Crafting the Ideal Itinerary for Healdsburg, California

Healdsburg is truly a gem nestled in California's Wine Country, prominently featured in Sonoma County, recognized by T+L’s 50 Best Places to Travel in 2021. According to Lisa Mattson, a longtime local and author of “The Exes In My Glass: How I Refined My Taste in Men & Alcohol,” this quaint town offers a unique experience: enjoy delightful pastries on a park bench beneath redwoods in the morning, savor wine and spirits where they're made, indulge in an organic burger or wood-fired pizza for lunch on a patio, refresh with a shrub or tea tasting in the afternoon, and relish exquisite three-Michelin-star cuisine at night—all without needing to drive.

This charming town uniquely lies at the heart of three renowned wine regions—Russian River Valley, Dry Creek Valley, and Alexander Valley—each boasting its own climate and grape varieties, as noted by Mattson. With a population just over 11,000, Healdsburg stands out as a culinary destination with a picturesque town square that hosts some of its finest hotels, eateries, and shops, along with around 40 tasting rooms. Mattson highlights the diverse culinary scene reminiscent of a big city, centered around the town’s park-like plaza, featuring gems like “Valette, the epitome of a local wine country restaurant.”

Just beyond lies approximately 80 vineyards, featuring esteemed labels like Flowers, Jordan Winery, and Silver Oak. The surrounding natural beauty is breathtaking, inviting visitors to partake in hiking, biking, and horseback riding. In Healdsburg, there truly is something for everyone to enjoy.

Top Hotels & Resorts 

Montage Healdsburg  

Just eight minutes from downtown, this resort set among sprawling vineyards embodies the charm of wine country, featuring beekeeping activities and the farm-to-table Hazel Hill restaurant. Its luxurious rooms and suites boast floor-to-ceiling windows, perfect for soaking in the scenery. The five-star Montage Healdsburg was honored as No. 10 in T+L’s World’s Best Resorts in California of 2023.

Harmon Guest House 

For stunning sunsets, there’s no better spot than the rooftop of this hotel, named after Healdsburg’s founder. Mattson describes it as “artistic and hip.” With 39 spacious rooms, this community-focused property features an outdoor pool and is adorned with locally sourced art and furnishings.

H2 Hotel 

Mattson says, “When a trendy eco-hotel boasts one of the coolest bars in town and is situated right across from the other top two bars, you know you’ve found the perfect spot.” Spoonbar, the vibrant dining and drinking venue, seamlessly connects to the sidewalk and green space of this 36-room boutique hotel, adorned with succulents beneath a wavy roof.

Hotel Healdsburg 

Ideally situated at one corner of the central plaza, Hotel Healdsburg, which opened its doors in 2001, is referred to by Mattson as “the grande dame of downtown, even if it’s not particularly large.” It introduced a level of luxury to this wine-centric town before it gained widespread fame, and its lobby lounge, Spirit Bar, is a popular spot for both visitors and locals to enjoy live music and drinks. (“The happy hour menu is one of the best-kept secrets in town,” says Mattson.) The hotel features 55 modern, minimalist rooms, a sunny swimming pool, a collection of bicycles, and Chef Charlie Palmer's Dry Creek Kitchen, all exuding a quintessentially Californian vibe.

The Madrona Hotel 

Originally built in 1881, this estate was reimagined in 2022 by co-owner and interior designer Jay Jeffers, showcasing a playful mix of antiques and luxurious, colorful elements. Subsequently, The Madrona was featured in Dinogo’s lists of the Best New Hotels and the Readers’ Favorite Hotels in the World in 202. Mattson recommends that guests of the 24 stylish rooms and suites “enhance your day-drinking experience with a Sunday afternoon on the porch of this beautifully restored Victorian. The caviar and chips appetizer isn’t unlimited, but you’ll certainly wish it was.”

Top Activities to Experience 

Sample wines at vineyards and tasting rooms.

“I always bring my out-of-town guests to these three wineries, and they are consistently amazed,” says Mattson of Jordan Winery, Silver Oak, and Flowers—all esteemed producers boasting stunning grounds and top-notch experiences. Healdsburg offers countless venues for wine tasting, featuring varieties like pinot noir, chardonnay, cabernet sauvignon, and zinfandel. Other must-visit spots include Reeve, Hawkes, Amista, as well as Marine Layer and Idlewild right in the plaza.  

Go for a hike. 

With stunning weather almost all year round, along with redwoods, forests, and rivers, Healdsburg is an idyllic spot for outdoor enthusiasts. The Healdsburg Ridge Open Space Preserve is perfect for solo hikes and forest bathing. Some wineries provide guided experiences: Bella Winery offers Hike the Hill tours led by a local naturalist and nutritionist; Jordan’s 1,200-acre preserve occasionally hosts vineyard hikes; and Amista’s Morningsong Vineyard features a half-mile walking trail. Alternatively, explore on two wheels with Getaway Adventures’ Healdsburg bike and wine tours.  

Join a craft class. 

