What’s your pleasure? Cozy inns and memorable meals? Shopping? Wine tasting? You’ll find them all in Healdsburg, a charming and walkable town built around a plaza at the heart of the Russian River Valley. Scores of wineries are within easy striking distance of Healdsburg, but there are so many dog-friendly restaurants and tasting rooms in town (we’re partial to canine-welcoming Spicy Vines and Portalupi right on the square) that you might not even get into your vehicle until it’s time to go home.
Go in fall or winter to score off-season rates and specials at dog-friendly lodging properties such as the Best Western Plus Dry Creek Inn (where dog-friendly, motel-style rooms open onto the parking lot for quick exists with your gotta-go pet), the stylish h2hotel near the downtown plaza, or for a splurge, the Montage Healdsburg. Be sure to call and confirm pet fees and size restrictions before booking.
Dining with Daisy can be a challenge in cool weather, but depending on conditions, she can join you on the patios of popular restaurants such as Healdsburg Bar & Grill, Willi’s Seafood & Raw Bar or Costeaux French Bakery. Be sure to call ahead to see if the patio is open or if a table can be set and a heater lit just for you and yours if needed.
Wherever you stay, be sure to stop by Fideaux for housemade treats and canine accessories, and Your Pets Market for dog food and toys. The hilltop Villa Chanticleer Dog Park, meanwhile, is a great place for your pup to mingle with local four-legged residents and run off steam.