DS has received 13+ offers from both these schools and we're really struggling to decide between them.
DS is quiet and laid-back, with a quirky sense of humour, interested in lots of things but hasn't really found his passion yet, currently happy but rather bored/not being stretched at his prep school. He's academically strong across all subjects, possibly leaning slightly more towards maths and sciences than humanities. He's only recently discovered an enthusiasm for sport (mainly football) but is philosophical that he's never going to be A team material. He's a bit of an introvert and likes his own company at times, but is mature and rubs along well with most of his classmates and has a small group of good friends. When applying to senior schools, he was adamant that he wanted somewhere very academic, and he achieved offers from both schools without any tutoring.
Because of Covid, we've had limited opportunities to visit either school or meet other prospective students in person, which isn't helping the decision process.
DS's prep school think that Winchester would be a great fit, but find it difficult to give an opinion on St. Paul's because it isn't a common destination for their leavers. DS is worried that Winchester will be full of intense intellectual types who won't like to do "ordinary" things like football or Warhammer (despite knowing older boys from his prep school who have gone to Winchester who aren't like this at all!).
St. Paul's seems to have a pushier, more "corporate" vibe, and I have heard that sporting prowess is a big factor in determining social pecking order. I worry that DS, as a middling sportsman and quieter personality, will get lost in the crowd.
DS doesn't have a clear preference for day vs boarding. Fees at both are just about manageable but a big stretch.; I get the impression that socially this would matter more at St. Paul's than Winchester, but happy to be corrected on that.
If any parents with experience of either school would be willing to share their insights, I'd be very grateful. Really stuck for a decision at the moment!