Welcome to Healdsburg

It all radiates out from Healdsburg Plaza, the town’s sun-dappled central square (bordered by Healdsburg Ave and Center, Matheson and Plaza Sts).

Traffic grinds to a halt on summer weekends, when second-home-owners and tourists jam downtown. Old-timers aren’t happy with the Napa-style gentrification but at least Healdsburg retains its historic look, if not its once-quiet summers. It’s best visited weekdays when you can stroll tree-lined streets, sample locavore cooking and soak up the NorCal flavor.

Top experiences in Healdsburg

Amazing hotels and hostels

We've pre-picked the best hotels, hostels and bed and breakfasts to make your stay as enjoyable as possible.

Healdsburg activities

$164 Day Trips & Excursions

Wine Country Bike Tour and Picnic Lunch from San Francisco

Experience California Wine Country in a fun and exciting way – by bicycle! After complimentary pickup from the James Lick Memorial Statue , escape the hustle and bustle of the city and relax on a scenic drive to Northern California’s famous wine-making region, where you’ll tour several wineries by bike and enjoy a delicious picnic lunch. Explore Napa Valley, Dry Creek Valley or Russian River Valley, depending on the day, and let your local sommelier guide teach you about the unique characteristics of the various regions. Dry Creek includes the town of Healdsburg and is known for its Zinfandel, while Russian River is near Santa Rosa and is known for its Chardonnay and Pinot Noir. Napa Valley includes the hot springs of Calistoga and is a world-renown region for producing several types of premium wines. Take a scenic bicycle tour of the beautiful area and visit hand-selected wineries known to produce some of the highest- quality wine in Northern California. At each winery, taste a variety of local wines and enjoy expert commentary from your sommelier guide. Follow charming roads and enjoy the breathtaking landscape of the California Wine Country as you cycle from winery to winery. Stop between wineries and indulge in a delicious picnic lunch (see itinerary section below for sample menu) among the vineyards. See the Itinerary section below for sample menu to whet your appetite! A shuttle will follow you to carry any wine purchases and assist any riders who would like to be driven. The total mileage ranges between 10 and 15 miles (16 and 20 km). Biking the whole way is optional and, at any point, guests may choose to ride in the shuttle.

$89 Food, Wine & Nightlife

Healdsburg Wine Tasting and Food Pairing Guided Walking Tour

Make your way to Healdsburg Plaza to meet your local guide, a certified tourism ambassador of Sonoma County. Then set off on foot to begin your tasting tour, stopping to sample food and wine at half a dozen hotspots in the historical downtown area.Your first stop is a local bakery (perhaps Costeaux French Bakery & Cafe or Moustache Baked Goods) for samples of fresh-baked artisan bread and other delectable treats.Continue treating your taste buds with a visit to the Russian River Tea Company. Cleanse your palate and sample several freshly made teas, and then stroll over to the Healdsburg General Store or SHED, which serves up farm-to-table gourmet fare. Try an arrangement of unique tastings, and then head to the Williamson Wines tasting room to sip several boutique wines accompanied by creative dishes. Listen to winemakers share their family stories before finishing up your tour at a local winery. Here, enhance your final wine tasting with epicurean delights such as jams, locally crafted artisan cheeses and charcuterie. When your tour ends, you'll be well prepared to continue exploring all that Healdsburg has to offer on your own.Please advise any specific dietary requirements in the "Special Requirements" field at time of booking.

$89 Food, Wine & Nightlife

Healdsburg Small-Group Food and Wine Walking Tour

Meet your guide and small group (no more than eight participants) in downtown Healdsburg, and set off on your 3-hour gastronomic adventure. You'll enjoy tastings at six local spots where you’ll learn about the area’s food and wine culture. Your local foodie guide is a certified tourism ambassador with a vast knowledge of Healdsburg and greater Sonoma County. You won’t just be led from spot to spot — you'll have the chance to meet winemakers and learn how the town's celebrated chefs and business owners have achieved their recognition in the industry. With this insider scoop on one of California wine country’s most-loved destinations, you can leave the tour with a list of more places to check out on your own. This lunchtime tour highlights the Sonoma chefs, winemakers and farmers who are using organic, sustainable and seasonal methods of producing food and wine. Visit a wine boutique to mingle with locals, and meet industry experts and winemakers as you sip a world-class glass of red or white. (A sample list of stops is included in the Itinerary section below.)Your tour ends in downtown Healdsburg in the early afternoon, giving you time to continue your exploration of the town’s shops, restaurants and tasting rooms on your own. Total walking distance is just over a mile (1.6 km).

