Very nice town. Great christmas market in the precincts of the cathedral. Need transport to get out and about the local area as you'll exhaust the delights of Winchester in a couple of days. Easy to get to Southampton and the New Forest.
Went there years ago, very nice, but it was only for a 4 day break. Stayed in the hotel at Marwell Zoo, and the zoo is definitely worth a visit if the weather is dry.
My brother lives there and last year he took me to Winchester City FC for the big game against Horndean. It was hilarious. You've got to go if there's a game on. Guy Butters was manager, and probably still is. That afternoon he managed to epitomise pretty much everything that's wrong with football and in fact society. Stand between the two dugouts and just enjoy the 'banter'.
Used to see a bird from Winchester a few years back so was over that was a fair bit, it's a decent town but not a great deal to do there apart from Eating and Drinking really.
couple of really good pub/restaurants couple of miles outside town. Can't remember their names could find out if your interested. Stayed there on way to Bournemouth and Exeter last year. about alf way and made weekends of them.
went for a weekend and liked it. lots of museums - if you're into military stuff there seems to be a museum for each of the regiments that are based there. Good indian there too not sure what it was called though. Trip Advisor was fairly accurate though for the restaurants we went to.
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Ideally we would like to go broadstairs as we usually do every year but its getting harder find somewhere each year!