Tree lined street in Healdsburg, CA
Its culinary experiences and boutique shops set Healdsburg, California apart

48 Hours in Healdsburg, California

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If you're ready to immerse yourself in every aspect of the Wine Country lifestyle, the charming town of Healdsburg has it all - excellent wine, farm-to-table cuisine, interesting history, art of all types, beautiful music, small-town charm, intriguing shopping, and pampering spas.

Getting There

Healdsburg (pop. 11,254) is about a 90-minute drive from San Francisco's Golden Gate Bridge, and you simply go north on the multi-lane US Highway 101 the entire trip.

If you'd prefer flying directly to the heart of Wine Country, four major carriers offer daily flights to Santa Rosa's Charles M. Schulz-Sonoma County Airport (STS), where you can then rent a car, use a taxi or ridesharing service, or take a Sonoma County Transit bus for the approximately 10 mile trip north to Healdsburg.

You can also catch the Airport Express at either San Francisco or Oakland international airports for a ride to STS. And Golden Gate Transit offers bus rides from SF to Healdsburg, a trip that takes about three to four hours.

Once you're in town, here's a quick itinerary outlining just a few of the possibilities for spending a delightful 48 hours in Healdsburg.


Day One


Start the day off right with a delicious Sonoma Wine Country breakfast. Celebrated for its legendary artisan breads, fresh pastries, and yummy café meals, the Costeaux French Bakery has been a Healdsburg institution since 1923; it serves made-to-order bistro cuisine for breakfast and lunch.

Exploring downtown

After breakfast, stroll through Healdsburg’s lovely central plaza, which was named by Travel + Leisure Magazine as one of “America’s Most Beautiful Town Squares.” The plaza’s outdoor bandstand hosts free concerts and other community festivities, and the surrounding neighborhood provides a little something for everyone.

If a bit of retail therapy appeals, the streets around the plaza feature a delightful mix of boutiques and specialty stores. Find that perfect and unique Wine Country gift or souvenir at Mr. Moon’s or Market377. Browse custom handmade furniture, fine décor, and art at the Dovetail Collection. And clothing by designer Yasuko is available in better boutiques nationwide, but in Healdsburg you can visit her only retail store. For more possibilities, check our Shopping & Lifestyle listings and click on Healdsburg.

A shot of the sidewalk and shops in Healdsburg.

If antiquing is what makes your heart go pitty-pat, there are several options within easy walking distance. Mill Street Antiques Plaza houses items from 34 consignors in 15,000 square feet; the Modern Antiquarium collective features a changing array of one-of-a-kind items by 35 vendors; and the 10,000 square feet of space at Antique Harvest is filled with antiques and collectibles.

Downtown Healdsburg is also “Art Central,” with some two dozen galleries located within walking distance of the plaza. Learn more by reading Stroll from Art Gallery to Art Gallery in Healdsburg.

If history sparks your interest, the Healdsburg Museum & Historical Society in a former Carnegie Library building hosts rotating exhibits on local Native Americans and the history of Healdsburg since 1857. There’s also the small but intriguing Hand Fan Museum, which displays both a permanent collection and rotating exhibits, and offers some fans for sale.

Or maybe a bit of personal pampering is more to your liking. A Simple Touch Spa blends ancient healing traditions with the latest advances in modern skin care, or check our Sonoma County Spas & Wellness listings and click on Healdsburg.

Stopping for Lunch

Maybe you’d like to combine a noon-time meal with a bit of relaxation and renewal: at Taste of Tea Japanese Restaurant, Spa and Tasting Bar you can eat traditional Japanese dishes, like Bento boxes or ramen or udon noodles, with a tasting flight of classic teas, and then unwind and soothe with a Japanese green tea foot soak, an aromatic herbal neck wrap, and a tea-infused bamboo fabric facial mask.

Image of cold tapas from Bravas Bar de Tapas.
Bravas Bar de Tapas

Other lunch options include sharing delicious and innovative small plates on the back patio at Bravas Bar de Tapas, named one of the top 20 tapas restaurants in the U.S. by Travel + Leisure; going hyper-local at the celebrated Barndiva, which crafts sumptuous menus with Sonoma County ingredients. Or if a sandwich is what you have in mind, the Oakville Grocery (founded in 1881) creates big, beautiful gourmet sandwiches to order; eat on the dog-friendly patio, soaking up sun while you people watch. 

