We were completely under whelmed when we went to the schools open day many moons ago. We knew very well and had visited SPS which I'd tried to hate but loved so what we saw of Winchester on the open day was a complete disappointments. Frankly we only continued with the registration process because I'd arranged to meet a three house masters shortly after the open day and it just seemed sheer bad manners to cancel.
Even after meeting the HM's I was still slightly underwhelmed and SPS with all is logistical difficulties for us seemed like the best option. We even looked at Eton (despite my pathological loathing of ridiculous uniform). Anyway we persevered, took DS back to meet two of the HM's and this time had lunch in one of the houses with the boys. This particular HM wanted us to meet the boys so that we could see how boys from his house turned out. I sat with the U6 th. It was then that the penny started to drop, one boy in particular was just how I imagined my DS would be at this age, his whole way of being, the way he addressed me, his honesty, something I can't quite define. None went into raptures over the school, they were barely even enthusiastic, all talked honestly about it, the dons and the HM, (my DS now says the same thing about him!) the head, but three things came out of it, none wished they'd gone anywhere else, all agreed their HM was the best at choosing 12 boys who will get on and the enormous camaraderie that existed between the 12 of them. We were offered places at both schools and agonised for a whole year, surprisingly it was meeting the head (I'd been unimpressed by him before) on a sunny summer afternoon for the interview you have with him after you've been offered a place that swung it for us. Winchester College was so peaceful and beautiful, the head was gentle and encouraging to my DS, described it as not a school for "tramplers" his prep school had been and he'd hated it, we went home and politely declined the SPS place.
IMO I don't think the boys have any idea how lucky they are and how different the type of education they receive at win Coll is. I recently listened to him discussing his passion for a Shakespeare and one play in particular quoting various lines, debating a particular character with my DH, he quoted lines of poetry when we were talking about a recent conflict in Africa for a non reader this is amazing in our opinion. He talks with enthusiasm about art (always a passion) but a particular style and period discussed in Div, he's never been interested in it before in fact was rather dismissive of it previously and then the wonders the calculus are also mentioned in passing, neither my DH or I get math our eyes glaze over. Oh and much to my husbands delight he's developed an enthusiasm for opera again thanks to the Div don. This for us makes it worth every penny we are not wealthy in the grand scheme of things and live a very normal life we've choose to channel all our spare money into school fees but to hear him talking like this is for us worth every penny we spend on school fees this is what we wanted. Not all are like this many are just normal happy teenagers I don't believe that all bright children are intellectual although I suspect most intellectuals are bright. Neither do at think being intellectual makes you a better person in fact from personal experience I think it makes you a restless person always looking for something else to fill your mind. But if you have an intellectual child then a I personally don't feel they'll get a better education than that which Win Coll offer.
I'm not surprised the boy who showed you round was unenthusiastic, its so easy to take what you have for granted, we live in a very old falling down cottage we have this huge ancient fire place (that actually architecturally incorrect someones fiddled with it) everyone comes in and ooohhhhs and aaahhhs over if I don't even notice it anymore I can only see what wrong with it! The boys live in a privileged bubble, my DS can barely remember not boarding, they are so used to this life, he was surprised when the team from a visiting school started photographing the buildings around college, why would you want to photograph them? A relative was questioning him about boarding recently he couldn't really describe it as he has nothing to compare it against. But as I've recently told him it's not until we loose something that seems unimportant to is do we realise how good it was!
I've met quite a few boys over the last three years I've watched them together as a group, all ages, the enormous camaraderie that I saw at that lunch so long ago is still so obvious and many are like my DS slightly reserved (different from shy), unassuming and self effacing, most when you get to know them better are very sharp and indeed often amusing with a very dry sense of humour, they are also polite, always honest about the school but never all over you like a rash.
There are lots of good schools out there Posadas including Eton which may not be for me but I acknowledge it's a good school and I still believe that SPS is virtually in a league of its own but for us a Winchester has been all the things we hoped it would be and were told it was so very very long ago by the first person who said to us your DS is an intellectual he should go to Winchester. What it doesn't do is shout it from the roof tops. One friend looked at it "I don't like it because I can't see what I'm buying into" I have it on hood authority the school doesn't want those type of parents!
On a Saturday by the way boys are meant to go to a variety of extra curricular activities, sporting or cultural, recently my DS had not done his because he and his friends including of course many in the upper 6th are doing exams so I understand many have not been running. But I know all the rest of the year round he as an individual does his chosen sport on a Saturday afternoon. Do not underestimate how mentally and physically tiring full boarding is, how busy their lives are, many by now are exhausted, especially all those doing public exams, my DS is home tomorrow night he's so tired at times he can barely speak, he'll sleep most of the weekend, many boys just like to just chill out whenever they can. Finally you're right about the houses, many are scruffy, in my DH's house the communal area is tiny the whole house do struggle to fit in, yet he frequently talks about conversations he has with his HM, assistant HM, visiting Dons etc so conversation must take place somewhere. If you want pristine accommodation look at a Eton instead but I personally don't dare it's the people that make a school not the buildings.
Good luck I hope you find somewhere, do PM me if you want to know more.