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If you are planning your own trip, then a Tuscany tourism guide would be helpful. The flea markets and streets that have been mentioned above are not open 7 days a week and hence it is important that you know the days they are held.
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Weather is the last thing that you should be concerned about while visiting this place. But if you really want a pleasant climate then springs (April to June) and falls (October to December) is the best time to visit this place. Summers are too hot and winters are cold (you can visit if cold evenings make you happy) and during August, Tuscany stays very crowded.