The Schedule

I have settled on autumn as the best time to ride in Italy:

• Winter is too cold, with snow down most of the Apennine ranges and many hotels and other tourist facilities closed.
• Summer is sometimes quite hot and is peak tourist season making the roads and towns less pleasant.
• Spring takes a long while to get started in a lot of Italy and tourist facilities are often not open.
• Early Autumn is the "goldilocks" with stable weather, facilities open and the holiday crowds back at work.

My plan would be to ride north to south which evens out the weather a little as the north gets cooler. This is also the a great time for festivals in Italy. The Palio della Balestra  in Sansepolcro on the 10thy-12th September is my #1 pick. I was there for the festival in 2014 and had great fun.

Lining this up with the a tentative riding schedule gives:

Bike hire

The plan is to hire ebikes in Roma, transport them to Bologna by train and then afterward transport them back to Roma by train from Lecce.

Before and After

To fit the above schedule, here is the minimum dates for international travel and the arrangements to deal with bikes. These are based on the currently published Qatar flights and contain a little bit of slack...

• 6th September depart SYD 21:10 QR0909
• 7th September arrive FCO 13:50 over night at Roma
• 8th September pick up hire bikes ready to ride, train to Bologna

Return:

• 1st October travel Lecce to Roma, return hire bikes, stay in Roma
• 2nd October free day in Roma, stay in Roma
• 3rd October free day in in Roma, stay in Fiumicino or Roma
• 4th October depart FCO 09:40 QR0116
• 5th October arrive SYD 16:55

Actual flight schedules for participants are published here.