I went on this trip last year - my first time with Just You, and I had a brilliant time!
I am not fit by any means but managed the wine trail walk with no problem thanks to a helpful guide who kept stopping (walk just behind him and you get the rest breaks)
The only thing was time, there is so much fitted in to such a short time you dont get much time to do your own thing and seem to be on the coach for the trip back before you're ready!
We had rain for a day and night (the day of the river cruise so we were confined inside the boat) but it still didn't stop us enjoying ourselves.
We had a mixed age group, mostly women, and all got on really well.
I hope you enjoy it too. This year I am going to do the Italian Cities in May and also South Africa (with my Dad) in September, both with JY.
Lesley