The History: To many people, Sonoma—just 45 miles from San Francisco—means wine. But when you drink in the surroundings on the eight-acre Sonoma Plaza—the state’s largest plaza—it’s hard to ignore the area’s non-vine history. The park itself was designed 150 years ago by Mariano Vallejo, a military commander and politician who helped transition the Mexican territory of Alta California to the U.S. state we know today. The white, low-rise Mission San Francisco Solano, which borders the park, is even older, dating to 1823; the barracks that housed Mexican soldiers date to 1834. Don’t miss the dramatic stone façade of City Hall, in the middle of the park, dedicated in 1908 and still in use today.
Where to Play: This is the birthplace of California wine, after all, so you’d expect tasting rooms galore—and you’ll find more than 25 of them in the area, including the intimate tasting room of Walt Wines. But there’s more to do than sip. Relive a bygone era in a different way with retro toys, games, T-shirts, and candies at Tiddle E. Winks Vintage 5 & Dime. And stay at the Ledson Hotel, built by a fifth-generation Sonoma farmer and winemaker.