Melissa5

Shelbyd, what's your maximum budget for hotels? I left an answer under your other post as well.

maitaitom

Here's my six cents worth.

Fly to Milan - train to Cinque Terre area
3 Nights CT (I like to start trips in a relaxing spot to unwind)

Morning train to Florence
3 Nights Florence

Morning train Venice
3 Nights Venice

Morning train back to Florence gets you in by noon
Rent a car - take the 222 scenic route through Chianti area to Siena
3 Nights Siena
Explore
Take a day to explore San Gimignano and Volterra
The the other day to see Pienza, Montalcino and perhaps Montepulciano or one of the Abbeys in the area

Drive to Rome - drop car
4 Nights Rome

Fly home

I know that's 16 days, so maybe take only two nights in CT.

Have fun.

italylover

Hi Shelbyd,

I spent two weeks in Italy last July, and not only was it one of the most amazing experiences of my life, two weeks was definitely not too long of a time to spend in Italy.
I will tell you what our itinerary was, and maybe that will help you with your planning....(side note, I went with two close friends, and we are all in mid-20's)
We arrived in Rome and spent 6 days there, now I know you said you don't want to spend more than 3 days in a city, but Rome really deserves more...we spent 6 days in Rome and it still wasn't enough to see everything...however, we did take a day trip on one of the days in Rome to a great town in Tuscany called Montepulciano, where we bought some of what is considered one of the best wines in the region, as well as fresh olive oil. What was nice about visiting this town while staying in Rome was that Rome is a very fast-paced, busy and crowded city, while Montepulciano was peaceful, relaxing and very green! Beautiful hills and vineyards everywhere, and cobblestone streets added to the charm! We just took a train from Rome to Montepulciano and back in one day, your hotel would be able to help you with logistics. This way, you knock out Rome and Tuscany at once, and get to spend a little more time in Rome, if you extend your stay to say, maybe 5 days.
Next, we took a train to Venice. Beautiful!!! We stayed 2 days in Venice, and felt it was more than enough. You can sightsee, shop, take a gondola ride, eat by the water, and relax in those 2 days, and not feel rushed at all. Consider taking a day away from Venice and add to Rome!
Next, we took a train to Rimini, a beach town that we heard was a real party place for younger people. Boy, were we misinformed! We stayed in Rimini for 2 days, and though we enjoyed laying out at the beach and relaxing after all the walking we did in Rome and Venice, the water was not that great (we didn't even swim in it) and the nightlife was not that great either. I'd recommend visiting a different beach town, maybe on the Amalfi Coast?
Finally, we took a train to Milan and spent 3 days here. I would recommend flying into Rome and departing from Milan, since the two major airports are in these cities. I noticed Milan wasn't one of the cities you mentioned, but I would definitey recommend going here. You can see The Last Supper (make prior reservations), which was amazing. There's also the Duomo church which you can climb to the top of! Also, we had dinner at JustCavalli, which is a restaurant owned by famous designer Roberto Cavalli, it was decorated like nothing I've seen before, with beds outside, live music, a great atmosphere...but very expensive and most of the diners are models. Still, we had a great time there. While in Milan, we took a bus to Switzerland, which is only about an hour away from what I remember. We went to a well-known outlet mall there, FoxTown, and got great chocolate. There is a Gucci outlet in this mall also if you're interested. On the way there and back, you'll get to see Lake Como, which is beautiful. There's also a casino in the mall as well.
Well, I hope my mini trip report will help you in deciding what you will do. Please post again and let us know what you decide, and have a great time in Italy!

RufusTFirefly

Two days in Venice are more than enough if you don't want to see any of the sights. By that standard, two days are more than enough in Rome, London, Paris, New York, Florence, etc.

gfeibleman

In 2001 we did a first timer trip with experienced friends (by car). flew into Milan for 2 nights, lake Garda then off to venice for 3 nights, then 1 night in Vincenza, then down to Spoleto (Umbria) for 2 nights, off to Rome for 4 nights, up to Orvieto then to Castillano in Chianti, (Tuscany), then Santa marguerite for 2 nights on the Italian Riviera and then up to Lake Orta for 2 nights and back to Milan in the morning to catch our plane

I think most places we stayed 2 nights.

A great introduction to Italy. I think it was about 3 weeks.