We've been once, right before covid started, did att pro am at pebble and mostly Napa. If you aren't a wine snob you can't really go wrong.
It was the off-season, so reservations weren't required, which was really nice. While we enjoy wine, we also try something new each time so there was no winery we had to go to. My wife is indecisive, so I just picked one as our first stop that was one of the gorgeous stone castles, then from there we literally chose by which ones looked cool to us property wise which led to a hilarious conclusion.
We ended up at rombauer because it's on an steep hill and as we pulled up, realized they had only valet parking so we were like ****, this may be above our league, luckily it was end of day so we didn't have to valet and just walked in. They were out of tastings, but said we could grab a glass at the counter and enjoy the sunset as they had amazing outdoor seating overlooking the valley. So we get to the counter and we order cabs, our preferred drink and the guy was confused, and said everyone comes for their Chardonnay, and we were like meh, we'll still do the cab, we don't love whites. So he ask how we ended up there and we told him it looked cool to drive up the hill they were on. He had absolutely no clue how to respond to that, as he had never encountered someone blindly driving around before clearly. So he gave us a tasting of their Chardonnay insisting we couldn't stop by without trying it. As we chatted, we ended up getting a full tasting from this guy for free as he was having too much fun talking to us/teaching us about their brand since I doubt he ever gets to do that at the outdoor bar counter we were at. We felt obligated to splurge and got their fanciest bottle of cab since we had already got 4+ free drinks, but it was great and we all had fun. Sometimes it pays to be clueless (we were also like 28/30).