How to Plan a Healdsburg Honeymoon

Find out where to eat, drink, and stay in wine country.

Healdsburg valley

Photo by Rachel Ayotte

Countless Americans equate California wine country with Napa Valley. It’s a common association. Napa produces many absolutely fantastic vinos—not to mention award-winning cuisine. But Sonoma, the tall, not to mention gorgeous, county neighbor to the West, is severely underrated. Throughout the county, and especially in the delightfully small yet happening town of Healdsburg, are a multitude of vineyards and wineries with talented winemakers that look out of a dream. Plus, the region has countless organic and regenerative farms, vibrant restaurants, and original hotels. 

In other words, if you were to imagine a quintessential California wine destination, you’d conjure up Healdsburg—leafy green historic plaza and all. Compared to Napa’s known entities, the town still feels like a bit of an alluring secret. It’s a little bit off the radar and the vibe is very laid-back luxury. With much-anticipated new hotels, restaurants, and tasting rooms opening, it’s an exceptional destination for honeymooners (or anyone looking for a fun trip to wine country). Want to nail down your agenda? Here is a guide to our favorite spots around town. Most importantly, don’t forget to make reservations ahead of time!

Montage Healdsburg

Courtesy of Montage Healdsburg

Where to Stay

There's no shortage of stunning places to stay in Sonoma. If you want to stay in town, here are a few great spots to relax between wine tastings.

Montage Healdsburg

Vineyards, mountains and moss-draped oak groves—this brand-new luxury resort is a wonderland of idyllic Northern California landscapes with its very own hiking trail, not to mention active beehives. Good luck getting a dinner reservation at clamored-after hyperlocal restaurant Hazel Hill, not to mention a low-key glamorous room or sprawling suite. But when you do, it’s guaranteed to be worth the wait. (And don’t stress: the in-room dining menu is so divine you’ll be happy wherever you eat.) There’s tons to do on property (swimming in two pools, pickleball, archery, e-biking, and more), so don’t be surprised if you’re not inclined to leave. The exceptionally large—and beautifully scented—spa is even more of a dreamy deterrent, with oxygen facials and life-giving wraps, scrubs, and massages that include locally sourced honey and olive oil. 

Harmon Guest House

California art–filled and eco-friendly, this boutique hotel right off Healdsburg’s main plaza beautifully balances natural materials and high design. It’s spacious accommodations—king studios and suites—feel made for families, with plenty of little outdoor pockets scattered around the floors to socialize and gather in the fresh air. The firepit-studded rooftop is cozy and cool, too. In fact, it's the only one in the city that’s open publicly, and offers nibbles and sips that are a lovely way to end a day of wine tasting. There’s a small pool and yoga on the wooden deck; the staff is well versed in all the fun activities of Healdsburg, and can suggest and arrange outings like biking and standup paddle boarding on the Russian River. There’s even an option to volunteer as a “gleaner” and harvest produce at a local farm. 


This sister property to Harmon Guest House is a couple doors down under a living wavy green roof and boasts the acclaimed eatery Spoonbar—more on that deliciousness ahead. In keeping with the theme of Harmon, h2 is incredibly sustainable in its practices, bursting at the seams with artwork, and quite photogenic. This hotel, too, partners with local businesses and artists to periodically offer special amenities and showcases, lending each stay a bit more excitement as well as immersion into the supportive and tight-knit wine country community. 

Jordan Vineyard & Winery 

Craving an authentic French escape in California? The three just-reimagined suites—to the tune of $1 million—at Jordan Vineyard & Winery’s Chateau take cues from the old world, with rare antiques, soaring ceilings, custom beds, sumptuous textiles and linens, and elegant artwork. Large and bright, they feature seriously drool-worthy bathrooms, with statement-making soaking tubs and beautiful wall coverings, courtesy of interior designer Maria Haidamus. Beyond the one-of-a-kind suites, major appeal lies in sleeping at a working winery, where breakfast by the acclaimed culinary team is served in room with foraged tea, there is plenty of vino to be tasted, and there are 1,000-plus acres preserved as natural habitat to explore. 

Two Thirty-Five Luxury Suites 

For larger friend groups or families, this luxury escape comprising four three-bedroom suites right off the plaza is an ideal setup. With full kitchens, dining rooms, and living rooms, along with a trio of en-suite bedrooms, the downtown accommodations are super convenient and comfortable, making it an easy place to base yourself for walkable explorations.

