Just got back from a month in Italy, 2 weeks traveling w/ my wife, and 2 weeks on my bike, touring Umbria, Le Marche (Gubbio, Spello, Monte Sibillini, Ascoli Piceno) and Basilicata (Venosa, Melfi, Matera), about 800 K in all. Since this forum was so helpful in planning my trip I thought I’d share a few insights from my trip. Rather than give a daily account of my trip I thought it would be more helpful to address, in hindsight, some of the questions I had before I left, and what I learned during my trip. Fell free to chime in and add your own two cents.

1. Go!! Italy is a biking paradise – ancient hilltop towns, olive groves, vineyards, good food, good wine, great roads and scenery. Take your best shot at planning, but don’t sweat all the details – It’s pretty easy to find just about anything you need in Italy.
2. Itineraries Vs. – Winging It. I really wasn’t sure whether to stick to a pre-planned itinerary from a guidebook or just completely make up my route as I went. If you’ve never been to Italy and are not fluent in Italian I’d recommend starting with pre-planned itineraries – they have a lot of details figured out for you such as scenic routes with limited traffic, elevation profiles, good towns to lodge and eat in, and hazards to avoid, such as excess traffic or long tunnels. If you’ve never been and don’t speak Italian you’ll be plenty busy figuring things out like traffic signs, how to ask directions, dealing with lodging & meals, weather, etc, you don’t want to be wondering about the rest of the logistics I mention above as well. I used the new Lonely Planet “Italy by Bike” book and brought along the Touring Club Italiano maps for the specific areas I was biking in. Once you get your bearings you’ll be able to wing it more and improvise if you want to. What turned out to be very helpful was a guidebook specific to the region of Umbra and Le Marche – it had detailed info not available in a country wide guide that I used to improvise and modify my trip – I stayed in different towns and took some interesting side trips based in info in the regional guide.
3. Tent and Camping gear? Not worth it, in my opinion. I schlepped a 1-person tent, sleeping pad, stove and sleeping bag around to whole damn time and barely used them (didn’t use the tent or sleeping pad once). Which brings me to my next lesson:
4. Don’t Carry too Much Weight (duh!). The camping equipment really made my load heavy. It wasn’t such a big deal when riding, even up steep grades. The real hassle came when I had to carry my gear onto or off of trains making connections etc., which was miserable. Do your best to limit your load, it will make your experience a lot more pleasant.
5. Bringing your Bike on the Trains – Yes, you can bring your bike on the train, but only the regional trains (not the direct and first class trains), and the longer the distance and the more remote your destination the more critical planning becomes. My first long train ride I was just winging it and showed up at the station early in the morning, going from Ascoli Piceno to a small town in Basilicata – it ended up taking me 14 hours and a lot of grief due to long layovers and missed connections. Going from Basilicata to Rome was much smoother. For one, it’s easier when you’re heading to a large city, like Rome, as there are more direct routes running at more frequent intervals. Also, I researched schedules ahead of time, pre-purchased my ticket. The longer your train ride and the more remote your destination, the more important planning becomes.
6. Rome by Bike? I was a bit intimidated about bringing my bike to Rome. It turned out to be great, but I learned some valuable lessons: It’s easy to catch a train to Rome, however, the neighborhood around the train terminal is infested with seedy, over-priced hotels, so do your homework. I recommend avoiding the low cost hostels like the plague – DON”T stay at the Pop Inn Hostel http://www.popinnhostel.com/ – I made a reservation for a dorm bed for one night because it was the only place available. When I showed up they informed me there was an age limit to the dorm rooms (I’m 48 years old) , so instead of charging me 22 Euro for a dorm room they charged me 69 for a private room. That would have been OK, except that it the floor was gross and sticky and the toilets didn’t flush and the place was just plain gross, I diodn;t even want to take a shower. Do some research and find a decent place. I can recommend Papa Germanos on Via Calatafimi, 14/a Tel ) +39 06 486 919 http://www.hotelpapagermano.com/ just a few blocks north of the train station. Nice place, good people, reasonably priced, great location, there’s even a decent restaurant right across the street, in a neighborhood where most of the restaurants are crappy. Though you have to be cautious, you can bike in Rome and enjoy it, best time is Sunday AM, or late in t the evenings. If you’re not comfortable with city riding then don’t do it.
7. Italian – Get the Collins Gem Italian Dictionary, a small, green cover. Unless you’re fluent you’ll need a dictionary, and this one is not only small and portable (it really fits into your pocket), it’s excellent. Amazing how much info they cram into this tiny book!