The big label posh shops are on and arond via de’ Fossi, or there are areas like Santo Spirito (over the river) that has some nice smaller places (good little bars and places to eat too, the Santo Bevitore is great, on via Santo Spirito). San Niccolo, the other side of the Ponte Vecchio from Santo Spirito (but on the same side of the river) is another good spot for bar-hopping, there are a couple of places around via dei Renai (Zoe, High Bar) and Piazza G Poggi (can’t remember any of the frickin’ names, sorry). le Volpi e l'Uva on Piazza dei Rossi, which is a tiny square next to Piazza Santa Felicita, is great, really small and well worth seeking out. It’s a good idea to let yourself get lost around back streets in the centro, it’s very easy to find yourself back on the main drags again. Try and avoid having a coffee/beer out on one of the larger piazzas like Repubblica or della Signoria. My sister was over recently with her five-year-old, who insisted on sitting at a table. Cost 21 euros for two cups of tea and a coke. Be warned, Florence is the city of the five-euro pint and some of the pubs here are absolute stinkers. The Fiddler’s Elbow, on Piazza Santa Maria Novella, is the best (slightly cheaper ale, too). I have to be honest, I spend most of my time sitting in scruffy bars necking back glasses of red wine. They love their vino here, it’s like Bordeaux or somewhere, very proud of their local grapes. A really famous old place is the Cantinetta dei Verrazzano, on via dei Tavolini (just off via de Calzaiuoli, runs parallel with piazza della Repubblica. If you want to go somewhere to eat which isn’t too expensive and not full of braying Brits, Gastone, on via Matteo Palmieri, is great. If the lovely Natalia’s in that night, say you’re a mate of [fulmine's]. I dunno, she might slip you an extra glass of wine or something. Also the Golden View (sounds like a Chinese, but isn’t), which is just by the Ponte Vecchio, overlooking river. Bit pricey, but can be great at night.
I love Livorno, a real shit-kicking, hairy-arsed port. Very Tuscan, everyone loves a good row (politics, football) over a glass of red wine and a nice bit of cake. And they’ve just been promoted back to Serie A. Can’t remember any names, but there’s an area where the canal/river winds it way through the centro and there are all these bars dotted around, it’s great at night, you can’t go wrong wherever you end up, really. It’s a very small centre so difficult to get yourself lost. Shops are shite, mind. Very few Brits-in-sandals too (whenever I’m in the UK, I fly back to Pisa from Gatwick on this BA flight; like the middle-class-wanker-express... one of the few pleasures is when they all gaze out of the window and go ‘oooh, Tuscany...oh... oh Christ, what’s that?’ as they look down on Livorno’s industrial plants and belching fumes).
If you want the full-on Chianti experience (and it can be breathtaking stuff) all rolling hills and sun-kissed vineyards ,try a visit to San Gimignano and surrounding area. I think there’s a regular train service over to there, or a car/bus trip would be nice. Castellina, down towards Siena, is another nice little spot; all you can really do in places like these is sit and get slowly sloshed while watching the world go by. Which is pretty much what you want from a holiday, I suppose.
Places like Siena and Prato (which is so close to Florence it’s pretty much part of the city) are very nice, but bit quiet. They tend to get over-run by tourists at this time of year, too. Pisa’s a bit bloody dull, really and seems to be totally based around the tower. Infuriating, any time you ask a local something they’ll just immediately point the way down the road towards the tower, assuming that’s what you’re after. Lucca, out of all the small historic towns, is probably the one to go for. Gorgeous centre and chatty locals, etc. Not too far from Florence, either. Viareggio, which is about 15 minutes from Pisa, is a typical seaside town, not a great beach though. Very odd mix of seaside shops selling plastic footballs, etc bang next door to some exclusive Prada store, etc. Good place if you like boats too, big old marina. Had some not-bad fish and chips there once.