If you're based in Healdsburg and want to take a scenic day drive, the Alexander Valley is a good bet. It's not touristy at all, the driving is easy and you'll see the best of rural Sonoma County. And of course, there are plenty of tasting and shopping opps along the way.
Treat yourself to breakfast at Costeaux Bakery (417 Healdsburg Ave., (707) 433-1913) in Healdsburg, and then start your drive traveling north along Healdsburg Avenue. After passing Simi Winery, turn right onto Highway 128, aka Alexander Valley Road. About a mile down the road, you'll see the gates to Jordan Winery on the right. Continuing on, you'll cross over the Russian River and the valley opens up to gorgeous views of rambling vines.
At the first and only stop sign in the Alexander Valley, you can turn left to follow 128 to Geyserville, but should keep going straight to Jimtown. Jimtown once had a post office and legal identity, but is now just a modern general store. It's a perfect stop for lunch or picnic supplies; try the baked egg sandwich and bread pudding. If your name happens to be "Jim", sign the shop's autograph hound and become part of Jimtown's legend.
On down the road past Jimtown, you'll come to another fork; take a right (hwy 128) and drive along the valley, where you'll see Hanna and FieldStone wineries. Hanna has won lots of awards at the local Harvest Fair and FieldStone (dug into a hill and constructed of old stone, duh) is a good place to eat that picnic from Jimtown.
Keep driving along Route 128, around another bend, and bear right onto Chalk Hill Road. Beware of bikers (the lycra-wearing pedalers) on this route. Soon, you'll see the fancy stucco columns and entrance to Lancaster Estate winery (tours by appointment). At the top of the second big hill, look for the whitish volcanic rock that gives "Chalk" Hill Valley its name, and of course, its distinctive white wines. The largest and most famous winery, Chalk Hill, produces award winning wine season after season.
On Chalk Hill Road, head back to Jimtown to continue the journey. From Jimtown, the scenic option to Geyserville is on Red Vinery Road. If you're pressed for time, take 128 instead, which will lead you past River Rock Casino (pass quickly) and into Geyserville.
If you choose a western route out of Healdsburg, don’t miss Hop Kiln, located on Healdsburg’s Westside Road (#6050, 707/433-6491) in the heart of the Russian River Valley. Hop Kiln is not only one of the area’s most picturesque wineries, but also produces some of the county’s best wines. There is a much photographed building, famous in many architectural magazines and a landmark for in-the-know- design freaks. Inside, the tasting room is as wide open as a bard, and filled with not only wines, but zillions of specialty goods and gourmet foods. Hop Kiln is famous for their Zinfandel infused mustard and the gif balsamic vinegar is thick and sensational.