Question about the tours vs following an itinerary in RS books

Yes, I have. Nearly 20 years ago I took the lead in setting up my college's program in Italy and had little knowledge of about it besides traveling there a couple times very briefly. Rick's Italy guide was extremely helpful because he offers specific, practical, easy-to-follow instructions. With so many YouTube videos available and forums like this, it's even easier than it was 20 years ago. Sure--the thought of doing this on your own can be a little scary, but people do it all the time. As a friend of mine once suggested, her modus operandi in life is, "Have a plan and follow the plan." Good advice. Not everything goes according to plan, but having a plan often helps avoid a lot of problems.

I answered on your other question on the tour forum.

I'll add that you don't "have" to do any activity that doesn't interest you. It's tougher on a transit day when you are moving from one location to another on the bus but still it's your choice.

You will just want to let the guide know as well as your "buddies". Rick Steves uses a "buddy system" where by on the first day you choose a buddy - not someone you are traveling with but who will look to see if you are present when the group is ready to leave a location. The guide will call out "buddy check" and You look your buddy in the eye and they look you in the eye as a way of insuring everyone is there. It's a pretty efficient system. Anyway, if you are going to skip an activity you let both the guide and buddies know not to look for you.

I did suggest you might consider doing a RS tour of Italy. I'd mentioned I did the Heart of Italy with my brother, SIL and their 2 adult sons (ages 25 and 20 at the time). The "kiddos" had a wonderful time!

From Amsterdam to Italy you would want to fly, in my opinion. WAY too far on a train. Many people on the forum recommend flying if your train journey is over 6 hours.

I think travel goes best when you choose what you want to see, from a variety of sources. You would definitely not want to pay for a tour and then opt out of things you have paid good money for. Your places are well traveled and not challenging to explore, I think you just need to share specifics so we can see if you are on the right track.
You've got quite a discussion going on your original thread, so I would engage there, and then post your planned itinerary in the General Europe for feedback because it involves several countries.

On our very first trip to Europe I really wanted to do a tour, but our son was 11 so we could only sign up for a family tour which was not quite what I wanted. We ended up doing 5 weeks on our own, but I did use the itineraries of tours and his books and this forum in planning the trip. It was a FANTASTIC trip! With the ages of your son's I would think an independent trip might be better (I've only done one RS tour and loved it).

I would encourage you to try planning on your own!

The HUGE benefit to a tour, that is often undervalued by those who don't do the trip planning, is that the trip planner gets to actually be on vacation too. As the trip planner of my family (though my daughter is also a planner :)), I have found over the years that I wasn't really relaxing fully on vacation because part of my brain was involved in what we needed to do 'next'. While I have zero experience with a fully supported tour like Rick Steves, our last trip to Italy and this trip will be partly using a self-guided walking tour that has been arranged by a travel agency (InnTravel for those who are interested). The logistics are all taken care of -- as the planner I don't need to at all think about what's next and plan where to be/when, etc. That has all been done for us, but still with plenty of personal freedom to do and stop wherever we want on a given day.

So I totally hear you on wanting to accommodate the 'kids' (we're traveling this year with the 24 and 20 year old 'kids') and yet I think there's benefit for accommodating YOU too. I felt some guilt for having part of our trip planned out with parts the kids might not like. But also too bad -- they are adults and can decide for themselves if they want to do something or not. :) Yes you can do it cheaper on your own and tailor it to exactly what everyone wants all the time. But there is a cost to that -- not a negative cost necessarily, but a cost.