Healdsburg isn’t just about winemaking; it’s also a hub for creativity. Visitors can learn skills like block printing, moss wall art, and Japanese sashiko mending. There’s even a 19th-century North American art form known as punch needle, which curious minds can explore at Crafted at Appellation. Here, classes taught by local designers come with premium wine and delectable bites (after all, Chef Charlie Palmer is a co-founder). It’s a much more engaging experience than traditional sip-and-paint sessions. 

Enjoy yoga among the grapevines. 

Indoor yoga classes will never be the same after practicing downward dog and warrior poses surrounded by lush green vineyards. Several venues, like the picturesque Bricoleur Vineyards, host Sunday Yoga in the Vineyards, providing classes in a true wine-lover’s paradise. Amista Vineyards even follows its one-hour session with a glass of their estate-grown bubbly. 

Visit a pop-up for dinner. 

In this culinary haven, pop-up restaurants and dinners are always happening, and Mattson highly recommends two specific options. Le Dîner is the trendy French-inspired evening spot at Troubadour Bread & Bistro. Meanwhile, Second Staff hosts pop-up dinners at the incredibly cool Marine Layer Wines tasting room after hours. “The chefs offer small plates with Michelin-quality flair but without the pretense,” notes Mattson. 

Top Restaurants 

SingleThread  

Described by Mattson as “the dining experience of a lifetime,” this three-Michelin-starred, 52-seat restaurant also features a luxury inn and a regenerative farm. Culinary power couple Kyle and Katina Connaughton work their magic in the kitchen, creating dishes that fully justify the lengthy waitlist for reservations. 

The Matheson + Valette 

“Everyone adores Dustin Valette, our local star who became a top chef and returned to showcase his skills,” says Mattson about The Matheson’s chef/owner. He opened this dual-concept restaurant in 2021, following the success of Valette, just across the plaza. (There, “Dustin’s portions and hospitality are as generous as his personality,” notes Mattson.) The menu features micro-seasonal, hyper-local dishes, and downstairs offers 88 wines by the taste or glass, while Roof 106 serves up favorites like fried sweet corn, marinated olives, and pork belly pizza, which Mattson says are always a must-try. 

Barndiva 

“A vibe not to be missed,” is how Mattson describes one of her personal favorites for its Michelin-starred farm-to-table cuisine, which she characterizes as “fresh, modern, elevated, and distinctly Barndiva.” The restaurant also boasts a lovely garden ambiance and an impressive selection of non-alcoholic beverages, including the Belly Rub Shrub, made with a turmeric spirit, turmeric-beet shrub, and ginger.  

Little Saint + Second Story

Healdsburg's hottest vegan spot, Little Saint, offers a “shrub bar and a focus on low-alcohol and non-alcoholic drinks [that] fills a void in our boozy bougie town,” according to Mattson. She is particularly thrilled about its new fine-dining sister restaurant upstairs, Second Story (also vegan), which launched in summer 2023 under Executive Chef Stu Stalker, who was previously with Copenhagen’s renowned Noma. 

Bravas Bar de Tapas

This beloved local gem offers year-round indoor and outdoor seating. “Our cherished tapas bar is nestled in an old Craftsman bungalow, serving sparkling wine in coupe glasses,” shares Mattson. Chef/owners Mark and Terri Stark are James Beard finalists with a special knack for authentic Spanish paella.

Best Time to Visit 

The ideal time to experience Healdsburg is from May to August, featuring the weekly Tuesdays in the Plaza summer concert series and the Healdsburg Jazz Festival in June. Visitors can anticipate hot, dry days and cool nights, with temperature variations of up to 30 degrees. Mattson personally prefers the shoulder months of April and November, “when it’s a bit less crowded.” However, she also enjoys March—marking the end of late winter’s mustard season when wild yellow blooms blanket the fields—along with Chef Charlie Palmer’s two-day Pigs & Pinot event at Hotel Healdsburg. Mattson highlights Barndiva’s Fête Blanc in August and Fête Rouge in November as fantastic celebrations, and she recommends food lovers and wine enthusiasts visit during the quieter, cooler months of January and February. “So what if it’s raining? You’ll be inside a tasting room, tea house, distillery, coffee shop, cafe, or restaurant anyway.” 

How to Get There 

Healdsburg is a picturesque 75-minute drive, covering 70 miles from San Francisco and the Bay Area. However, be cautious of weekend traffic as Northern Californians flock to wine country. For those traveling from elsewhere in the country or internationally, flying is the best option. You can either land at San Francisco International Airport (SFO) or Oakland International Airport (OAK), then rent a car for the 83-mile journey north — both airports are equidistant. Alternatively, you can fly directly to Charles M. Schultz Sonoma County Airport (STS), a lovely regional airport served by Alaska Airlines, American Airlines, and Avelo. It’s only 15 minutes and 10 miles south of Healdsburg and offers a Hertz rental car outlet as well as pickup areas for Lyft, Uber, and taxis. 

How to Get Around 

While Healdsburg is very pedestrian-friendly, not visiting any wineries would be a missed opportunity, which necessitates a car. Ride-sharing services are often unreliable due to a limited number of drivers. “You might get lucky with ride-share, but it's wise to plan ahead and be ready to wait,” advises Mattson. The safest option is to use your rental car with a designated driver or book a tour guide or driver service, both of which are plentiful in the area.