I have done 3 of the My Way Rick Steve's (RS) Tours, Italy 2014, Alpine 2016, Spain 2018. The initial greet and meet get together is normally 1 hour or so, pretty low key. Depending on the tour guide or manager they might have some "drinks" available, wine or beer or other sodas. Normally you go around the room and tell something about yourself, where you are from etc. and if you have been on other RS Tours, it is up to you to say whatever you want. After the meet and greet, you are free to go and do whatever you want that evening. Some tours may take you out on a orientation tour.
On my first My Way tour, after our meet and great, I was in the lobby in our Venice Hotel around 6-7 PM having a beer, another couple from our tour showed up, along with another women from our group, we decided to go out and have dinner at the restaurant the couple recommended, only later did we find out we all lived in the same town, Portland Oregon. Go figure! Both the My Way and guided RS tours give you plenty of time to be with others in your tour group and also to go out on your own and do whatever you want by yourselves. There is nothing wrong with trying to plan every moment of your tour and trying to see every possible site, but it is also great to not plan so much of anything and let fate take you to places you have never imagined. You will have fun either way, so don't stress out about it. The RS tours are well organized and let you enjoy the best. Have fun! Scott