The Perfect Healdsburg Weekend (with or without Kids)

Whether you're on a family trip or a couples weekend, there's plenty of fun to be had in the Sonoma wine country town of Healdsburg.
view of plaza in Healdsburg, California
(Photo: Kim Carroll)

With its boutique shops, upscale restaurants, and leafy downtown plaza lined with tasting rooms, it would be easy to mistake Healdsburg, California, for a typical adults-only kind of getaway. And while a Healdsburg weekend getaway is certainly a popular choice for grown-ups, this small Sonoma wine country town is also a surprisingly family-friendly hotspot. 

With or without kids, there’s no wrong way to spend a Healdsburg weekend. And when it comes to choosing where to stay, what to eat, and what activities to pursue, there’s even a surprising amount of overlap between what you can do with kids in tow and what you’d opt for as a vacationing adult. Even the most casual dining spots still offer killer wine lists, hotels deliver amenities that will delight travelers of all ages, and yes, you can find wineries that don’t just tolerate kids but actually welcome them. 

Healdsburg’s mix-and-match variety works whether your family travel moment means grabbing your significant other and hitting the road, piling the kids in the car and heading out, or meeting up with adult family for a fun Healdsburg weekend. Here are the top spots in Healdsburg to spark your getaway ideas. 

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Healdsburg Accommodations

The small town of Healdsburg goes big on lodging options. With more than 30 places to stay within city limits at price-points that range from wallet-friendly to ultra-luxe, a Healdsburg weekend is an accessible adventure for all budgets.

Where to Stay on a Healdsburg Weekend with Kids

View of room at Hotel Trio in Healdsburg, California
Hotel Trio (Photo: Kim Carroll)

Comfortable digs; plenty of room for downtime, naptime, and bedtime; a kitchen; and communal spaces like fire pits, grills, and a pool make Hotel Trio a perfect family-friendly hotel in Healdsburg. This long-stay Marriott-portfolio hotel sees weekday business travelers, but on weekends, it’s a magnet for families and groups looking for that little bit of extra space and amenities like free breakfast, a robot named Rose that will deliver items to your door, and the ability to connect to your own streaming services via the 55-inch in-room flatscreen TV. 

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Located a five-minute drive from downtown Healdsburg, Hotel Trio has plenty of free parking and is right across the street from a large local market featuring plenty of local fare (including English muffins from Costeaux). 

Review Highlights: Guests praise this TripAdvisor favorite hotel for its large and modern rooms, new and clean common spaces, and helpful and friendly staff.

Where to Stay on a Healdsburg Weekend with or without Kids

Pool and garden at Hotel Healdsburg in Healdsburg, California
Hotel Healdsburg (Photo: Hotel Healdsburg)

The Hotel Healdsburg offers everything you need for a proper grown-up Healdsburg weekend getaway, including rooms outfitted with luxe linens, custom furniture and art, and in some cases, soaking tubs. In-room snacks and hearty breakfasts come with the nightly rate, and there’s plenty of room to relax at the pool ringed by a garden of olive and fig trees.

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The hotel’s prime location on Healdsburg’s town plaza puts the charming downtown’s restaurants, tasting rooms, and shops within strolling distance. Bring the kids and they’ll love the pool and the proximity to pizza and organic soft-serve at Pizzando, the upscale pizza joint attached to the hotel. 

Review Highlights: This TripAdvisor Travelers’ Choice 2021 recipient earns high marks for its excellent location and hip decor.

Healdsburg’s Best Dining Options

Bar at Campo Fina in Healdsburg, California
Campo Fina (Photo: Christine Sarkis)

Healdsburg is nothing short of a dining wonderland. From casual spots that welcome kids to Michelin-starred restaurants geared to serious diners only, the town excels at fresh, creative food that pays tribute to the surrounding bounty of Sonoma.

