>>616741Copy from my reply from other thread.
If you don't mind much about the medieval part;
Fate series, especially fate/zero.
Kara no Kyoukai series, MC uses a short sword. This is anime movies so the art, effect, and sound are great.
Kiseijuu: Sei no Kakuritsu. Good amount of violence but no swords. Nice character development too.
These ones are not about medieval, swords nor violence/gore but they are good anime that fit your 'wisdom moments' I would like to recommend;
Monogatari series. This one is 'mainstream'. It has a lot of development of characters and some 'sexy time'. If you're gonna watch this please note that you will love it or hate it. No in-between.
Clannad and Clannad:After Story. They are love comedy but one of the best of this kind.
Fullmetal Alchemist: Brotherhood. This is 'Top anime of all time' on MyAnimeList and it really suits the title.
Shiki. Horror anime.
Shinsekai Yori. MCs goes from children to adult. Not really medieval but looks like that because it's the post-war time. This one will give you a lot of thing to think.
Steins;Gate. Sci-fi. Time-travel.
Tengen Toppa Gurren Lagann (and its movies). It's very fun action anime. The final parts are epic and very big battles. I repeat, VERY BIG BATTLES.