Hello,

I am planning a trip to Italy in mid-May to early June. Right now, I'm not so sure about the exact duration of the trip but I expect it to be no less than 3 weeks.
I have only started some initial research but I'd like to get some advice on where I should go/how long to spend in each place (assuming I arrive in Rome).

There are so many places to see that it seems really tough to narrow the options down.
Any suggestions are welcome!

Oh and also if anyone has suggestions on where to START when planning an itinerary that would be great. Seems really overwhelming at first!

Lucky you, Nathalie. You are not at all early in planning this trip. Not late, but you should begin booking your plane and lodgings in the next month or so.
My suggestions:

1. Add to this post:
*Anyone in your party with special needs?
* Your interests. Examples: Art, architecture, churches, ancient ruins, boutiques, large cities/small cities/charming villages, bike tours?
*Do you want to rent a car or stay with trains and buses?
* For hotels, your budget.

2. Look at the Fodors Toolbar for the section called "Destinations" and read up on Italy there. Get a guidebook with lots of photos.

3. Post again with what places really interested you. People will help you arrange your itinerary and how many days for each city/region.

Also, this thread is a must read for Italy:
http://fodors.com/forums/threadselec...p;tid=34443340

NathalieM,
Cosider staying in each place a week. This gives you three destination try to make one of them in the country. Look at other trip reports to get ideas where you want to go. Here are a couple of mine to get you started.
http://www.fodors.com/forums/threads...p;tid=34811101

http://www.fodors.com/forums/threads...p;tid=34494897
If I can be of help feel free to e-mail.

Henry

To NathalieM

I have suggested this list already to several people, I hope it can help you too.

Depending on what you prefer (fashion, entertainment, art, history, summer vacation, food, trend) I have made a note, next to each city, where you can have any of the above.

Supposing you begin visiting Italy from the northern part, here is the listing of cities/towns I prefer:

Milan (fashion, entertainment)
Turin (history, art)
Portofino, Rapallo (summer, trendy)
Lake Como, Lake Maggiore, Lake Garda (summer)
Genoa (history, summer)
Verona (history)
Venice (history, art)
Parma, Modena, Ravenna, Ferrara (history, food)
Bologna (history, food, entertainment)
Florence (history, art, fashion)
Pisa, Lucca, San Gimignano, Arezzo (history, art)
Forte dei Marmi (summer, entertainment, trendy)
Chianti Region (food)
Perugia, Cortona, Gubbio, Siena , Spoleto (history, food, art)
Rome (history, art, food)
Naples, Caserta (history, art, food)
Capri, Ischia, Sorrento coast, Amalfi coast (summer, food, trendy)
Palermo, Syracuse, Agrigento, Trapani (history, art, food)
Costa Smeralda (summer, entertainment)

Obviously the food is excellent anywhere in Italy, and in any city you walk through history. This is a simple guideline, in order to give you an idea what you can find, depending where you go.

For your hotels, I definitely recommend you to visit the following website: http://www.italyvip.com

Buon viaggio

My advice is simple...if you can...spend a week in the north, a week in the south and a week traveling between the two. For me the south includes Rome and Naples and Sicily, The North includes Genoa, the Lakes(Garda, Como, and Maggiore), the Italian Alps, Milan, Verona and Venice. In between is Florence and Pisa. If you make it to all these places, you will have had a wonderful trip and seen some awesome places. My favorites are Venice, Rome, and the Bay of Naples for Capri and Pompeii, Lakes Garda and Como and Verona because I lived there for two years.

Thanks everyone for the suggestions

Luckily the plane ticket is not an issue for me since I am a standby passenger and can technically book a ticket the day of the flight (a true blessing, but of course there is always the uncertainty of the flight being full and not making it on).

As for accomodations, it's probably going to be the low-budget stuff, no fancy hotels. Do I still need to book these in advance? And if so, how far in advance?

To get around, I will be using trains, do not plan on renting a car.

And my interests include art/architecture/history, and of course seeing quaint villages and beautiful hillsides! Shopping is less of a priority.

and nope, no one with special needs.
Thank you again to all who replied to my post! =)