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Welcome to Healdsburg, California, one of the most charming towns in Sonoma County. It’s always a pleasure to return to this exciting culinary and wine mecca with its special connection to Northern California.

Healdsburg has a quiet reputation for a laid-back experience. But its recent boom of renovations, reopenings, and new businesses has revamped just what a visit means today. Everything that is new and exciting in wine country has been opening in or nearby to Healdsburg. I knew I was desperately overdue for a visit — so much so, I visited twice in a few weeks’ time.

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The most invoking part of all of this excitement is the places to visit for the design-minded traveler. A chic luxury resort, an art-forward boutique hotel, a completely plant-based restaurant, and wineries as pretty as a postcard. You couldn’t ask for more on a weekend jaunt up the Sonoma Valley.

And you can’t overlook the tried and true restaurants and wineries of Healdsburg, the very longstanding foundation for this intimate and growing community. Many of which have ties to these new digs. It’s a beautiful blend of both, providing a one-of-a-kind Northern California getaway.

So it’s with great pleasure to share where to say in Healdsburg, where to eat, and the best things to do while visiting. You may find yourself taking a few trips just like I did myself.

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The Ultimate Travel Guide to Healdsburg, California


Getting to Healdsburg, California

North of San Francisco, getting to Healdsburg is quite easy. It’s the perfect destination for a road trip. The closest international airport is San Francisco (SFO) where I recommend renting a car as it will be most helpful for getting to the wineries and other activities in Sonoma. Head north over the scenic Golden Gate Bridge, and you’ll be there in no time.

Alternatively, one hack to visit sans the car is to fly into SFO and take the Airport Express bus from SFO to Sonoma County Airport. From there, hop into an Uber or Lyft into town (booking somewhere on the plaza is ideal). You can use Uber/Lyft to get around Healdsburg if you plan to visit wineries outside of town.

Amount of Days in Healdsburg

As a personal recommendation, I would recommend no less than two nights in Healdsburg. It will give you ample time to visit a few wineries, and the plaza, and dine at a couple of restaurants.

While Healdsburg makes for a wonderful day trip for Bay Area locals, I’d stay longer if flying in or those wanting a weekend getaway. Pro tip: book in for the long weekend to take advantage of pool time.


Frequently Asked Questions About Healdsburg

Is it better to stay in Sonoma or Healdsburg?

For those wanting a robust option of things to do in close proximity, staying in or within earshot of Healdsburg is recommended. Sonoma County encompasses a larger area spanning over a few hours of time in the car. Healdsburg has it all in one place.

Is Healdsburg in Napa or Sonoma?

It is located in Sonoma County and is a premier Northern California wine region. You’re not far from Napa, so you could consider visiting both areas over the span of a few days.

Is Healdsburg worth a visit?

Absolutely! Whether it’s for a day or a weekend, Healdsburg has so much to love. From farm-to-table dining to award-winning wineries, there’s a lot to enjoy in this small city.

How do I spend a day in Healdsburg?

A day trip to Healdsburg is a great option (especially for those nearby!), and you can easily make the most of your time there. With one day, I’d recommend picking a restaurant for lunch and dinner from below, and 2-3 activities.


The Best Hotels and Resorts In Healdsburg, California

While there are several stunning hotels in downtown Healdsburg and nearby, these are my handpicked selection for a weekend in Healdsburg after visiting both hotels to experience their offerings. Both hotels offer different opportunities to experience Healdsburg, each memorable in its own way.

Travel Guide to Healdsburg, California

Montage Healdsburg

The premier luxury resort group Montage opened up its well-awaited doors in Healdsburg in the winter of 2021. Since then, it has risen to one of the best luxury resorts in Northern California, and for good reason. The 130 bungalow-style rooms and suites are spread out across vineyards and oak trees with incredible views.

Each suite and room have a contemporary yet intimate design, opening up to nature and feeling like it’s one with its surroundings. Inside, luxury amenities like soaking tubs, outdoor showers, and expansive patios with a firepit. The suites at Montage Healdsburg are also some of the grandest — most at 940+ square feet.

But beyond the suites and rooms is a robust hotel program that sets apart Montage from the rest. One of the most family-friendly resorts around, there’s an activity center with complimentary electric bikes (and more activities), a children’s play center, and even a resident canine ambassador who comes around to say hi. If you’re wondering where to take your family in wine country, this is it.

The Montage Healdsburg has two pools to enjoy, one specifically for families and an adult option as well. Both offer beautiful views of St. Helena Mountain and a chance to rest while visiting. You’ll find a spa and full gym to enjoy at your leisure as well.

While visiting, don’t miss a chance to dine at Hazel Hill, the main restaurant at Montage Healdsburg. While the breakfast is incredible, like their delicious waffles, the dinner service is not to be missed. Start the evening out with drinks on the patio and stroll into the restaurant for a taste of Sonoma-inspired French cuisine.

