We don't know much about Sherborne, but have a DS at Wincoll and we are very satisfied with the school so far. He did really well on his exams and interviews, and was delighted and felt really lucky to have received several offers from several academic boarding schools in the South-East.
We chose Winchester College due to what we perceived to be a certain warmth and camaraderie amongst the boys, something that we haven't really experienced elsewhere. There is a certain tranquility about the location already, and I think it somehow continues in the inner life of the school and manifests itself as what I can best describe as effortless gentlemanly attitude, which we admired considering the strong academic pedigree of the school.
So far we can report excellent food and teaching, and the boys in my son's dorm and clubs are all kind and motivated, at least when compared with my DS' previous school. There is also an abundance of character, which is so rare amongst teenage boys these days, and my DS always sounds content and confident when we talk.
Food is actually surprisingly good, more like a 5* hotel according to DS. Living quarters do vary from house to house, some are reminiscent of an upmarket country/yacht club, others are decidedly a lot more spartan, depending on the character of the house. The water blocks and study quarters were well kept and and sparkling clean in every house we went to, but some of the dorm furniture is indeed a bit worn. We glanced over this, prioritising the human element (housemaster, matron, tutors, character of the boys in the house and the wider school, etc) and the general attitude on campus.
We are still several years from university admissions, but I am also hearing rumours that for US university admissions, a single person supports 140 pupils in a year, which is indeed a bit lean and could be beefed up. Somehow Wincoll still manages to send pupils to Harvard, Yale and other Ivys every year (maybe it could be more with better support) so the pedigree is definitely there. Really hard for me to imagine tutoring at Wincoll, there is neither the space nor the time (boys are very busy, going from club-to-club in their free periods) nor the need for it in my view. Every boy has a tutor (Wincoll staff, mind you) at Winchester, they meet twice a week and that is more than enough at this age. DS never tutored outside school, and we don't plan to start now. The other boys also seem effortlessly bright and motivated/independent enough.
Re pastoral care, we kicked the tires in the first few weeks already after we heard from DS that another boy on the same roll (different dorm) really oozed negativity in the first few weeks. It made my DS somewhat uncomfortable but he is also fairly robust (this would have been just another thing to deal with in my DS' previous school) but Mr Neg in the other dorm continued his banter and seemed to have upset a good friend of my DS. What I heard was a bit of a no event ("you're dumb" type banter), but in Wincoll's otherwise tranquil and gentlemanly atmosphere it sounded like a big deal. In any case, since we had a catch-up call scheduled with the HM anyways, I decided to kick the tires and called the HM's attention to the poor upset boy in DS' dorm, but I deliberately stopped short of naming the perpetrator to see what happens.
This was four weeks ago, and according to my DS, the perpetrator Mr Neg has been behaving like an angel ever since. No idea what happened after I called the HM's attention to the issue, but pastoral care seems to work its magic behind the scenes. I am sure it also helps that that the boys are fairly intelligent, but I wasn't expecting this level of transformation from a single phone call.
Wincoll really knows what they are doing and so far we are delighted.