Best Wineries
Healdsburg: Everything You Need to Know

Healdsburg: Everything You Need to Know

By Published On: July 11th, 2022

Where to stay, wine taste, dine and more!

Nestled along the Russian River in the heart of Sonoma Wine Country, Healdsburg offers a mix of Northern California ease and European charm, stunning vistas, and award-winning vintages.

All of this centered around a charming town plaza lined with shops, restaurants, tasting rooms and galleries.

At the epicenter of three premier wine regions – Russian River Valley, Dry Creek and Alexander Valley, Healdsburg is home to more than 160 wineries and endless outdoor activities including “wiking” (wine + hiking), cycling, kayaking down the Russian River, horseback riding and more. 

Where to stay

Whether visiting for a romantic escape, family vacation, girlfriend’s getaway or outdoor adventure, travelers are bound to find the perfect place to stay among the town’s diverse hotels, inns and suites.

Luxury In Healdsburg

Nestled among 258 acres of rolling vineyards, Montage Healdsburg is a luxurious Wine Country escape, home to the 11,500-square-foot Spa Montage. Treatments use botanical blends crafted from plants around the property, a zero-edge resort pool, three signature dining options inspired by the region’s culinary heritage including Hazel Hill, and endless activities from yoga among the vineyards to stargazing with the resort’s Constellation Concierge.


From an undulating living roof alive with succulents and greenery, to a rustic boho vibe with striped bamboo flooring in the guestrooms and reclaimed wood chandeliers, the LEED Gold certified h2hotel is an eco-friendly gem.

The hotel features eco guestrooms, a Contemporary American restaurant, Spoonbar, a solar heated Creekside pool, complimentary bike rentals, and artwork and installations found throughout the property.

Healdsburg History

Set in peaceful, English country-style gardens, the charming Queen Anne-style Grape Leaf Inn offers 13 romantic rooms decorated with antique furnishings, skylights, ceiling murals, fireplaces, stained-glass windows and 4-poster beds.

Groups can also reserve the inn’s 1920’s bar tucked away behind a secret bookcase known as The Speakeasy. 


Hotel Trio is a stylish hub in for exploring Sonoma Wine Country with family and a warm setting to unwind and reconnect.

Families will enjoy the property’s bicycle rentals for exploring the area, outdoor BBQs and fire pits with s’mores kits, full kitchens in each suite for home-cooked meals while traveling, and a spacious pool and bocce ball court for family fun.

Guests can also take advantage of Rosé the Robot, a robot butler that offers a touchless experience when delivering items to guestrooms including extra pillows, ice cream and snacks.


Nestled in the Dry Creek Valley, Healdsburg is perfectly positioned in the center of three renowned wine growing regions. With the Alexander Valley to the northeast and Russian River Valley to the south, area wineries are producing exquisite varietals from hearty Zinfandels to delicate Pinot Noirs.

Jordan Vineyard & Winery

Travelers can experience French-inspired wines and beautiful views of the Alexander Valley at Jordan Vineyard & Winery.

The winery offers various tours and tastings including a walking tour to explore the spacious estate followed by a seated wine tasting with food pairings in the property’s cellar room, a French-inspired hideaway filled with hundreds of wine bottles and priceless winemaking antiques. 

Healdsburg: Everything You Need to Know
Jordan Vineyard & Winery.

Flowers Vineyards & Winery

Combining the beauty of natural foliage with world-class winemaking, Flowers Vineyards & Winery offers unique expressions of the Sonoma Coast through Pinot Noir and Chardonnay. Visitors can enjoy the Flowers Flight which features a guided tasting of coastal wines accompanied by seasonal bites crafted by the House of Flowers culinary team.  

Healdsburg: Everything You Need to Know
Flowers Vineyards & Winery

Truett Hurst Winery

Positioned perfectly on the edge of the Dry Creek, Truett-Hurst Winery offers Creekside Adirondack chairs and picnic tables where guests can enjoy a glass of Salmon Run Zinfandel and, if they’re lucky, spot one of the namesake fish as they spawn in the creek.

Healdsburg: Everything You Need to Know
Truett-Hurst Winery Outdoor Tasting.

Tasting Rooms

The Healdsburg Plaza, which dates back to the 1800s, is the centerpiece to the town and is home to more than a dozen tasting rooms. Travelers can spend the entire day bopping around downtown tasting rooms without ever having to drive outside of town for a wine tasting. 


