For medieval play, my vote goes to Windenburg, Henford, Forgotten Hollow AND the uninhabited Island on Sulani!
The Crumbling Isle and the northern district in Windenburg work great for huge castles and taverns. I avoid the modern district altogether. Most of my Lords and Ladies live in Windenburg, whereas in Henford is where all me lovely commoners and some bog witches reside. I have pirates and medieval merfolk in (googles) Mua Pel'am in Sulani and then there's Forgotten Hollow where the Hunters live. Hunters as in, pale looking Sims with fangs and also those that are extremely hairy with claws.