Good for: families, couples, friends’ getaways, and solo travel. Find the best rates here.

The Madrona

A boutique hotel set out in the countryside of Healdsburg, The Madrona is a design lover’s dream. Led by designer Jay Jeffers, the beautifully appointed manor received a stunning renovation before opening in spring 2022.

The tree-lined driveway takes you to the historical manor, where guest suites and rooms are found in the half-dozen buildings. Each room is unique in design, featuring elevated amenities like Flamingo Estate bath products, fireplaces, and an in-room minibar. Daily breakfast is included with the nightly rate, set inside the light-filled bar downstairs.

While on the property, dip into the saltwater pool and sunbathe next to the iconic orange orchard. And don’t miss a meal at the Restaurant, one of the best bites in town right now. If you’re there on a Wednesday, you’re in luck for their very much talked-about fried chicken experience.

Good for: couples, friends’ getaways, and solo travel. Find the best rates here.

Read More: The Best Hotels in Healdsburg

Vista Luna Sonoma Luxury Container Home (Airbnb)

One of the most amazing Airbnbs I’ve stayed at and only 15 minutes from downtown Healdsburg is Vista Luna Sonoma. Set in the hills with 360-degree views over the valley, this modern meets charming home is a wonderful choice for a vacation rental. I had the pleasure of spending three nights in this 3 br/2 ba home.

The home is set with every amenity you could possibly need. The inside is equipped with a luxury kitchen, a Nespresso machine, and more. Outdoors, find a pool, jacuzzi, gas firepit, lawn games, and even a movie projector. It’s a wonderful place to call home to explore the Sonoma area and beyond.


Where To Eat In Healdsburg, California

Where to dine in Healdsburg? The list as you can tell is *endless.* I’ve narrowed it down to the best newcomers to open these last few years, and the tried and true you can’t miss.

The Restaurant & Bar at The Madrona

Set inside the Madrona Hotel in the countryside, the “Restaurant” at the Madrona is reason enough to visit. Lunch or dinner, you can’t go wrong with either. Fresh takes on local fish, and fried chicken, and do not miss that trout dip topped with a healthy serving of roe.

Hazel Hill at The Montage

Elevated, seasonal cuisine finds itself presented absolutely beautifully at Hazel Hill. Set inside The Montage Healdsburg, the restaurant is perched up in the oak trees with incredible vineyard views. It’s an airy, light-filled setting. While you can dine in for any meal, I’d recommend snagging a reservation for dinner around sunset time.

The Matheson

The latest from local Chef Dustin Valette opened this last fall, and there’s a bit of everything at this one spot. Set across three levels, you’ll find a rooftop bar, a prix fixe menu in the main restaurant, and two bars.

Molti Amici

One of the newest restaurants to open in Healdsburg, Molti Amici is a hotspot for Italian food. Wood-fired pizzas, housemade pasta, and an amazing cocktail + wine list are highlights here.

Troubadour

Need a meal on the go? Don’t go further than Troubador for one of the best deli sandwiches in the area. It’s elevated and from the minds of past SingleThread chefs who also do Quail & Condor.

SingleThread

There is nothing more tried and true than SingleThread for fine dining in Sonoma County. While it’s a tough reservation to get, those who do take part in several course experiences, centered around Japanese technique and Sonoma ingredients. It’s a meal to talk about for ages, with 3 Michelin stars.

Little Saint

Locals will remember what was originally the Shed, is now Little Saint. 100% plant-based, featuring a bar, coffee shop, restaurant, and a small provisional market. The folks at SingleThread had some hand in opening this joint, so you know it’s all very well dialed in. Do order the “grilled cheese” and grab a coffee to-go from their bar (they’re serving SF-based Saint Frank coffee.)

Willi’s Seafood & Raw Bar

A great classic to Healdsburg Plaza, pop into Willi’s for all of your seafood needs. Think East Coast meets South America for the flavor profile, and do reserve a table in advance.

Quail & Condor

I like to save this spot for right when we leave town as it’s conveniently not far from the freeway onramp. Previously at SingleThread, the owners here make a serious selection of fresh artisanal pastries, bread, and other delicious bites. Nothing like a road pastry to tie you over.

Flying Goat Coffee

Slightly partial, but I think this is the best coffee on the square.

A few other notable favorites:

  • Noble Folk Ice Cream & Pie Bar for unique flavors
  • Barndiva is a total Healdsburg classic place for a bite-to-eat
  • Oakville Grocery is the spot to grab all of your picnic needs
  • Valette for the high-end restaurant by Chef Dustin Valette
  • Chalkboard for great, seasonal-menu restaurant

What To Do In Healdsburg, California

Join SingleThread For an Experience at Their Farm

If you’re not able to snag a reservation at their restaurant, SingleThread Farms has opened up its location in Dry Creek Valley for visitors. There are a few ways to experience their farm, the first is to pop into their highly curated Farm Shop. Inside, Japanese goods, farm florals, and other housemade kitchen goods are available for purchase.

