Join Date: Jul 2012
Location: Perth, Western Australia
Bikes: 2015 Apollo Syncro tandem, 2006 Scott CR1 SL (still a beastie race bike), 1993 Trek T200, 2006 Fuji Absolute Le, 2000 Thorn Club Tour
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I was there in June 2008 on the single touring bike with full camping gear. I left the cardboard box in arrivals (may still be there, was very run down then, can't imagine they've invested much since).
There is a train from the airport to Termini. Rome is fascinating if you have even a tiny sense of history, but coffee (invariably excellent) can be expensive. Dining out is easy, enjoyable and good value. Breakfast is pretty thin in Italy when compared to what most Aussie cyclists would expect. Cheap hotels normally have tiny rooms compared to hotels in N America and may struggle to accommodate a fully assembled road tandem, check ahead if you can.
I took a cheap, easy train from Termini to Viterbo and rode up to Tuscany from there. The traffic is terrible but improves a bit as you get into Tuscany. Drivers everywhere are skillful, and seem happy to see cyclists, but most drive very fast, and traffic can be very dense in some areas. I found navigation very challenging during my three weeks in Italy, especially compared to France or Switzerland, perhaps GPS would help. Otherwise: Michelin maps. Roads are mostly good, but smaller roads in rural areas vary a lot. Grades are often steep - the road takes a direct route over a ridge or hill to get to the next town - but distances are not long. Lots of campsites if that's what you want, but they are expensive (especially compared to rural France) because privately run.
In Umbria I visited Orvieto and Perugia. I found that the old towns are on top of steep hills (well worth it though), the newer sections are built at the bottom. Nearly always the campsite is in the newer section, and finding it often proved very tough after a long hot day on the road.
The strade bianchi around Siena are very nice. Siena is very nice, but I only stayed one night. I would prefer a week or two to explore the city and surrounds, it would be a good family holiday one day.
I learned to avoid bigger cities in Italy on the touring bike (the traffic wasn't worth it) while the smaller towns are mostly lovely. The countryside is mostly quite spectacular but is marred by oddly sited factories etc, and I was surprised by the amount of litter on the side of the road.
The Great Lakes are very nice, lots of mosquitoes depending on the weather, and heavy traffic on the Italian side (not so much on the Swiss side).
Italians are very nice.
Lots of info on websites like crazyguyonabike.com, trento bike pages etc. Lonely Planet has a book about cycling in Italy, well worth the price (might even be able to get it as an ebook and save some weight).
Enjoy your trip.