Newlywed trip to Italy- no idea how to plan
 

My husband and I are traveling to Italy in July. The first leg of our trip is in Milan for school and then we have 7 days on our own. My husband has been to Italy, but I have not- and we're both pretty unfamiliar with planning on our own. Any ideas for itineraries and cheap places to stay?

What are your interests? Will you be renting a car or taking the train? Where are you flying out of?

Also, the title implies that this is your honeymoon, but you say that you'll be in school in Milan. If it's your honeymoon, you might want to treat yourself to a couple of nights in a nice hotel.

I do in this order:

Attractions --> places to stay --> transportations --> Attractions and so on until I reach a good itinerary.

I use guide books to get a list of attractions and put them in groups: want to visit, may be, and definitely not. Most guidebooks are quite overwhelming: one attraction after another without giving senses of which are worth going. I usually START with Rick Steves for a new city: he ranks the attractions in the order HE recommends. Obviously he includes items of little interest to you and misses others, but if you do not have any idea, this is a good place to start.

Then I decide if I want to stay all the time in one place, take day trips to nearby places, or move to a next city depending on amount of attractions of interest in that area and transport connections. This is when I decide what kind of transport to take. My in-laws do this the other way: always rent cars and decide where they can go with a car.

From Milan, obvious day trip ideas are Lake Como and Maggiore. Each may merit staying more than a day on its own.

No, It's not our honeymoon. It's actually very near our first anniversary! We have considered renting a car, but we we were not sure if it was needed. I think we'd like a little more of the "off the beaten path" approach. We would like to visit Venice, Florance and maybe Tuscany or Assisi? We are planning to go to Lake Como and Cinque Terre during our off time in Milan and then do a 7-8 day trip after we leave. We are flying out of Milan.

Well, Venice, Florence, Tuscany & Assisi certainly aren't off the beaten path! They're right ON the path. That said, they are good choices. However, with only 7 days (is that 6 nights?), you can only do so much. With 6 nights, I would do 3 in Venice and 3 in Florence with a daytrip from Florence by bus to Siena or another hilltown. But, if you're flying out of Milan, you should probably be back there for the last night, which would only leave 2 nights in Florence, not really enough time for a daytrip. How many nights (not days) do you actually have after you leave Milan?