Having done this drive myself about 20 years ago, I looked forward to the hop from San Simeon to Monterey as the most spectacular scenery. I was not disappointed!
We followed Highway #1 up, with the first stop being Carmel-by-the-Sea. It is partially famous because Clint Eastwood was the mayor for a while a few years back.
Carmel is a trendy and VERY expensive town, with the center 10 square blocks of so filled with shops and art galleries, literally side by side. An incredible number of quality, eclectic little places on beautifully kept heritage streets. The surrounding area is qaint residentials, with a small two story home on a 50×80 lot selling for 1.5 to 3.5 million US (yes, that is million). One place we say was listed at $15M. Incredible, but lovely to walk and drive through.
Many unusual specialty shops. Lynette bought a lovely music box shaped as a guitar.
We had an enjoyable afternoon wandering about. When is came time to eat we wisely consult and elderly local, who directed us to a quaint grocery that make lunches for a fraction of the cost at the adjacent trendy places. Once again, encountering the locals is the best move, and the most fun.
We ended by seeing Carmel beach, and then heading out for our hotel that night in Monterey, just a couple of miles up the highway.