Ultimate Healdsburg Travel Guide: Plan Your Perfect California Trip

Healdsburg could fairly be described as the jewel of California Wine Country. It’s a special highlight of Sonoma County, which was one of iBestTravel’s 50 Best Places to Travel in 2021. “It’s a charming little town where you can eat incredible pastries on a park bench under redwoods in the morning, taste wine and spirits at the source, grab an organic burger or wood-fired pizza for lunch on a patio, detox with a shrub or tea tasting in the afternoon, and dine on three-Michelin–star cuisine at night before walking back to your hotel — all without getting in a car,” says Sonoma County denizen of 20 years and Healdsburg expert Lisa Mattson, author of “The Exes In My Glass: How I Refined My Taste in Men & Alcohol” and food and wine contributor for Wine Country Table.

It’s the only town in wine country that sits at the epicenter of three different wine regions — Russian River Valley, Dry Creek Valley, and Alexander Valley — each with unique climates and grape varietals, Mattson adds. The distinctive year-round destination with just over 11,000 residents is a true epicurean hotspot with an extremely charming town square, around which some of its best hotels, restaurants, and shops sit, not to mention approximately 40 tasting rooms. “The culinary scene has the kind of diversity you find in a big city, but it’s all centered around this quaint town’s park-like plaza,” says Mattson, and includes “Valette, the poster child for what a local wine country restaurant should be.”

In the miles just beyond, there are around 80 vineyards, including renowned labels Flowers, Jordan Winery, and Silver Oak. Beyond that, the natural beauty is spectacular and begs visitors to get outside to enjoy hiking, biking, and horseback riding. In Healdsburg, it truly seems there’s something for every taste and type.

Best Hotels & Resorts

Montage Healdsburg

Located eight minutes outside of town, this resort nestled among acres of grapevines epitomizes bucolic wine country from its beekeeping experiences to its farm-fresh Hazel Hill restaurant. The five-star Montage Healdsburg is acclaimed for luxurious accommodations and ranks No. 10 among the World’s Best Resorts in California.

Harmon Guest House

This hotel, named for Healdsburg’s founder, provides an artistic and hip atmosphere. Its 39 spacious rooms, along with an outdoor swimming pool, combine local art and furnishings, establishing a unique experience.

H2 Hotel

Upon arrival, you’ll find a hip eco-hotel featuring one of the coolest bars in town. Spoonbar, the principal dining destination, spills onto the sidewalk and grass area of this boutique hotel adorned with succulents under a wavy roof, making it a vibrant spot.

Hotel Healdsburg

Fantastically located at one corner of the central plaza, Hotel Healdsburg, opened in 2001, is referred to as the grande dame of downtown. The luxurious hotel, with a lobby lounge that gathers visitors and locals for live music and drinks, features modern minimalist rooms, a sunny swimming pool, and Chef Charlie Palmer’s Dry Creek Kitchen.

The Madrona Hotel

This 1881 estate underwent a reimagining in 2022, blending quirky, luxurious decor with its rich past. The Madrona is recognized on lists for Best New Hotels and Readers’ Favorite Hotels in the World. Guests are encouraged to enjoy a relaxing Sunday afternoon on the porch with delightful appetizers.

Best Things to Do

Taste wines at vineyards and tasting rooms

Start your wine journey at remarkable spots like Jordan Winery, Silver Oak, and Flowers — all respected producers with beautiful grounds and remarkable tasting experiences. There are limitless places to sample wines in Healdsburg, including beloved varietals like pinot noir, chardonnay, cabernet sauvignon, and zinfandel. Other excellent stops include Reeve, Hawkes, Amista, and tasting rooms right in the plaza, such as Marine Layer and Idlewild.

Take a hike

With gorgeous weather nearly year-round, especially in the presence of redwoods, forests, and rivers, Healdsburg is ideal for outdoor exploration. The Healdsburg Ridge Open Space Preserve is perfect for solo hiking and forest bathing. Several wineries offer guided hiking tours, and biking tours are also a fantastic option available with local operators, such as Getaway Adventures.

