It's been 35 years since we were last in Napa/Sonoma so this is like starting over.

We're not high rollers but just overdue for a little wine getaway.

We have one night Brookings, OR, 2 nights Elk Cove Inn, 2 nights at Healdsburg. Then will probably plan one at Calistoga.

To maximize time, what's the best way to loop during our back to back in Healdsburg, then see new things on the day we overnight at Calistoga or St. Helena?

Not sure I understand what you are asking but highway 128 through the beautiful Alexander Valley would be most direct route. There are wineries along the way, you could take a picnic from Oakville Grocery store in Heldsburg and picnic at Hanna Winery, nice folks there. From Calistoga/St. Helena to Healdsburg is not far. If you drove direct maybe an hour, but stop and smell the roses. Stay off 101 at commute time! Hope I helped.

You did help. And, I'm realizing that I didn't ask in the clearest way.

Looks like, however, if distances are that close that 3 nights will give us more than enough time.

You certainly can pick one place to stay and then make day trips. If you stay in Healdsburg, you can easily make a trip to Napa........should you want to.......altho there is so much to see in Sonoma County one really doesn't need to see the "other" valley!! Its an easy loop from Hbg through the Alexander Valley to Calistoga, and then south and eventually west to the town of Sonoma and then up #12 to Santa Rosa and back to Hbg. I wouldn't bother changing hotels....or where ever you are staying.

So many ways you can go if you base in Healdsburg. We like Robert Young and Fieldstone in the Alexander Valley. You could also head up the Dry Creek Valley. Or head down the Eastside or Westside Roads from Healdsburg towards Guerneville. Visit the smaller wineries on the way, check out Korbel on the River Road and the Armstrong Redwoods.