Your Ideal Weekend Escape in Sonoma Wine Country

Sonoma County’s wine country has long been a beloved getaway for both Bay Area locals and visitors from Mytour. Boasting over 425 wineries and 18 AVAs, this expansive and diverse viticultural region invites countless weekends of discovery. Since the county is so large, the small town you select as your home base—whether it’s apple-loving Sebastopol, historic Sonoma, or riverside Guerneville—will shape your weekend experience.

Currently, one of the most vibrant towns to stay in is Healdsburg, which is enjoying a wave of new openings and renovations as fresh, locally owned businesses set up shop. This recent transformation makes it easier than ever to spend an entire weekend (or more) right in the town center.

Even if you’ve visited Healdsburg before, it’s worth a return trip. While many beloved spots remain, this small NorCal town is undergoing significant changes. Use this guide to help you navigate—from accommodations and activities to dining and drinking in this enchanting part of Sonoma wine country.

Where to Stay

A visit to Sonoma County invites a slower pace: enjoy long, leisurely breakfasts, pre-dinner lounging by the pool, and stargazing with a bottle of wine after the sun goes down. Our favorite accommodations in and around Healdsburg encourage you to unwind and relax.

Harmon Guest House

Harmon Guest House serves as a serene yet centrally located haven in the heart of Healdsburg. Each spacious and tranquil room features cozy reading nooks and small balconies, along with large, comfortable beds that guarantee a restful night. Guests are encouraged to relax outdoors, whether by the hotel’s solar-thermal heated pool or at the alfresco rooftop bar, aptly named the Rooftop. Dedicated to sustainability, the hotel has initiated several eco-friendly projects, including a rainwater harvesting system. Additionally, the hotel is involved in restoring the natural habitat along Foss Creek, which flows behind the property.

Montage Healdsburg

The 258-acre Montage Healdsburg opened in 2020, marking the debut of the first major resort in the Healdsburg region. However, ‘large’ here doesn’t equate to overwhelming. This tranquil, nature-rich retreat has beautifully integrated itself into its surroundings, featuring treehouse-style accommodations with spacious outdoor decks nestled among preserved oaks. The property’s restaurant, Hazel Hill, offers stunning views of rolling hills, making it an ideal spot for enjoying dinner and drinks at sunset.

The Madrona

Originally constructed in 1881 as a private home, The Madrona was transformed into Madrona Manor in 1981. After a change in ownership in 2020 and extensive renovations, it reopened in April 2022 as an eclectic, 24-room boutique hotel and social hub. With designer Jay Jeffers at the helm, the space has been creatively reimagined into a maximalist oasis, all while honoring the essence of the original building. New features include a resort-style pool and a bar and restaurant with a inviting patio, frequented by both guests and locals on warm evenings. Accommodations range from charming rooms in the main mansion to private bungalows nestled in a blooming garden.

Read our complete review of the Madrona.

The Lodge at Healdsburg

You have to love a wine country hotel where the reception area resembles a bar—and serves as one, too. Upon entering the Tuscan-inspired Lodge at Healdsburg, you’re greeted with a glass of local sparkling wine (or a local beer, if that’s your preference). It’s a welcoming gesture that confirms you’re in the right place. This 60-room boutique hotel was renovated and transitioned into a Hilton property, becoming part of the Tapestry Collection in 2023. The updated rooms are bright and elegant, featuring hardwood floors and gas fireplaces, overlooking a central courtyard that embodies a Tuscan ambiance with olive trees and terracotta tiles (along with two not-so-Italian hot tubs). During spring and summer, the property thrives with lush greenery. Bonus: The hotel is pet-friendly.