Try a craft class

Winemaking isn’t the only creative pursuit happening in Healdsburg. Visitors can engage in various craft classes, such as block printing and Japanese sashiko mending. One unique offering includes a 19th-century North American art form called punch needle at Crafted at Appellation, where classes are paired with premium wine and delicious bites from local chefs.

Practice yoga among grape vines

Experience yoga in a breathtaking setting amidst lush vineyards. Properties like Bricoleur Vineyards offer Sunday Yoga in the Vineyards, while Amista Vineyards offers a session followed by a glass of estate-grown bubbly, blending relaxation with the allure of wine country.

Stop by a pop-up for dinner

Discover culinary creativity at pop-up establishments throughout this gastronomic town. Notably, Le Dîner is Troubadour Bread & Bistro’s popular French-inspired spot, beckoning visitors, while Second Staff organizes pop-up dinners at Marine Layer Wines’ chic tasting room, serving delicious small plates infused with Michelin-worthy elements.

Best Restaurants

SingleThread

Regarded as “the dining experience of a lifetime,” this three-Michelin-starred establishment also serves as a five-room luxury inn and regenerative farm. The culinary efforts of husband-chef and wife-farmer duo Kyle and Katina Connaughton create unforgettable dishes that justify the lengthy reservation waitlist.

The Matheson + Valette

Chef/owner Dustin Valette has earned admiration for his contributions to Healdsburg’s culinary scene, as celebrated in The Matheson’s two-in-one spot. Diners can enjoy a micro-seasonal, hyper-local menu along with an impressive selection of 88 wines, coupled with vibrant rooftop dining.

Barndiva

Known for its Michelin-starred cuisine, Barndiva offers farm-to-fork dishes in a modern, vibrant atmosphere. The garden setting adds to the charm, along with creative non-alcoholic options such as the Belly Rub Shrub, designed for those seeking refreshing alternatives.

Little Saint + Second Story

Recognized as Healdsburg’s premier vegan eatery, Little Saint introduces a shrub bar focusing on low-alcohol and no-alcohol drinks, fulfilling a vital niche in the community. The newly opened Second Story, helmed by Executive Chef Stu Stalker, offers upscale vegan dining for culinary enthusiasts.

Bravas Bar de Tapas

This beloved local tapas bar combines a cozy indoor-outdoor atmosphere with a menu that showcases authentic Spanish paella. Chef/owners Mark and Terri Stark captivate diners with their genuine approach to Iberian cuisine.

Best Time to Visit

May through August is considered the quintessential time to visit Healdsburg, highlighted by weekly summer concerts and the Healdsburg Jazz Festival in June. Visitors can expect warm, dry days with cooler nights, resulting in delightful temperature swings. Mattson suggests the shoulder months of April and November for a less crowded experience, while March offers a stunning display of wild yellow blooms as spring introduces itself. Additionally, festivities like Barndiva’s Fête Blanc and Fête Rouge provide unique opportunities throughout the year, with quiet winter months conducive to warm indoor experiences at tasting rooms and cafes.

How to Get There

Healdsburg is a scenic 75-minute drive from San Francisco, though weekend congestion should be considered as many Northern Californians head to wine country. For those flying, consider landing at either San Francisco International Airport (SFO) or Oakland International Airport (OAK) and renting a car. Alternatively, flying directly to Charles M. Schultz Sonoma County Airport (STS) is an excellent choice, as it’s only 15 minutes south of Healdsburg and provides convenient rental car options.

How to Get Around

While Healdsburg is incredibly walkable, visiting wineries mandates transportation. Ride-shares may not always be reliable due to limited drivers. Therefore, consider using a rental car with a designated driver or engaging a local driver service that can enhance your wine country experience.