The second opportunity to experience the incredible SingleThread Farm is to join one of their weekend experiences. From floral classes to agricultural tours, they’ve opened up their farm to guests to experience everything that goes into their practice. It’s a small group tour, and each month there is something new to enjoy. Book experiences here.


Embark On An Epicurean Meets Wine Tour at Jordan Winery

Healdsburg has several wineries to choose from for wine tasting, but a few have some standout experiences. Jordan Winery is a longstanding favorite for an estate experience that combines both food and wine. It starts with a continental breakfast on the patio, followed by a tour in a Mercedes Sprinter through the estate.

From there, you’ll have alfresco wine tastings in plein air as you learn about their winemaking process. It’s followed by a lunch and wine pairing hosted at the Vista Point. The estate Chef prepares dishes that match perfectly with their Russian River and Alexander Valley-grown wines. Book the tour here.


Travel Guide to Healdsburg, California

Stroll and Shop the Healdsburg Plaza

I’d block out a good few hours to stroll and shop through Healdsburg Plaza. The square has welcomed many new faces over the last few years. Start your time in a stunning tasting room at Marine Layer Wines for their free-spirited wines.

Head over to Ciao Bruto which sells all of the wine and provisions you could need from Italy (an absolute feast for the eyes). Stop by Bon Ton Studio, a lovely curated store of home goods, and fashion finds for both mom and baby. I’d pair the whole afternoon with a meal like lunch at Little Saint, or an early dinner at The Matheson.


Get A Taste of Sonoma Coast at Flowers Winery

Synonymous with the California coast, Flowers Winery is set inside one of the most incredibly designed wineries around (so chic!). But much more than a stunning place to sip on wine, Flowers Winery has been producing iconic Chardonnay and Pinot Noir varietals for 30 years.

I’d suggest booking in for the “Estate Vineyard Immersion” where you’ll journey through their estate wines that share the story of their winemaking process. The entire experience is led by a wine expert who gives an in-depth look at the wines while you sit back in either their Provencial gardens or inside the swoon-worthy space. The tasting is accompanied by seasonal bites prepared by the culinary team designed to elevate the wines. Book your experience here.


Travel Guide to Healdsburg, California

Take a Hike in Armstrong Redwoods State Natural Reserve

Not everything is wine-focused in Sonoma County. Stretch your legs out in Armstrong Redwoods’ 805-acre park that features soaring California coastal redwoods. There are several trails to explore, so while you can easily wing it, I’d give you some time to decide where you want to hike prior to arriving.

For first-time visitors, the best trail is the Armstrong Nature Trail which is self-guided and gives you lots of information on the redwoods through posted displays. Another favorite trail is the Discovery Trail, a smaller trail that winds through the trees.


Travel Guide to Healdsburg, California

Soak In The Views and Taste Wine at Gary Farrell Winery

Handcrafted wines meet unparalleled Sonoma views. Book in at Gary Farrell Winery for both reasons. When you do reserve, aim for a sunny day and request to sit on the terrace as you work through their library of Russian River Valley wine.

By appointment only, the “Elevation Tasting” pairs their vineyard designate wines with artisan cheeses. It’s the perfect mid-morning or late-afternoon tasting, in my opinion. As you taste their wines, you’ll enjoy incredible views of the redwoods. Book the tasting here.


Book a Bohemian Highway Tour

While you can arrange a driver to bring you through the best of Sonoma’s outdoor destinations and wineries, there’s nothing quite like a Bohemian Highway Tour. They offer handcrafted, small group experiences ranging from “Wine & Design” to “The Explorer.”

The Wine & Design tour for instance takes place in a luxury SUV like their Land Rover Defender 110 (based on availability), and their concierge team puts together a bespoke itinerary. It includes 2-3 stops at design-focused wineries, followed by a chef-prepared seasonal lunch. Book the tour here.


Forage for Wild Mushrooms on The Sonoma Coast

Home to an abundance of wild mushrooms, the Sonoma Coast is the premier Northern California destination to forage. I think this is one of the most unique experiences to be had in the Sonoma area, so much so, it almost always has a waitlist.

Forage SF runs boutique 3-4 hour group foraging tours on the coast to hunt down local mushrooms. It’s set out near Jenner (~50-minute drive from Healdsburg), and Chef Patrick Hamilton leads the way. Book the tour here.


Unwind at Spa Montage

There’s no better way to retreat while in wine country than with some spa time. The premier spa in Healdsburg is certainly Spa Montage. Whether or not you’re staying on the property, you can book one of their treatments inspired by nature.

I’d suggest their Signature Facial, designed to clean and revitalize your skin no matter what season. Your aesthetician goes through a series of cleansing and nourishing treatments, along with an arm and hand massage. Afterward, unwind in their steam rooms and relaxation area. Book a treatment here.


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Xx,
Jessica

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