The Matheson restaurant

Courtesy of The Matheson

Where to Eat

Culinary connoisseurs have no shortage of great places to grab a bite in Healdsburg. Check out some amazing places to book a table ahead.


You might be tempted to follow the intoxicating scent of Mary’s chicken cooked low and slow into this colorful, airy restaurant, which opens up to both the sidewalk in front and a large backyard studded with fire pits. Spoonbar’s seasonal dishes are as vivid as its design, thanks to the chef’s dedication to whatever is at peak freshness, which means rainbow California-centric plates that burst with flavor on your palate. Expect genuine servers offering enthusiastic and accurate descriptions of the menu to add to the temptation. Breakfast is served here for h2hotel and Harmon Guest House as well. 


This “modern country cuisine” restaurant offers garden dining at its best for lunch, brunch, and dinner five days a week. Green and lush, the setting definitely complements the cooking, which is informed by the motto: “Wherever you are, eat the view.” Local sourcing is at the heart of each item, whether it’s melt-in-your-mouth goat cheese croquettes using Sonoma cheese, bread, and heirloom tomatoes from a Healdsburg farm, or vino, of course. 

The Matheson

This new culinary destination on the Healdsburg plaza is so exciting you’ll probably want to visit twice—or thrice. That’s because it's acclaimed chef Dustin Valette’s passion project (make sure to also check out his eponymous restaurant down the street). Located in the building that was once his French immigrant great-grandfather’s bakery, The Matheson is made up of a trio of concepts. There’s the rooftop lounge, Roof 106, with a Mugnaini wood-fired oven, views of the plaza, fire pits, and a subtle bee theme where you’ll want to spend evenings; a sushi kitchen where chef Ken Tominaga works his magic; and a fine-dining spread by chef Valette that takes cues from Healdsburg’s micro seasons and many farmer collaborators. The wine bar is groundbreaking, too. There are a whopping 88 bottles offered by the glass—or taste. 

SingleThread Farm-Restaurant-Inn

The 11-course tasting menus—customized to guests’ dietary preferences—at this three Michelin-starred restaurant speak for themselves. The dishes are the culmination of husband-wife duo Kyle and Katina Connaughton, an acclaimed chef and regenerative farmer, respectively. Their farm is outside of town and provides much of what’s served in the warm restaurant, which is admittedly a tough reservation to get. You should also check out the pair’s latest venture, Little Saint, which is the town’s first plant-based restaurant. It features à la carte lunch and dinner menus, alongside design by Ken Fulk, artwork by Alice Warnecke Sutro and other female artists, quick-service options, and a wine shop. 

Oakville Grocery 

For bites on the go, there’s Oakville Grocery. This always happening corner spot—since 1881!—with a deli case of prepared salads and foods has made-to-order sandwiches and plenty of artisanal snacks, exceptional sips, and gourmand gifts. It’s a perfect place to get picnic supplies. 

Costeaux French Bakery

Another must with an impressive heritage is this French bakery, which opened in 1923. It’s hard to imagine a visit to Healdsburg would be complete without a morning pilgrimage to savor flaky-tender croissants, Pain Perdu (French toast made with delectable cinnamon walnut bread), quiche, and award-winning morning buns.  

Hazel Hill 

Blackberry lavender jam with made-in-house rhubarb coffee cake, fermented hot sauce created by the chef, zingy just-squeezed OJ, the best avocado toast of your life—these are just a few of the things awaiting you at breakfast at Hazel Hill, the signature restaurant of Montage Healdsburg. Hyper-fresh California cuisine meets French technique here, especially at lunch and dinner, which morph the given season into edible form. Plenty of cheeses, delightful veggies, and tasty proteins appear, as do specialties such as an outrageous côte de boeuf and various cuts of fish, duck, and pork. It’s all crazy good; you’re in safe hands. 

Journeyman Meat Co. Salumeria and Butcher Shop 

This beloved Healdsburg salumeria has a serious lineage—winemaker Pete Seghesio’s grandparents emigrated from Italy in the late 1800s and began perfecting the craft. Local farms’ seasonal harvest plays into each salumi, sausage, and cured meat they produce. Wood-fired pizzas and butcher cuts are on offer, along with gourmet products and wines. 