$50 Food, Wine & Nightlife

Healdsburg Wine-Tasting and Food Pairing at Williamson Wines

Your wine-tasting experience takes place in downtown Healdsburg, a lovely, quaint town in Sonoma County that’s known for its great wines, lovely boutiques, restaurants and bed and breakfasts. In the tasting room of Williamson Wines, let your expert host guide you through the world of California wines as you taste five different wines paired with complementary appetizer food plates. Icon Wine Tasting Perfect for more seasoned wine tasters, the Icon tasting session lets you taste the winery’s most exclusive, exquisite wines. As you sip, learn from your host about how these smaller-production wines are made – with only the best fruit available using the most painstaking winemaking methods to ensure top-notch, unparalleled quality. Produced in smaller quantities and at higher production costs, Icon wines include the more exclusive versions of rosé, chardonnay, sauvignon blanc, pinot noir, cabernet sauvignon and grenach.Enhance the flavors and aromas of these wines by pairing them with the delicious bites listed above, all specially prepared by the in-house chef. The winemaker often joins in on this tasting session, providing a more in-depth and informative experience.

$50 Transfers & Ground Transport

Russian River Canoe Trip from Healdsburg

Hop aboard an inflatable canoe for a fun canoeing adventure! These inflatable canoes are designed to be stable and more comfortable then traditional metal canoes.  These canoes have bench seats and can fit up to 3 adults, or 2 adults and 2 kids.  Dogs are also welcome on board for an additional $10.00 fee per dog.  (FULL-DAY TOUR ONLY) Half-Day Tour:  Once at the Russian River, a RRA river wrangler will set up your canoe and show you the basics of paddling before getting you onto the water and sending you on your way! Settle into your canoe and journey from Memorial Beach to Crow Bar. Take your time as you float lazily along this easy, calm 4-mile (6.5-km) stretch of the Russian River, enjoying views along the way. Stop at any of the pristine beaches, enjoy a picnic lunch, or take a refreshing dip in the water.  (NO DOGS ALLOWED ON HALF DAY TOUR) Full-Day Tour:  Pack a picnic lunch and your favorite beverages and set off down the most secluded and hard-to-access section of the Russian River. At your launching spot at Memorial Beach, board your canoe and embark on your 9-mile (14.5-km) journey along the calm, easy-to-navigate waters to Wohler Bridge. Your RRA river wrangler will set up your canoe and show you the basics of paddling before getting you into the water and sending you on your way. Stop at a pristine location to take a refreshing dip in the water, have a picnic, or just check out the wildlife.  This is a self-guided adventure so stop wherever and whenever you want along the river. At the end of your half-day or full-day excursion, regularly scheduled shuttle vans will bring you back to your car.  Rinse off stations, restrooms and changing stations available for use when you get back.

$204 Day Trips & Excursions

2-Day Alcatraz Admission and Wine Country Bike Tour Combo

Day 1: Wine country bike tourYour 9-hour day trip starts with a drive across the Golden Gate Bridge to Northern California’s renowned wine country. Depending on the day of your tour, you'll explore the wine region of Napa Valley, Dry Creek Valley or Russian River Valley.Dry Creek Valley in Sonoma County includes the town of Healdsburg and is known for its zinfandel; Russian River Valley, near Santa Rosa, boasts distinctive chardonnay and pinot noir; and the world-renowned region of Napa Valley, which includes the hot springs of Calistoga, produces many different high-end wines. By bicycle, follow your guide along scenic roads, stopping at four handpicked wineries known for their quality varietals. Hear about the unique characteristics of each glass you sip from your wine expert guide (tasting fees are at your own expense). Between wineries, pedal past rolling vineyards, and enjoy feeling no guilt about the wine you drink with all the calories you're burning. When your group is ready for lunch, take a break among the vineyards for a gourmet picnic. Your day trip ends with the drive back to San Francisco.Sample lunch menu: Cheese selection: French brie, local goat cheese and Spanish manchego Charcuterie selection: Prosciutto, salami, coppa Fresh locally baked bread Green salad: Wild arugula with fresh figs, roasted asparagus and pine nuts in a Meyer lemon vinaigrette Legume salad: Toasted garbanzo beans with roasted Brussels sprouts and wild mushrooms in a sun-dried tomato rémoulade Grain/starch salad: Arborio rice with roasted butternut squash, charred broccoli and dried cranberries served with shaved parmigiana Day 2: Alcatraz tourMake your own way to Alcatraz Landing at Pier 33 in San Francisco for the 15-minute ferry ride to ‘the Rock,’ aka Alcatraz Island. Snap photos of the Golden Gate Bridge and the city skyline as you cruise across San Francisco Bay. When you arrive, listen to a brief history of Alcatraz and head into the cellblock to start your 2.5-hour audio tour ‘Doing Time.’ Through your provided headphones, hear about notorious gangsters such as Al Capone (Scarface) and Machine Gun Kelly, and learn how several inmates attempted escape. Explore the prison grounds and stay as long as you wish before returning to Pier 33 (ferry departs about every 30 minutes).