You are going to Italy when the whole country goes on holiday and when much of northern Europe comes south to play. So getting lodgings is going to be tough. You need to look at hostels and monesteries (if you have any catholic priests in the family you may get an in at the Inn )

Have a look at thorn tree for hostel ideas or book hotels now, using something like booking.com or tripadvisor. There are B&Bs and rooms to let in Italy but it is not very developed. If you want to eat cheaply you can get meals at the back of bars in smaller towns (the meal of the day) M-F for not too much and that normally includes wine but not water. You are going to need a touch of italian for this but not much.

Getting between cities you should use the fabulous train system, book early to get the best prices, you book on line at trenitalia

If I was doing this crazy thing I would make it easier on myself by moving away from the tourist hot spots (which is hhat you have in your list) and look at the second tier cities, like Bologna, Padua, Sienna, Soave, Vicenza, Genoa, Lucca, Bergamo and the other older university towns so there is still some life left in them.

If you want to go south I'd cut out Naples (same reason as too busy) and look at (well it is hard to say as guess where the Northern Italians go on holiday) maybe Lecce/Bari/Brindisi just to say you have been there (no I think I'd stay north).

Good luck, come back and tell us what you decide.

It's a newbie without a clue. Only post, member since June 2012.

bilboburglar - when do we see this person again, if ever?

I've seen over 20 newbies/shills this month alone, and it's only the 11th.

Everybody's a newbie when they first join, and many people don't join until they're planning a trip. "When do we see this person again, if ever?" Well, if they're dissed in the second reply, maybe never.

56Beechwood, although you have little time to ponder, you should seriously consider bilboburgler's suggestions. University towns in particular would be good destinations in August. If your budget is really tight, think about not moving around so much. Moving costs money. If you stay longer in a place, you may also find apartments a good option. Unless you handle heat and humidity well, you may find it hard to maintain a go-go pace day after day for 2-3 weeks.

But you need to finalize and book this trip soon.

A few links that may be of help:

http://www.fsitaliane.it/homepage_en.html

http://www.venere.com/

http://www.cross-pollinate.com/

Rastagyy - what on earth do you have against newbies? Everyone is a newbie at some point...perhaps you could lend them a hand rather then posting on every newbie post calling them shills?

Welcome 56beechwood - don't let a couple rude posters put you off, most of us want to help!

Thanks all for the advice!

I will check the trenitalia website and start looking at hotels as I think we underestimated just how busy it would be.

Thanks for recommending some other places to visit that may be less busy, will definitely give these a look.

Will let you know what we decide on!

I actually don't think your itinerary sounds that crazy at all. You've mostly got at least 3 nights in each place. I wouldn't choose August because it is hot but we can't always choose when to take holidays.

When travelling from town to town in Italy, trains are the best mode of transport.

I didn't quite understand the comment that there will be hardly any accommodation available but visit other towns 'so there is still some life left in them'. I'm sure there is some logic there but it sounds contradictory. Is it that hoteliers go away and close up? I certainly agree that you may get a more authentic feel of Italy staying in less touristed towns. However, all the towns you've picked are famous for good reason!

If you can add another place to stay, I would choose somewhere in the country, as all the places you've mentioned are towns/cities. Perhaps somewhere in Tuscany or Umbria or up in the Dolomites? There's no shortage of villages to choose!

Have fun!

Rastaguy, I don't know why you should assume that someone new is wasting your time. Just don't respond if you feel that way.

Your first itinerary sounded fine to me. Just because it's tourist season there is no reason to ignore the major sights that people come from around the world to see. If you want to change out to see a couple of small, quieter places, that's fine. But IMHO visiting Italy and not seeing Rome - which ruled the western world for a millennium is close to madness.

For the most reliable budget info go to a Let's Go student guide or the Thorn Tree section of the Lonely Planet website. Agree not to underestimate the heat and humidity though - it can be upper 90s and high humidity for days at a time - so I would book only places with good AC to sleep (since many modest restaurants and shops won't have any).

I agree with Dreamon and Nytraveler; even in August, for the first trip to Italy I would select the major sights: Venice, Florence, Rome.

So your initial itinerary seems OK to me. I think that you will arrive in Milan and will leave from Rome, isn't?

Between them it is very easy and not expensive to go by train. Just buy all your train tickets in Milan. Make a list with trains and dates (see wwww.trenitalia.com) and give to the person who sell tickets in Milan train station (or, I heard that it is possible to buy them at a local agency in Milan paying a small fee but skipping the lines.)

Jsut because your itinerary includes big cities, I would use the second day in Milan to make a day trip to one of the lakes (Como or Maggiore). The beautiful landscapes, gardens, lake will make your day! By the way, also this trip can be done by train.
Or, from airport you can go directly to Stresa (Lake Maggiore), stay there for 2 nights and visit Milan as a half day trip from there.

Any case, enjoy Italy!

I think your original itinerary looks fine. I agree that a place in the country might be a nice change from all the cities you have on your list. Look at Orvieto, Sienna and Lucca.

Get advance, timed tickets for anything you can. August is the height of tourist season and everything will be crowded. The lines for tickets will be long.