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Let’s face it: Most wouldn’t turn down a trip to Florence just because it’s raining or hot.
But having said that, some seasons are better than others for visiting Florence. Most say Florence is at its best in the spring, when it’s relatively warm but not too hot. In March you'll find it cooler, but you can enjoy a less busy Florence than during the rest of the warmer months. March-April can often be rainy, so dress in layers and be prepared for some spring showers. While in May it really starts to get warm!
Summers in Florence are very hot and quite humid. Daily highs in July and August average 90 degrees F, or in the 30s C. Be sure to bring a hat and periodically dip into stores and cafes to drink plenty of water if you get too hot while sightseeing. Summer is also the busiest season - from June to September (inclusive) expect crowds, long lines, higher hotel rates and plenty of tourists! It is also the nicest time of year to enjoy warm evenings sitting out in a piazza or long walks along the river and there are plenty of concerts, special events and festivals going on. In August, the locals flock to the sea, leaving much of the city empty, but while some restaurants and shops will close for the month, it's probably the most pleasant month of the summer to visit Florence.
Autumn is lovely in Florence, and a good season to be here if you like food and wine. Nothing better than a nice big glass of Chianti to warm you up on an autumn night! The streets and museums are quieter, there's still a fair amount of light for sightseeing and it's not yet too cold.
You say winter is your vacation season? Florence offers you a fair amount of rain but not too much cold. Lows go only as low as the mid to high 30s F, and during the day you can enjoy highs in the mid-50s F. You could pack a coat, but a lightweight jacket or trench might work better, and lighten your load to boot. Layering is the key! Hats, scarves and gloves are favourite local accessories for a good reason.
A good local online weather report is this one, which even lets you check up to 2 weeks in advance: http://www.ilmeteo.it