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The cycling season in central Italy is basically April through November.
The best months in terms of weather and crowds are May and October. The
average high temperature in Florence in May and October is 75 degrees, the
average low is 52. By July and August the average high climbs to 92
degrees. In the higher elevations of the Apuan and Apennine mountains it
can of course be much cooler. There are ski areas throughout these
mountains and the wild flowers still look fresh in August.
With the warmer mid-summer temperatures come proportionately
larger crowds. The main tourist destinations, such as Florence and Siena,
will be packed. If you want to stay in the hotel of your choice during June,
July, and August, you will have to reserve months ahead of time. By way of
example, I have had trouble reserving a room in January for a July stay in
Florence. Farther off the beaten track there is almost never a need to book
ahead.
With this in mind, if you were to plan an itinerary which included
Florence, Siena, San Gimignano, or some of the other well-known tourist
destinations, you would be better off doing this tour in May or October,
because it will not only be cooler but the crowds will be less, and
accommodations will be easier to find. If you were to plan a tour over the
high passes of the Apennines, you would be better off in July or August
when it will be warmer high in the mountains. This route would be far off
the beaten path, so finding accommodations should not be a problem.
Summers are generally dry in the Tuscany region, but you can always
encounter rain. Rarely will you have more than a day of rain unless you are
particularly unlucky. If it does rain, take a day off the bike, read a book,
write postcards, explore, drink wine with lunch. Wherever you decide to
tour, always factor in a day or two of float time to allow for jet lag, lost
luggage, bad weather, etc.