Just a few steps from the corner of Healdsburg Ave. and Matheson St., Siduri specializes in Pinot Noir grapes grown in cooler climates, including California’s Russian River Valley, Salinas Valley and Santa Rita Hills as well as the Willamette Valley in Oregon.

The tasting room takes guests on a nautical international journey all while tasting wines in the heart of Healdsburg. 

Healdsburg: Everything You Need to Know
Siduri Tasting.

Breathless Wines at Healdsburg

Located just a short walk from Healdsburg Plaza, the Breathless Wines tasting room and garden is a must-visit for sparkling wine lovers. The tasting room features an outdoor patio and gazebo surrounded by redwoods and cypress trees, making it a perfect place to enjoy a chilled glass of sparkling wine on a warm day. 

Healdsburg: Everything You Need to Know
Breathless Wines Spread.

Young & Yonder

Although in Wine Country, wine isn’t the only Healdsburg libation visitors can enjoy. After a day of wine tasting, guests can switch up their beverage with a visit to Young & Yonder for a seasonal cocktail tasting. 

Healdsburg: Everything You Need to Know
Young & Yonder.

Healdsburg Restaurants

Home to six Michelin Star restaurants, Healdsburg is a culinary epicenter in the heart of Wine Country. The tastemakers and trendsetters who make Healdsburg their home truly embrace the farm-to-table culture and strive to incorporate what is uniquely Sonoma into every bite. 

The Matheson

A new restaurant from Chef and vintner Dustin Valette and partner Craig Ramsey, The Matheson is a tri-level, modern restaurant and rooftop bar offering farm-focused dishes, sushi kitchen and a Wine Wall with 88 wines on tap.

Healdsburg: Everything You Need to Know
The Matheson Wine Wall.

Little Saint

SingleThread owners Kyle and Katina Connaughton recently introduced a plant-based full-service restaurant, quick-service cafe and wine shop known as Little Saint.

With an à la carte menu inspired by the seasonal bounty of the Sonoma Valley, the restaurant features an uplifting gathering place where food, music, art and conversations collide.

Healdsburg: Everything You Need to Know
Little Saint.

Costeaux French Bakery

A piece of Paris in California Wine Country, Costeaux French Bakery has been family-owned and serving guests artisan breads, French café classics, signature desserts and divine coffee since 1923.

Healdsburg: Everything You Need to Know
Cinnamon Walnut Bread at Costeaux French Bakery.

Costeaux French Bakery remains a treasured local gem in downtown Healdsburg for breakfast, brunch and lunch, and offers gourmet boxed lunches to bring on picnics.

Healdsburg: Everything You Need to Know
Costeaux French Bakery.

Healdsburg Shops & Activities

When travelers had their fill of eating and drinking, the historic square is a great place to find one-of-a-kind artisan items from clothing and jewelry to gorgeous art pieces. Or, the destination’s flowing rivers, towering redwoods, rolling vineyards and the peaks of the Mayacamas Mountains create the perfect backdrop for outdoor adventure. 

The Harris Gallery

Founded by M.C. Harris and his son, A3L3XZAND3R, The Harris Gallery combines the duo’s love for wine and art in its downtown gallery. Visitors can book an ART + WINE tasting in The Harris Gallery’s newly renovated indoor tasting lounge or enjoy the open-air in the gallery’s shaded outdoor cabines.

Healdsburg: Everything You Need to Know
The Harris Gallery

Bon Ton Studio

A perfect stop for a girl’s day, Bon Ton Studio carries beautiful clothing and an evolving collection of soft goods and home décor from artisans all over the world.

Wiking (wine + hiking)

Combine wine tasting with outdoor exercise on a signature “wiking” (wine + hiking) tour at Sutro Wine Co. (which features a guided tour with the female founder and owner, Alice Warnecke Sutro) or Notre Vue Estate Winery & Vineyards.


Visitors can explore the backroads of Healdsburg with Getaway Adventures, which leads a Healdsburg Sip ‘N Cycle tour, take a relaxing e-bike tour out to Wohler Bridge with Russian River Adventures, or alongside a pro with the exclusive Pro Cycling Experience with Pete Stetina.

Healdsburg: Everything You Need to Know
Getaway Adventures.

For something a bit different, Bike Healdsburg offers tours of downtown on a group party bike, which is powered by the pedaling of 10 people. Tours include Morning Exercise, History and Architecture, and a Gourmet Progressive Dinner.

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