Why you should go now: This undiscovered gem of California wine country now has more tasting rooms on its central square than any other town in Sonoma County. Stay on the plaza and you can walk to 38 wine labels. No need to find a designated driver or hire a taxi, which can be pricey in these parts.
Where to stay: Reserve at Hotel Healdsburg (from $385/night), which has mod-luxe rooms and an above-average brunch buffet - complete with a waffle bar - included with your stay. Or book a room at its kid sister h2hotel (from $281/night), an eco-chic resting place where you can start your weekend with yoga and finish it off with amazing garden-to-glass cocktails at Spoonbar, on the ground level. Both hotels have a sizeable lap pool with room to sun, on-site.
While you’re there: Peruse the wares for home and garden in the expansive airy retail areas at SHED, which just won a James Beard Award for Outstanding Restaurant Design. While you're there, refuel at the "fermentation bar" where you can sip on housemade kefir water, kombucha or locally made beer and wine. Afterwards, take your bike for a spin around Healdsburg backroads. Both of the hotels above offer free rentals with your room.
Insider tip: If you're having trouble with dinner reservations at some of Healdsburg's most sought-after spots - like Scopa, Chalkboard or Madrona Manor - sidle up to the bar at Bravas. They've just released a slew of new sherry-based cocktails, perfect for washing down slices of Iberico ham and creamy, crunchy chicken croquetas. - Carolyn Alburger