Flower Winery

Courtesy of Flowers

Where to Go Wine Tasting

With heavy influence from the Pacific coast’s sea breezes, Pinot Noir and Chardonnay are the dominating varietals in Sonoma. But, that’s far from all that’s being produced in Healdsburg. Reservations are always recommended. 

Flowers Vineyards & Winery 

Rosé all day starts at Flowers Vineyard & Winery, with a taste of the mouthwatering Rosé of Pinot Noir at the entrance of this new ‘House of Flowers’ hospitality center. But, that’s not even close to the whole story. Learn all about the winery’s super-special vineyards high on the California coast that bring such incomparably delicious notes to their signature estate Chardonnays and Pinot Noirs. Tastings are held outside in private cabana-like setups, with terraced gardens providing plenty of visual interest along with the gourmet bites that pair with side-by-side pours. It’s impossible to not fall in love. 

Bricoleur Vineyards 

This family friendly Russian River Valley winery is a former retirement center—for horses. The barn has been gorgeously rebuilt with reclaimed wood, and that’s just the starting point for unhurried visits full of fantastic wine—one range is cutely called Flying by the Seat of Our Pants—wandering to the pond and through grapes, feeding ducks and smelling roses and devouring incredible food. Top toques Charlie Palmer and Nate Appleman are culinary advisors and the food program is out of this world, including not only picnics and sit-down pairings but series of dinners, if you’re lucky enough to be in town for one. 

DaVero Farms & Winery 

The philosophy of this beautifully low-key winery and farm is “grow what belongs here. Be Patient.” And, it more than works for them. Rare Italian varietals the likes of which you’re probably not familiar (like Sagrantino) are in the happy-drinking lineup. These are all the result of biodynamic—read: the perfect amount of woo-woo—farming practices. There’s a sweet dog, giant pigs, and other animals to make visits feel very down to earth and unique.  

Lambert Bridge

For a stunning garden setting in which to sip Chardonnays, Zinfandel, Malbec, and Cabernet Sauvignon, there’s Lambert Bridge, a winery backdropped by redwood trees by Dry Creek. Nibble cheese and charcuterie while tasting bottles by their top female winemaker.  

Truett Hurst

With its flowing creek, farm animals, and consciously tended and biodynamic vineyards, Truett Hurst is a dreamy place to spend an afternoon. The single-vineyard vinos are expressions of the land, and it’s impossible not to taste the soul in these reds. 

Marine Layer Wines 

For an easily accessible tasting experience right on the plaza stop by the brand-new tasting room of Marine Layer, a bright and welcoming setting of moody blues, whites and earth tones with a cool playlist and fireplace to further set the mood. The cool-climate Chardonnays and Pinot Noirs this label is known for are on offer—both as flights and full glasses or bottles—alongside imaginative coastal bites by Sonoma’s Valley. There’s even a secret bottle shop where you can pick up wines from their friends’ labels plus imported Champagne. 

SUTRO wine hike

Courtesy of SUTRO

Activities to Try

Eating and drinking isn't the only thing to do in wine country. Take a break and get up to some other fun activities around town.


Want to get out in nature? Book a 45-minute guided nature hike with SUTRO Wine Co.’s founder and winemaker Alice Warnecke Sutro at the historic Warnecke Ranch & Vineyard, which sits on volcanic terroir in the Russian River corridor. Try the breathtaking guided four-mile estate hike with Jordan Winery or one through the vines at Alexander Valley Vineyards. Or, just explore by foot on your own, like at Riverfront Regional Park or Fitch Mountain Park and Open Space Preserve. 


The beautiful Russian River is not only the setting for world-class grape-growing and winemaking, but also lovely outings on the water. River’s Edge Kayak & Canoe Trips offers canoe and kayak tours, as well as SUP rentals for mellow adventures that can be interspersed with swimming, picnicking, and fishing.   

Ride Horses 

The Ranch at Lake Sonoma offers a variety of trail rides on horseback. For example, the Dry Creek Valley View Ride, which delivers eye-popping views for guests 12 years and up, can also be paired with a boxed lunch and wine tasting. 


Downtown Healdsburg with lively, leafy plaza is a perfect place to wile away a little time and peruse a number of homegrown boutiques selling everything from art and books to chic wine country–appropriate clothing and baby goods. (For the latter two, don’t miss Bon Ton Studio and new Bon Ton Baby).

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