Where to Eat in Healdsburg with Kids

Where picnics rule, bakeries take center stage. Stop by one of Healdsburg’s standout bakeries for breakfast and while you’re there stock up on provisions for an outdoor lunch. Famous favorite Costeaux French Bakery occupies a lofty space filled with the aromas of baking bread. Sit down for weekend brunch favorites like eggs benedict or quiche, then grab sandwiches, artisanal breads, and over-the-top gorgeous European cakes to go. Or check out farmers-market-fave turned brick-and-mortar Quail and Condor for ultra-rich kouign ammans, chocolate chip cookies that rock the line between crisp and chewy, and breads fit for picnic royalty. 

Where to Eat in Healdsburg with or without Kids

Part of the fun of Campo Fina is finding it. Pivoting early in the pandemic, the restaurant closed its usual indoor entry on Healdsburg Avenue and now routes customers up an unassuming alley off Center Street near the plaza. Find your way back to the bustling covered patio, though, and you’ll be rewarded with a menu that merges seasonal Sonoma inspiration with ancestral Italian recipes. A large wood oven turns out perfectly crisp pizzas and the tables are spaced out but still offer the feeling of a bustling hotspot.

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The vibe is casual and warm enough for kids to blend into the scenery, but adults will appreciate the chance to linger over a wine list that spotlights local wines and beer. 

Healdsburg Wineries

View of picnic area at Bricoleur Vineyards in Windsor near Healdsburg, California
Bricoleur Vineyards (Photo: Bricoleur Vineyards)

Wineries with kids? It’s not just possible—pick the right one and it can be fun for everyone. And yes, even in laid-back Sonoma there are wineries that don’t welcome the littles, but there are just as many that do. 

Healdsburg Wineries to Visit with Kids

Amista, Healdsburg’s Dry Creek AVA’s local sparkling house, has a relaxed, warm, and friendly vibe that leaves plenty of room for little ones. The shaded patio off the tasting room flows effortlessly into the vineyard. Kids can roam the rows—and at harvest time, even measure and taste the grapes—while adults sip estate-grown sparkling wines, including hard-to-find sparkling grenache and syrah.

The winery has a self-guided vineyard tour with signs that explain the grape-growing and wine-making process. The stroll around the vineyard is a great way for kids and dogs (the winery is also dog-friendly) to work off some extra energy while soaking up some signature Sonoma sun. The tasting room offers a number of food-and-wine pairings, and its signature savory lemon popcorn is always on offer. 

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Healdsburg Wineries to Visit with or without Kids

Bricoleur Vineyards is a relatively new addition to the local landscape, but sets itself apart by excelling at the fine art of gathering, which—whether you’re a family, a couple, or a group—means everything right now. Tucked down a country road in the neighboring town of Windsor, Bricoleur unfolds across expansive patios, an airy and inviting central tasting barn, and dozens of tucked-away picnic spots, all perfect for whiling away a few hours.

Rose and kitchen gardens, ponds, bocce ball courts, and even a chicken coop reward exploration. Everything here moves at a relaxed pace, from the food-and-wine pairings from chef Evan Castro (formerly of downtown Healdsburg’s Chalkboard) to the packed picnic, an abundant selection of creative dishes that offer just the sort of casual al fresco feast that’s equally perfect for couples who want a quieter setting and families who don’t want to corral little ones at a table. 

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Christine Sarkis
Christine Sarkis is a traveling parent and longtime travel writer and editor. The former executive editor for TripAdvisor travel magazine SmarterTravel.com, Sarkis has spent nearly two decades finding and sharing the best places to go with an audience of enthusiastic travelers. Her stories have appeared on USA Today, Conde Nast Traveler, Huffington Post, and Business Insider. Her expert advice has been quoted in dozens of print and online publications including The New York Times, Conde Nast Traveler, and People magazine. She has also shared travel tips on television and radio shows including Good Morning America, Marketplace, and Here & Now. Her stories have been published in the anthologies Spain from a Backpack and The Best Women's Travel Writing 2008, and she is working on a travel memoir.

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