Overnight between Healdsburg and Carmel?
 

Already have time planned in San Francisco. Is there another area worth visiting and staying the night on my drive from Healdsburg to Carmel?

Not knowing the rest of your itinerary - the two places that come to mind would be either Half Moon Bay/Pacifica or Santa Cruz. But by the time you got to SantaCruz/Capitola you'd be most of the way to Carmel.

If you want a stop over enroute - Half Moon Bay would be my 1st choice.

Half Moon Bay would be my choice. Although, Healdsburg to Carmel is probably 3 1/2 to 4 hours (maybe slightly more with traffic). You could add on a night to Carmel, and not stop for an overnight.

If you can afford the Ritz in Half Moon Bay, that would be a great idea. Otherwise, I would stay overnite in SF and then head to Carmel. It's an easy 2.5 hours.

Our itinerary is San Francisco, Healdsburg and Carmel. We're going in that order so we can get the hotels that we want. I realize that it's not the most efficient for driving. Half Moon Bay looks beautiful. Maybe we'll treat ourselves to one night at the Ritz.