I'm not sure I follow your itinerary - you seem to have missed the time in some places.

I would lay out the itinerary day by day - where you will start the day and if you will travel to another place and where you will sleep.

Also not sure why you are flying out of Milan when you could save a day by flying out of Venice - where you will already be.

I suggest three nights in Venice. It's the worlds most beautiful and romantic city. In my opinion you need two full days to see it. See my report of our latest visit at -
http://www.rimerson.com/

I don't know how you can miss Florence.

Rob

Thanks for your feedback. We are planning on flying to the UK after our stop in Venice, but I thought it would be a good idea to fly from Milan to see the city. However, I will look into flying out of Venice. I'm open to seeing Florence as well, but just very confused on how to plan my time out in Tuscany and now Florence. Thanks again!

Second the suggestion to fly out of Venice. I'd drop Milan, the CT unless you like to hike), and add more time in Florence and travelling to Venice by stopping at some of the smaller cities in route. Three nites in Venice is preferable to two.

Comparing Venice to Rome, I think 2 nights and three days in Venice is perfect. We did 4 and it was almost too much. Have fun!

<< We've decided to skip Florence and spend our time in Tuscany >>

Florence is in Tuscany.

I do not believe that San Gimignano has a train station so you would take a train to Florence and then change to a bus.

3 days is too much for either Siena or San Gimignano unless you have a car and can explore the area.

I don't think there is any one key area of Tuscany. It depends on what towns you want to visit.

I also not not understand your itinerary. You're spending 1 night in Cinque Terre and then taking a train from Florence to Venice? How are you getting to Florence? Why not take a train from La Spezia which goes to Venice via Florence?

Fly into Rome
Rome (3 nights) 2 nights more than enough, two 4 hours half day trips to Vatican and historical sites (book guided tour for both' viator.com) spend evening at Spanish steps and Trevi fountain, and enjoy the historic walks with great food.
Train to Tuscany, stay in Florence, close to dome, plenty to see and walk around, (day trip to Siena and San Gimignano, guided tour, worth every penny with Pisa and wine farm house lunch included.)
Clinque Terre, delete from your itinerary, should be part of 2nd trip. See the best.
Train to Venice from Florence? That's the way to go to Venice. Again great place for 2 nights.
Venice (2 nights) take a 3 hour guided trip,to 3 islands, it's different,
Train to Milan, that's fine too, if time spend 2 nights in lake come specifically in bellagio or lake Garda and a guided tour to Verona from Garda or you can book day trips From Milan, como departs everyday and lake Garda and Verona every Friday only. Hopefully it works out for you.
Fly out of Milan

I would delete CT and Milan from this itinerary. You haven't included enough time to appreciate either. It is not exactly clear how many nights you have but you might consider 3 nights in Rome and 4 in Tuscany. If you have a car stay in the Tuscan countryside and take day trips to Pisa, Siena, San Gimignano and Florence (bus). If you don't want to rent a car, stay in Florence and take day trips to the countryside by bus. Then train to Venice from Florence, stay 3 nights and fly out of Venice.

I would recommend that you rent a car for Tuscany. There is so much to see - both small towns and vineyards. My wife and I stayed in a villa near San Gimignano and took day trips to Pisa, Florence, Lucca, Siena, and San Gimignano.

Gatorman, where near San Gimi did you stay? Would your recommend it?

Caligirl, we rented two villas from private parties - about 10 km west of San Gimi. My sister was working for the State Department at the time and found out about them through work. It was a family reunion, so we had a lot of people.

I don't have the contact info for the villas, but I could try to get it if you're interested.

Personally, and honestly, this is just an opinion, this itinerary, and some of the suggestions for amending it, are insane. Really. Certifiable. This is not any kind of holiday an ordinary human could possibly enjoy.

Here's why:
1. Too many changes, too many places, or both. Every hop you make wastes a 1/2 day, more if it's a big hop, and all yours are what I would call big hops. Or a rough count you are wasting around 1/4 of the waking hours of your expensive trip travelling. What a waste.
2. you are spending such a short time in each place you'll get nothing for the feel of the place you're visiting. Rome? One of the most amazing cities in the world, and you plan on spending just 2 days there. Venice: equally amazing, and you'll be there one day. And what on earth is the point in travelling all the way to CT for one night? It'll take you all day to get there, you get to your hotel, shower, have dinner, go to sleep, wake up and leave again! Madness. Tuscany (where I live): 2 days? People have stayed with us for 3 weeks and still not seen it all.

This trip will leave you exhausted and wondering why people make such a fuss about Italy. If all you see is the inside of a train and your hotel rooms, that's hardly surprising.

Where's the time for a long lunch with an amazing bottle of wine in a hill-top town with stunning views? That is something you might remember for the rest of your life, isn't it?

My advice: at least 4 nights in Rome, and 4 nights in Venice - that's just three whole days in each. Or 4 in Rome, 5 in Tuscany, and leave the rest for next time. Forget any leg less than 3 nights, that is for certain.

With this trip you're unlikely to want to ever come back to Italy as I can't see you enjoying it. You'll be exhausted and everything will be a blur. Photos with no feeling. It's not what Italy is about.

As I say, just my opinion as an Italian and a fellow traveller.

Here here!
Well said.