H2 Hotel

If you want to be right in the heart of Healdsburg, H2 is your spot. Even better: The 36-room hotel, which opened in 2018, stands as a stunning example of sustainable architecture. H2 is LEED Gold certified, with its striking green roof being one of the property's standout features. The hotel boasts an impressive array of other eco-friendly attributes, including occupancy sensors that control fans and air conditioning, furniture crafted from reclaimed wood, and solar panels that heat the pool and guest room water. H2’s design is impeccable, featuring bright, airy rooms with bamboo flooring, live-edge tables, elegant earthy hues, artwork by local artists, and glass carafes that can be filled from water stations on each floor. There’s plenty to enjoy, too: Grab a bike to explore town, dine at the on-site restaurant, Spoonbar, or join a partner activity like cycling with pro athlete Pete Stetina or gleaning with Farm to Pantry.

Where to eat

Kick off your day with coffee and breakfast at Black Oak Coffee in Healdsburg’s main square. The coffee is fresh, the staff is friendly, and the food is delicious, but this vibrant café is also dedicated to the community. The team donates 10 percent of their house espresso sales to charity and actively participates in local projects and fundraisers, such as supporting volunteers at the annual Russian River Watershed Cleanup.

Or make your way to Quail & Condor, a bakery created by SingleThread alums Melissa Yanc and Sean McGaughey. Known for their long-ferment croissants and handmade sourdough breads, you can’t go wrong with any selection. Recent highlights included parmesan and onion biscuits, black sesame calamansi cake, and an irresistible gluten-free cookie. Their merchandise, like sweatshirts featuring the phrase “weirdough,” is impressive, too.

For lunch with a view, visit Roof 106, a rooftop bar and restaurant that’s part of the Matheson, located in the former Snowflake Bakery space. Snowflake, founded by Honoré Valette, the great-grandfather of Matheson’s chef and owner, Dustin Valette, was aimed at keeping the community lively. While it’s renowned for its pizzas, be sure to try the Asian chicken salad with shaved cabbage and togarashi puffs. In the evenings, the downstairs transforms into a bustling fine dining venue, complete with a self-serve wine wall boasting an impressive array of vintages from around the globe, including hard-to-find selections like Opus One from Napa.

If you’re on the move, swing by Dry Creek General Store, a beloved deli and market on Dry Creek Road, for a quick sandwich between wine tastings. Alternatively, stock up on picnic supplies at the Italian market Ciao Bruto before heading out for the day.

For a pre-dinner cocktail, the vibrant garden-adjacent patio at the Madrona or the stunning sunset views at Hazel Hill are both fantastic choices. If you prefer to stay within the town center, settle in at the local favorite Lo & Behold for cocktails and fried chicken. All three venues offer a full dinner menu (Hazel Hill’s set tasting menu is particularly delightful) and are excellent for those craving more than just bar snacks.

Or visit Le Diner Troubadour, one of Healdsburg’s top sandwich spots—run by the creators of Quail & Condor—that transforms into an intimate 20-seat bistro at night. The seasonal menu is always a delight: expect dishes like mussels with onion and chervil, herb salad with black sesame and cultured cream, and pork with persimmon and nasturtium. Don’t miss the oat porridge sourdough (also available at the bakery), especially paired with their house-made butter—chef’s kiss.

For a more laid-back experience, visit Molti Amici, an Italian eatery exuding a charming Wes Anderson ambiance. From the gold lettering on the entrance to the green-and-white striped cushions and the mirrored bar adorned with a neon sign reading “many friends” (or “molti amici”), the atmosphere is both refined and welcoming. The menu delights with dishes like beet salad with labneh, handmade pastas such as gnocchetti with spring peas, and delicious wood-fired pizzas (the polpetta & pepperoni is a must-try). There’s even a bocce court on the back patio.

No dining guide to Healdsburg would be complete without mentioning SingleThread, a 52-seat gem boasting three Michelin stars and widespread acclaim since its 2016 opening. Chef Kyle Connaughton, who trained in Japan, merges ancient techniques with a hyper-local farm-to-table philosophy (many ingredients are sourced from the farm he runs with his wife, Katina) to craft an exquisite array of small plates. SingleThread also features a luxurious five-room inn above the restaurant—reserve both for an indulgent escape. Dinner reservations open on the first of the month prior and fill up rapidly.

