery from local celebrity Melissa Yanc, the winner of the 2019 Food Network Holiday Baking Championship. If you’re up early enough, snag the first appointment of the day at Siduri Wines for an in-depth exploration into single-vineyard California Pinot Noir.


Reserve the Paris on the Terrace experience at Jordan Vineyard & Winery in Alexander Valley. This classic, ivy-covered French chateau makes just two wines — a Cabernet Sauvignon and Chardonnay — but you’ll get to sample both, in addition to a pour of Champagne and a special library vintage throughout this leisurely, multi-course lunch at a private bistro table.


Spend the afternoon outside enjoying the beauty of the Russian River, where you can rent kayaks, canoes, rafts and stand-up paddleboards from several local companies, or simply take a dip and relax on its shores. Alternatively, rent a bike from Getaway Adventures and discover Healdsbug’s stunning country backroads (an electric bike will help you get up and over the rolling hills).


Get dinner at The Matheson, a new, three-story, farm-to-table restaurant and sushi bar, complete with a rooftop cocktail lounge, on the Healdsburg Plaza. Locally-beloved chef Dustin Valette’s family’s restaurant Valette is a Healdsburg staple and The Matheson is located on the very same site his great-grandfather’s bakery once stood.

If you’re looking to continue the evening, head to new bar Burdock, also on the plaza, for Havana-inspired cocktails.

Jordan Winery

Paris on the Terrace Experience at Jordan Winery, credit www.jordanwinery.com



Grab coffee and a light breakfast from Costeaux French Bakery, which dates back to 1923. The deep-dish quiche is legendary.


Drive roughly 15 minutes out to Flowers Winery in the Russian River Valley and book the Bottles & Provisions experience ($75 per person), featuring a half bottle of wine per guest and a picnic basket of culinary delights enjoyed within a breezy garden cabana. Flowers pioneered growing Pinot Noir and Chardonnay on the rugged and harsh-weathered Sonoma Coast 30 years ago and this relatively-new Russian River estate has made their beautiful wines accessible to visitors for the first time.


Pass back through the centre of Healdsburg and then out to Dry Creek Valley, the third wine country region that envelops the town. Less than 20 minutes from Flowers and then up a narrow, one-lane road is the undeniably hip Reeve Wines, set amongst oak trees in the most rustic, quiet, and relaxing country setting. Enjoy an oh-so casual tasting of Reeve’s wines, which always sell out, ranging from Pinot Noir and Chardonnay to Syrah, Cabernet Sauvignon, and even Riesling. If you’re lucky, the pizza oven will be firing.


While in Healdsburg, it’s worth the splurge (a tab for two can easily reach $1,000) to dine at SingleThread, a three Michelin-starred restaurant that’s like Sonoma’s version of the French Laundry — except the dishes featured on the 11-course tasting menu are lighter, fresher, and more contemporary-driven with a Japanese influence. Tables for the following month are released on the first of every month at 9am and often sell out, so you’ll want to be at the ready.

Single Thread Farm

The farm at Single Thread Restaurant, credit www.singlethreadfarms.com


Chances are you’ll still be full from SingleThread, but if you’re up for brunch before leaving Healdsburg, Barndiva, one of the original farm-to-fork restaurants in town, is the place to go with bistro garden seating and items like Dungeness crab Benedict and black truffle Croque Madame on the menu.

If you have time for one more wine tasting, head to the new Bacchus Landing wine tasting collective, located just outside the edge of downtown Healdsburg and home to eight small, local wineries.

Barndiva Restaurant

Barndiva Restaurant, credit www.barndiva.com

Related content:

Sonoma travel guide: the perfect three-day itinerary

Best wine bars in Napa and Sonoma

California Syrah: top Sonoma County wines

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