Yeah, we went to Napa two years ago and stayed at Boothe State Park. It was 12 hikers from Miami who work together for an airline. Our choice was either a $200-a-room place in Napa or what we opted for, the State Park campground up by Calistoga. We didn’t reserve it, but since it was midweek and not taken, we got the group site, which fit all our tents (eight). I think it came out to about $4 a person a night. And since half of our group was Cuban (a partying bunch), that allowed us to raise hell without making anyone mad since we were isolated from anyone in the regular campsites who might impose on us something called quiet time or whatever.
We did the Mount St. Helena hike the next day, it was cloudless and hot and nearly killed several of our group suffering from hangovers.
We kind of fell into a routine. Hike in the morning and hit the wineries in the afternoon. There are plenty of trails (even up behind Boothe) to keep you busy at least in the morning before you hit the tasting rooms in the afternoon. It is a dichotomy:
getting fit in the morning, then killing brain cells in the afternoon.
On a more personal level, we (two) have hiked in Tuscany doing a backpack trip thru the vineyards of Chiant Classico. We did this on the fly, and slipped the van driver for some high-end organized group a little money to take our packs to the next town along with theirs, allowing us to walk without everything you need in Italy for 3 weeks.
Another hike/wine spot is the Rogue River. We camped in a state park and then hiked all over the place. But we interspersed the hikes with stops at wineries and even the Shakespeare Festival in Medford.
Our next wine-hike is the Skyline to Sea trail near Santa Cruz. A three-day backpack followed by two days at several of the wineries nearby. Endless possibilities.