Vegans (and even non-vegans) should check out Little Saint, launched by the SingleThread team in the former Shed building in April 2022. This versatile venue is perfect for any time of day, featuring a coffee shop, bar, market, and event space that hosts live music every Thursday (surprise performances from notable artists like Phoebe Bridgers are frequent). The real highlight is the tasting menu at Second Story, located on the building's second floor, offering lovely views of the treetops. Settle in for an evening of innovative vegan dishes like poached beets with marigold and hops, confit squash with chestnut, and potato terrine with preserved truffle. The menu evolves continuously, ensuring a creative and enlightening dining experience.

Wrap up your evening with a scoop or cone from Noble Folk Ice Cream, a beloved, LGBTQ+-friendly spot owned by Christian Sullberg and his partner Ozzy Jimenez, the former mayor of Healdsburg.

Where to drink

Healdsburg lies near two prominent AVAs: Dry Creek, celebrated for its zinfandels, and Russian River, famed for its pinot noirs and chardonnays. Exploring beyond the town is a must, but you could easily spend a weekend tasting right in Healdsburg. Begin at Bacchus Landing, a newly built Tuscan-style venue boasting five unique tasting rooms. Highlights include Setting Wines, a partnership among three friends that showcases some of the region's finest vineyards (you'll likely leave with at least one bottle of winemaker Jesse Katz’s cabernets), and Smith Story, operated by a husband-and-wife duo featuring grapes from Sonoma and Mendocino counties. Don’t forget to greet the winery's mascot, Lord Sandwich. In the bustling courtyard of Bacchus Landing, you can enjoy live music and indulge in wood-fired pizzas to keep you satisfied between tastings.

Continue your wine adventure at some of the newer tasting rooms in town. BloodRoot offers a trendy atmosphere with both an indoor space and a patio, serving high-quality, affordable wines crafted from grapes sourced throughout Sonoma County. While the sommeliers keep the exact origins of their grapes under wraps (a strategy that helps keep prices reasonable), you can trust their expertise. A few blocks away, Marine Layer invites guests to enjoy both a visual and sensory experience with wines from the Sonoma coast. In its fresh, youthful tasting room designed by L.A.-based firm Hommeboys, stylish visitors sip on delicately balanced, slightly briny pinot noirs while relaxing in yellow velvet chairs. Bonus: both places stay open until 7 p.m. (most tasting rooms close by 5 p.m.), perfect for a late-day glass of wine.

New to the tasting scene are the Society and Maison Wine Bar. The Society showcases wines from the Foley Family portfolio in a setting that feels reminiscent of an upscale wine club, complete with wood-paneled walls and a leather couch. Don’t miss their pairing options, which include everything from caviar and bubbles to chocolate and wine. For a more in-depth experience, spend an evening at Maison Wine Bar. It might be a bit hard to find on the main road, but once inside, owners and sommeliers Evan Hufford and Ryan Knowles will guide you through their favorite California wines, as well as beer and sake. It serves as both a wine bar (open until 2 a.m.!) and a retail shop, and they frequently host wine dinners in collaboration with groups like Second Staff.

To explore beyond the town of Healdsburg, begin with the Dry Creek AVA at Bella Vineyards, a family-owned winery that welcomes guests with its expansive grounds, featuring rows of old vines and towering redwoods. While a classic tasting on its olive tree-dotted lawn is tempting, we suggest trying one of the immersive tour options, such as the wine and hike experience or a unique vineyard tour in a decommissioned Swiss military vehicle, complete with a wine stop in a redwood grove. Bella isn’t the only winery combining wine with nature; nearby Amista Vineyard and Sutro Wine also offer similar wine and hike tours.

For a taste of Russian River Valley wines, stop by Bricoleur Vineyards. Instead of a standard tasting, you can opt for an elegant food and wine pairing or enjoy a laid-back picnic basket filled with delicious provisions (and, of course, wine), making it a perfect lunch spot.

