Four Days in Healdsburg

Come for an extended getaway and get to know Healdsburg and it’s surrounds on an insider’s tour

Wil Matthews
A visit to Sonoma Wine Country is great any time of year. Visiting in the off-season, however—winter and early spring—is perhaps the best time of all, since wineries, restaurants, and hotels tend to be less crowded, the weather is as beautiful as always, and there’s plenty to do. Here’s our insider itinerary for an extended visit to get to know our town and its surroundings during this less-traveled time of year:
Wine Director Erin Miller

Day 1: Getting situated

You’ve arrived. Check in, drop your bags, and relax – then head to the lobby for a tasting tutorial of local wines led by Dry Creek Kitchen Wine Director Erin Miller.
Erin’s a winemaker in her own right and as eloquent as she is knowledgeable. The one-hour tutorial culminates with a three-course dinner, and each course is paired with local wines (of course). At the end of the night, Erin will hand over a customized itinerary for wine tasting in the area based on the preferences you shared throughout the class.
That night, if you aren’t too full, head to Lo & Behold for some craft cocktails by Laura Sanfilippo and Tara Heffernon, legendary local mixologists who got their start at h2’s Spoonbar!

Day 2: Exploring the Valleys

The following morning, dine on HH’s made-to-order breakfast (we love the breakfast tostada, with scrambled eggs, pinto beans, and cabbage slaw.) and head out for a day of wine tasting following the itinerary Erin customized for you the night before.
Dry Creek General Store
If you’re feeling particularly adventuresome, borrow bicycles from the hotel concierge and bike the routes Erin drew up through Dry Creek, Alexander, and Russian River valleys. Whatever your mode of transport, soak up the beautiful views of mustard flowers, daisies, and chamomile carpeting the vineyards, and freesia dotting the hills. Try West Dry Creek Road or head into Alexander Valley just off of 128 for idyllic views and picture-perfect photo ops.
Grab a quick lunch at the Dry Creek General Store, a circa-1881 sandwich shop in the heart of the Dry Creek Valley. For perspective, head out to Lake Sonoma, climb the observation tower, and look east over all of Dry Creek and Alexander valleys.
That evening, plan to end your trek in Geyserville and dine at Diavola Pizzeria. Here, Chef Dino Bugica has put together some of the most unusual flavor combinations for pizzas, but they all work—the Dictator, with short rib, kimchee, and Kewpie mayo, is one of the local favorites. After dinner, saunter down the sidewalk to the Geyserville Gun Club, which isn’t a shooting range (as the name suggests) but instead a hip bar with sassy bartenders and Negronis on tap.
Quail & Condor

Day 3: Healdsburg Immersion

Your third day in Healdsburg is all about town. After a breakfast of pastries from local phnom Quail & Condor bakery, head out on foot for shopping, gallery-hopping and, of course, more wine tasting.
Erickson Fine Art features some of the area's most renowned artists, including Wade Hofer whose paintings adorn the walls and guest rooms of Hotel Healdsburg. Or head to Paul Mahder, whose gallery is the largest in Northern California and features a spectacular moss room.
If you’re more into landscapes, check out the Harris Gallery, where a father-and-son duo show their work in a historic bank building. Don’t miss a sidewalk tasting of their excellent curated collection of wines (with one of the Harris duo if you’re in luck). Their wines are as beautiful as they are delicious, each featuring original art on the bottle.
For your wine country look, stop at Susan Graff for classically elegant fashion, find the ultimate men’s shirt from Outlander, or try on flirty dresses at Tamarind.
Before dinner, head to The Rooftop at Harmon Guest House for some classic craft cocktails and an eagle-eye view of Healdsburg as a whole. The vibe at this open-air rooftop bar is swanky but approachable; many visitors don’t even know it exists unless they know someone or happen upon it. On the way downstairs, check out local artist Jessica Martin’s Histories/Futures mural installation in the hallways. The five 35-foot murals will be up through the end of March.

Day 4: West County Jazz

Grab breakfast for the car, pick up lunch from Troubadour Bread & Sandwiches (the same duo behind Quail & Condor) and spend your last day in Healdsburg exploring the western part of Sonoma County that locals affectionately call “West County”. It’s a place where imaginations run wild.
Armstrong Woods
Just outside of Guernevllle, Armstrong Redwoods State Natural Reserve is a great place to stroll through the giant redwood trees (or amp it up with a rigorous hike).
Further west, on the coast itself, find a pocket beach like Shell Beach, Wright’s Beach, or North Salmon Creek for some time on the sand while you scan wave breaks for whales. If you didn’t bring a sandwich from Troubadour, you can grab lunch in Bodega Bay Harbor. It's still Dungeness crab season and most restaurants (we like Spud Point Crab Company) are selling freshly harvested cooked crab.
Later in the day, back in Healdsburg, check-in at The Spa at Hotel Healdsburg for a lavender peppermint restorative massage to warm up after the coastal chill.Then get decked out for a night on the town.
Start with live jazz at Spirit Bar in the Hotel Healdsburg lobby (live every weekend). Relax with a glass of one of your favorite wines from the weekend and great bites from the bar. And if we don’t have the wine you want by the glass, just let us know. We’ll uncork your favorite bottle to wrap up your Healdsburg getaway.