On this two-day tour, start your first morning browsing the food stands at Napa's Oxbow Public Market. Drive north on Highway 29 to Rutherford, where the tour of Inglenook provides a fascinating overview of Napa Valley wine making. Continue north on Highway 29 to St. Helena for lunch at Farmstead at Long Meadow Ranch, then visit Calistoga's over-the-top Castello di Amorosa, off Highway 29, or St. Helena's serene Joseph Phelps Vineyards, off the Silverado Trail.
Check into your lodgings—luxurious Meadowood Napa Valley or pleasantly downscale El Bonita Motel are two good options. Poke around St. Helena's shops until dinner, perhaps at Meadowood or Goose & Gander.
Begin day two enjoying coffee and a pastry at the Model Bakery, then drive south on Highway 29 and east on Rutherford Road to Frog's Leap. Make sure to book the winery's entertaining tour in advance. Return to Highway 29 and drive south, then turn west on Highway 121. Stop for lunch at Boon Fly Café, then continue west on Highway 121 to arts center di Rosa and tour its gardens and galleries. Cross Highway 121 to Domaine Carneros, where you can toast your trip with some sparkling wine.
Start your first day at Joseph Phelps Freestone Vineyards in western Sonoma, in Freestone, tasting cold-climate Chardonnays and Pinot Noirs. From Freestone, head north on Bohemian Highway. At Occidental, turn east on Graton Road to reach Willow Wood Market Cafe, where lunch awaits.
After lunch, drive north on Ross Road and west on Ross Station Road to visit Iron Horse Vineyards, known for its sparkling wines. Afterward, backtrack to Highway 116 and turn north. At Martinelli Road, hang a right to reach Forestville's Hartford Family Winery, producer of acclaimed Chards and Pinots. Splurge on a night's rest at the nearby Farmhouse Inn and dine at its stellar restaurant.
Start day two on Westside Road, tasting at Rochioli, then continue on Westside to West Dry Creek Road and turn north. Turn east at Lambert Bridge Road. Assemble a picnic at Dry Creek General Store, backtrack to West Dry Creek Road, and continue north to Preston of Dry Creek.
Head back on West Dry Creek, and turn east on Yoakim Bridge Road and south on Dry Creek Road. At Lytton Springs Road, make a left to reach Ridge Vineyards. End the day with a Cabernet.