If you’re ready for a break from wine, head to the open-air Fogbelt Brewing Co., which debuted in the summer of 2022. It’s a fantastic new addition to Healdsburg’s wine-centric drinking scene.

Activities Beyond Wine Tasting

Explore the Healdsburg Farmers’ Market and local farm stands

On Saturday and Tuesday mornings, be sure to take a leisurely stroll through the Healdsburg Farmers’ Market by Foss Creek Parkway. Grab a coffee and a pastry, then meander through a vibrant selection of local produce and goods, including artisanal mushroom jerky and sought-after fresh peaches that always attract a crowd.

If you miss the farmers’ market, several farm stands like Preston Farm and Winery (open daily) and SingleThread Farm at Dry Creek (open Thursday–Monday) offer excellent alternatives to sample local produce.

Discover new skills or participate in gleaning

Appellation is an exciting new initiative in Healdsburg, led by local chef Charlie Palmer. It consists of a series of food-and-wine-focused hotels, with the first set to open in Healdsburg in mid-2025, followed by locations in Petaluma, Sun Valley, and Pacific Grove. This brand aims to celebrate local bounty, featuring spacious guest rooms with large balconies, public areas with retractable walls for a seamless indoor-outdoor experience during spring and summer, and a chef’s table nestled in an orchard. Meanwhile, the Appellation team collaborates with local businesses to host a range of classes under the Crafted at Appellation program, covering topics from wreath-making at Setting Wines in Bacchus Landing to crafting cocktails and succulent terrariums.

Farm to Pantry is a community-focused organization committed to gleaning—saving food that would otherwise go to waste. Founded by Melita Love, who was inspired to act after seeing fruit rotting under her neighbor’s trees, the organization now mobilizes a team of volunteers (like you!) to collaborate with local farms, gardens, and anyone with surplus fruit to collect and distribute this produce to local food banks. In 2023 alone, they salvaged over 400,000 pounds of food.

Embark on a kayaking or cycling tour

For a bit of adventure before your next glass of pinot noir, consider joining a cycling tour with Russian River Adventures. While they've been running river trips for over two decades, they recently introduced a leisurely three-hour e-bike tour that meanders through vineyard- and forest-lined back roads. The electric bikes make it easy to pedal, and Bluetooth-enabled radios in each helmet allow participants to hear insights about landmarks from experienced guide Bruce Kramer.

Also based in Healdsburg, Getaway Adventures offers bike rentals (including e-bikes) along with a variety of cycling, kayaking, and combined tours. If you're torn between activities, their pedal-paddle tour provides a fantastic sampling of both experiences. Highlights include a picnic lunch nestled in a serene grove of redwoods between activities, with the chance to spot otters, egrets, and other native wildlife of the Russian River, if you’re lucky.

Spend a day swimming in a pool or relaxing by the river

A unique find in Sonoma wine country, Francis Ford Coppola Winery features a pool next to its tasting room that welcomes the public (for a fee; cabanas start at $220 for up to four guests). Open from June to October, guests can rent a bungalow or poolside chair (if available) and enjoy an afternoon sipping on rosé or piña coladas while soaking up the sun. If reservations are full, consider a day at Healdsburg Veterans Memorial Beach or Steelhead Beach for a more natural, BYOB experience swimming in the Russian River.

Getting there

For those traveling from the Bay Area, the best way to reach Healdsburg is by car, approximately a 90-minute drive north of San Francisco. Alternatively, the SMART train operates from the Larkspur ferry terminal to Sonoma County Airport, which is just a 15-minute taxi or rideshare trip from downtown Healdsburg—though there are plans to extend the line to Healdsburg in the future.

Sonoma County Airport (also known as Charles M. Schulz Airport) serves as the nearest airport for visitors arriving from outside the Bay Area, with direct flights available from Seattle, Portland, Los Angeles, Denver, Dallas, Palm Springs, and Las Vegas.