Time for Tasting

After lunch, it’s time to do what Sonoma County is most famous for — wine tasting. More than two dozen tasting rooms are scattered throughout the downtown area, making it easy to stroll and sip, with no driving required. You can sample wines from well-known wineries or small-production boutique operations, while sitting at a traditional tasting bar, in rustic elegance, or in trendy urban décor. To learn more, read Tasting Rooms for One-Stop Sipping in Healdsburg.

If you want some guidance deciding between the abundance of tasting possibilities, there are several companies providing guided walking tours in downtown Healdsburg. Let’s Go Wine Walk offers a three-hour wine tasting adventure; Savor Healdsburg Food Tours leads a three-hour progressive dining experience; and Healdsburg Wine & Food Walking Tours combines both interests with exclusive wine-and-food pairings, on either a four-hour day tour or a 2.5-hour evening tour.

Perhaps you’d like something sweet to brighten your afternoon. Noble Folk Ice Cream and Pie Bar serves hand-crafted heritage pies and smooth, yummy ice cream.

And for your inner chef, consider taking a class or attending a culinary event at Relish Culinary Adventures. Relish brings together talented chefs and fabulous cuisine at a variety of Sonoma County locations, including its beautiful culinary center in downtown Healdsburg.

Staying the night

There are several options when it’s time to check in and unpack your bags. Enjoy sweeping views ringed by redwood forested mountains at the Raford Inn. Other lodging suggestions within an easy drive include Geyserville's Geyserville Inn, or Old Crocker Inn, in Cloverdale. The town of Windsor offers national-brand hotels: Holiday Inn Express, Holiday Inn Windsor Wine Country, or Hampton Inn & Suites.

Ready to Dine

You’ll need to definitely plan ahead and get advance reservations for dinner at SingleThread restaurant, awarded three Michelin stars in 2019 for its 11-course tasting menu customized to guests' dietary preferences and restrictions.

Shot of food from SingleThread in Healdsburg

But that’s just the start of the outstanding choices for dinner. Savor Yucatan flavors and Sonoma County ingredients made with French finesse at Mateo’s Cocina Latina; enjoy small plates designed for sharing at Willi’s Seafood & Raw Bar, including at least eight varieties of fresh oysters; or check our Guide to Restaurants in Healdsburg


Healdsburg includes several options for enjoying an evening together. On Saturday nights, catch live music at Spicy Vines, a fun and stylish tasting room that offers wine by the glass, a curated flight, paired with small bites, or as craft wine cocktails (dinner can be included at Saturday Night Jive with advance reservations).

Enjoy a classic cocktail or glass of wine, bistro menus, and a classic French supper Sunday evenings at Barndiva Gallery + Bar, which serves as an art gallery by day, but offers dining and drinks at night, Wednesday to Sunday.

Duke’s Spirited Cocktails specializes in amazing craft cocktails made to order, with almost all liquors and bitters made from local Sonoma County products, as well as some ingredients from their own gardens. 

And if you enjoy visiting local watering holes, drop by John & Zeke’s Bar, which includes a pool table and shuffle board.

Day Two


Greet the morning at the Downtown Bakery & Creamery — a local favorite for more than 30 years — with breakfast pastries baked fresh every morning and a café menu on weekends (a recent menu included pancakes, eggs, quiche, breakfast pizza, and more). 

Beignets from the Parish Cafe are covered in powdered sugar in Sonoma County.

Getting Out and About

To get a sense of the delicious abundance available in an around Healdsburg, wander through the Healdsburg Farmers Market, held twice a week from 9 a.m.-12:30 p.m. on Tuesdays, June through September, in the Healdsburg Plaza, and from 8:30 a.m. to noon, mid-April through November, in the parking lot at North and Vine streets, one block west of the Plaza. For more ideas about finding fresh-off-the-farm produce and products, read Healdsburg Farmers Markets and Farms.

To get a close-up look at Sonoma County’s most famous crop, take a self-guided vineyard walk at three area wineries — Amista Vineyards, Francis Ford Coppola Winery, and Mauritson Wines. Part of a program by the Sonoma County Winegrowers association, the trails are no more than a mile long and relatively easy to walk, with signs marking points of interest. When you arrive at each winery, stop in the tasting room to pick up detailed  walking-tour guide. 

If you’d rather travel under your own power, Healdsburg is surrounded by acres of vineyards, rolling hills, stunning vistas, and quiet roadways — which means the area offers gorgeous cycling routes. 

