It’s no secret: Everyone (except Carrie Bradshaw) loves Napa. But what if you could drink more wine, for less money, in a more laid-back setting? Enter Healdsburg, the crown jewel of California’s Sonoma County.
Nestled at the intersection of three separate wine regions, this charming town offers endless tasting opportunities, without Napa’s stuffiness or crowds. And when you’re ready to pretend this isn’t just a wine trip, there’s plenty else to do: Wander the picturesque town square, browse cute boutiques (don’t miss A/Muse’s vibrant home decor or Christy Lynn’s chic clothes), eat your way through farm-to-table spots like Barndiva, hike or bike amid stunning scenery, and relax at a historic mansion turned hotel. Oh, and did we mention it’s basically always sunny?
🍷 Whether you have an encyclopedic knowledge of wine or are still Googling “what are tannins?” prepare to spend at least a day swirling, sniffing, and sipping at local wineries.
A few must-visits: Reeve Wines, a husband-and-wife-run operation popular for its small-batch rieslings and pinot noirs; Jordan Vineyard & Winery, where you can tour the 1,200-acre French-inspired château and taste award-winning chardonnays and cabernet sauvignons with a side of downward dog; and Flowers Vineyards & Winery, which, as the name suggests, is nestled among tranquil gardens and majestic redwood trees. Want to skip the driving? Head to Healdsburg’s Plaza, home to dozens of tasting rooms, including Marine Layer, known for its cool-climate, mineral-driven pours.
⛰️ We fully support a vacation dedicated entirely to eating and drinking — but at some point, you’re going to need to touch grass. When you do, Healdsburg’s outdoor activities won’t disappoint. Kayakers can paddle down the Russian River on a guided tour, bikers will love winding past renowned vineyards, and hikers should hit Foothill Regional Park for nearly seven miles of trails featuring oak woodlands, rolling hillsides, and ridgetop views.
Prefer something gentler? The 155-acre Healdsburg Ridge Open Space Preserve offers spectacular vistas and a potential wildlife sighting or two. And if you want to go full wine country, book a horseback riding tour that overlooks Dry Creek Valley’s lush vineyards — and thankfully, keeps the drinking and riding separate.
🍴 If you’re visiting while the Healdsburg Farmers Market is in season, make a beeline to stock up on cheese, bread, and charcuterie — aka the holy trinity of wine-tasting provisions. For the perfect picnic sandwich, swing by Troubadour and order a jambon au beurre or turkey pesto, all of which come on exceptional house-made sourdough.
In the evening, snag a reservation at The Matheson, known for inventive seasonal dishes (think: beef-cheek lumaconi, roasted celeriac soup) paired with an impressive 80-plus wines by the glass. Or, for something more casual, try Lo & Behold, a local favorite serving Almost Famous Chicken Tendies, matcha fries, and other elevated comfort food.