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How to Plan a Romantic Getaway in Healdsburg

If you’re planning a couple’s getaway to the Sonoma wine country, the enchanting town of Healdsburg can really turn up the heat.

Jess Lander, Contributing Writer

There’s romance to be found all throughout wine country — what’s more romantic than wine and panoramic vineyard views? — but if you’re planning a Sonoma couple’s getaway, the adorable and enchanting town of Healdsburg can really turn up the heat. Located roughly 90 minutes from San Francisco, here are the most romantic getaway ideas in Healdsburg to stay, sip wine, relax, and play with your amore. 

BEST TIMES TO VISIT

Sonoma is blessed with an (almost) always sunny, moderate climate year-round, which means there truly isn’t a bad time of year to visit. The bulk of harvest takes place in September and October, and while this is traditionally the busiest season, high temperatures and wildfires in recent years have made these month’s slightly less desirable to visitors. You might instead consider February and March, during which you’ll likely catch the mustard bloom. A stunning, bright yellow carpet of mustard flowers cloaks the valley floor for about a month and makes for some seriously stunning photos. It’s also the off-season, so you’ll find smaller crowds, less traffic, and lower prices on lodging.

Where to Stay

For a Romantic Getaway in Healdsburg


Montage Healdsburg

Healdsburg’s newest resort is the epitome of wine country luxury. Book one of the Montage’s tree house-esque bungalows, equipped with incredible views, an outdoor terrace and firepit, and in some cases, an outdoor shower. Without leaving the resort you can dine at the on-site, Michelin Star-worthy restaurant, relax at the adult-only pool, and book a couple’s massage.

Healdsburg Sonoma - Montage Healdsburg by Jess Lander
Montage Healdsburg, Photo by Jess Lander

Harmon Guest House

Located right on the Healdsburg Plaza and within strolling distance of the town’s top shops, wine tasting rooms, and restaurants, this architecturally-stunning and sustainability-focused hotel has just 39 rooms, so it maintains a level of intimacy, despite being right at the center of Healdsburg’s hustle and bustle. Don’t miss happy hour on the rooftop bar, which offers some of the best views around. 

Where to Sip

5 Romantic Healdsburg Wineries to Visit


Flowers Vineyards & Winery

Cozy up in a chic garden cabana at Flowers Vineyards & Winery. The Bottles & Provisions Experience is one where you’ll pretty much be left alone to sip wine and nibble through a gourmet picnic basket at your own pace for uninterrupted quality time. 

Healdsburg Sonoma - Flowers Vineyards & Winery by Jess Lander
Flowers Vineyards & Winery. Photo by Jess Lander

J Vineyards & Winery

There’s no better way to toast an anniversary or long-lasting love than with bubbly and J Vineyards has the goods. To make your visit extra special, book a reservation in the stunning Bubble Room, which acts as a fine dining restaurant. You’ll be treated to a five-course meal prepared by Michelin-trained chef Carl Shelton, and each dish is paired with a still or sparkling wine.

MacRostie Winery

The glass-walled MacRostie Estate House offers some of the best vineyard vistas in Healdsburg wine country. Snag a table on their terrace and soak it all in while sipping single-vineyard Pinot Noir and Chardonnays from the Russian River and Sonoma Coast. You can also add on a food accompaniment, like a cheese and charcuterie box or a veggies platter. 

Jordan Winery

Jordan Winery can transport you to the most romantic city in the world with its Paris on the Terrace experience. Sit at bistro tables shaded by beautiful oak trees with Jordan’s iconic chateau as your backdrop. French music will drift through the air as you enjoy classic Parisian bistro fare made with ingredients sourced right from Jordan’s gardens and estate. The lunch is paired with real Champagne, plus Jordan’s Cabernet Sauvignon and Chardonnay.  

Healdsburg Sonoma - Jordan Vineyards & Winery by Jess Lander
Jordan Vineyards & Winery, Photo by Jess Lander

Ferrari-Carano Winery

If it’s being offered, start one morning of your Healdsburg getaway with an Italian-style brunch at Ferrari-Carano Vineyards paired with a flight of wines. Before you leave, take some time to stroll through their incredible five acres of gardens, which in the springtime, bloom with over 10,000 tulips and daffodils. It’s one of the most beautiful proposal spots in Sonoma. 

Things to Do

Besides Sipping Wine


Explore the Russian River

Rent a kayak, canoe, or stand-up paddleboard and cruise the Russian River, or in the summer, float down it in an inflatable, a favorite activity of locals. There are also plenty of little rocky beaches along the river for picnicking. 

Save Time for a Spa Day

If you’re on a romantic getaway, why not schedule a spa day? Several of Healdsburg’s luxury hotels and resorts have stunning spas that offer couples treatments. Check out Hotel Healdsburg and the Montage.

Healdsburg Sonoma - Hotel Healsburg
Hotel Healdsburg, Photo by Jess Lander

Bike Through Wine Country

One of the best ways to experience the picturesque, country backroads of Healdsburg’s wine country is via bike. Through Getaway Adventures, you can even book a Healdsburg bike and wine tour, which stops at a few wineries in the Dry Creek Valley along the way. Or, if you want a self-guided experience, you may want to rent an electric bike, which will give you some assistance up and over the rolling hills. 

Splurge on a Once-in-a-Lifetime Dining Experience

Foodies will want to snag a reservation at SingleThread, a three Michelin Star restaurant located on Healdsburg Plaza. Though pricey, this three-to-four hour dining adventure that’s hyper focused on fresh, seasonal, and local ingredients — plus, has a bit of a Japanese infusion — is guaranteed to be one of the best meals of your life. Book well in advance of your trip, for they fill up quick. 

Healdsburg Sonoma - SingleThread

Shop the Plaza

The quaint and charming Healdsburg Plaza is lined with independently-owned clothing boutiques and even a few funky specialty stores, like Mr. Moon’s novelty and gift shop and Hopscotch Gifts & Gallery. The Plaza is definitely worth a stroll one afternoon and you can stumble upon some great spots for Happy Hour drinks, too, like Spoonbar or Duke’s. Noble Folk Ice Cream is a must on a hot summer day. 

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Jess Lander wine writer

Jess Lander

Jess Lander is a freelance wine, booze, food, and travel writer based in Napa Valley. She’s a regular contributor to Wine Enthusiast, VinePair, Wine Business Monthly, 7×7, Eater SF, Sonoma Magazine, Napa Sonoma Magazine, and the Napa Valley Register. Her work has appeared in many other publications, including Decanter, AFAR, Lonely Planet, and the SF Chronicle. She is also the author of The Essential Napa Valley Cookbook.