A woman cycles next to vineyards in the summer in Sonoma County
Alexander Valley AVA

Both bike rentals and guided tours are available in Healdsburg through Spoke Folk Cyclery and Getaway Adventures & Rentals, which leads a Healdsburg Sip ‘N Cycle tour. Ace It Bike Tours offers a Healdsburg Wine Country Cycling tour. For even more options, check our listings of all Sonoma County bike rentals and tours.

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.

Or glide away with Segway of Healdsburg, on a guided tour of Russian River Valley wineries and vineyards or Armstrong Redwoods State Natural Reserve. Each tour begins with a 20-minute session on how to safely ride these two-wheeled motorized personal vehicles.

Break for Lunch

When you’re ready for a noontime repast, there are several options. In town and just north of the Healdsburg Plaza, Journeyman Meat Co. is an old world-style butcher shop with a wood fired oven and a simple menu that changes weekly, with items like pizza with roasted leeks, bacon,  and farm egg, or a plate of their house-made salumi with pickled vegies and cheese.

The old country store has a signnpost with winery names on it in Dry Creek Valley, Sonoma County
Dry Creek General Store

If you’re exploring outside of town on Dry Creek Road, the Dry Creek General Store offers handcrafted sandwiches, soups, and salads in its deli, and the store boasts a large selection of local wines.

To the Water

Spend the afternoon relaxing and playing on a riverside beach at Healdsburg Veterans Memorial Beach. From July through Labor Day, a seasonal dam creates a calm swimming area, and lifeguards are on duty daily. There are also picnic areas, lawns, a par course, and restrooms.

Directly across the street, Wicked Slush offers the perfect summertime treats — local organic soft-serve ice cream in 26 different flavors and slushes, which are made of firm but flexible ice in a dozen flavors and styled after slushes from the owner’s north Boston childhood. Try a split — half slush, half soft-serve, with any combination of flavors you choose.

Healdsburg Beach is also the launching point for self-guided half-day and full-day summertime inflatable canoe trips by Russian River Adventures. Paddle and float down a secluded section of the river, with no roads or buildings, watching birds and wildlife as you go, and then ride the shuttle back to your car from the take-out point. Bring a picnic. (Dogs are welcome on full day trips.)

Image of the water of Lake Sonoma with a little fog on it in Sonoma County
Lake Sonoma

Perhaps you prefer a lake to a river. About 20 to 25 miles northwest of Healdsburg, Lake Sonoma offers 2,700 acres of lake surface and 50 miles of shoreline. Surrounded by steep hills and vineyards, the lake was created in 1983 when the Army Corps of Engineers built Warm Springs Dam. Lake Sonoma Marina rents patio, ski, sail, and fishing boats, and offers a barbecue area, a deli, and a swimming beach. The Lake Sonoma Visitors Center & Hatchery offers exhibits on the cultural and natural history of the Dry Creek Valley, campfire programs, Junior Ranger programs, and tours of the fish hatchery.

For another perspective on this beautiful lake, go exploring on the back of a sure-footed horse at the Ranch at Lake Sonoma Horseback Riding. They offer a wilderness experience on horseback just a 15-minute drive from downtown Healdsburg, with incredible scenic views and a variety of trail rides for beginners to adventurous riders.

And of course, it’s a relatively short drive to explore the stunning Pacific Ocean coastline. The Sonoma Coast State Park includes 17 miles of beaches and bluffs stretching from about four miles north of the coastal community of Jenner, where the Russian River joins the ocean, south to Bodega Bay. Highlights include Goat Rock Beach and Bodega Head, but there are all sorts of incredible places to discover on the coast. 

For more ideas of where to go and what to do, read 5 Fun Things to do in Healdsburg, Guide to the Russian River Resort Area, and 12 Tour Ideas for Exploring Sonoma Wine Country.


Once again, there are several delicious options for dinner, depending on your location and mood.

If you spent the afternoon exploring the coast, River’s End Restaurant & Inn in Jenner offers scrumptious food and gorgeous, one-of-a-kind sunset views.

Jenner cliffside looking over the water in Sonoma County.

From Lake Sonoma, make your way to Geyserville for Italian at Catelli’s or Diavola Pizzeria & Salumeria.

And if you’ve made your way back to Healdsburg, Chalkboard Restaurant is a casual contemporary celebration of the best ingredients Sonoma County has to offer, with a daily-changing menu inspired by produce from a dedicated three-acre garden and local farms, paired with local wine flights and inventive cocktails.

Had such a wonderful time in Healdsburg and Sonoma County that you want to extend your stay? Check our listings of Sonoma County Hotels & Lodgings.