Winchester has a very interesting age demographic. It is inhabited almost entirely by students and OAPs and so people tend to fall into 13-21 or 60+. This has interesting affects on, for example, the driving, as I'm sure you imagine. Any money that museums feel they miss out on, charging the inhabitants concessions at either end, is certainly made up for by the hordes of grockles who flock in surprisingly large numbers to the town to view:

The Cathedral . This is very pretty. The architecture is simple and aesthetically pleasing, the building is well heated and tourist-friendly. As worth a visit as most other large-scale cathedrals. Alledged to contain the bone of William Rufus in one of those little boxes you can see around the lower altar.

The Round Table . Whilst this is very evidently not what it purports to be- King Arthur's Round Table-, that is also why it is of great interest as one of the first recorded 'relics' still in existence created solely for the purpose of gathering revenue from eager Pilgrims. Now old enough to merit a visit for 'genuine' reasons, this is an aged piece of the history of exploitation.

Winchester College . This, again, is old and pretty. It is full of little boys at varying stages of cuteness. It is very nice. It does have an attractive chapel, the oldest schoolroom in England and one of two chapels within a cloister in the country. There are two cloisters, two chapels, five or six courts, flinted or otherwise, and an alarming 700 snobs. Ew.

82 pubs . The appeal of this is failry evident. Even the tourists appreciate the benefits of there being so many watering holes. All those 'supervised' school trips.

Ancient Capital of Britain . I don't personally see why that's a big draw, but..

Gurkha Regimental Museum, Hampshire Regiment Museum, The Light Infantry Museum, some 3rd rate Roman remains, The Royal Green Jackets museum, and the an old palace in a state of grave disrepair...

The gist of is that whilst it's doubtless very pleasant to visit for a day, but a diverting place to live for 5 years it is not .