Rome to Sicily in two weeks

If I am flying into Milan, do you think I will have time for Venice also? or is this too much for one trip? Milan -Venice -Tuscany -Almafi Coast - Sicily.

It would be helpful for you to post a little more information. Is this your first time to Italy? When will you be there? Why the interest in Sicily? What do you enjoy doing? etc.

Yes, my fiance and I will be traveling to Italy for our honeymoon Oct 16-30th. We have to end our trip in Sicily, my fiance's relative's live there and we are due for a visit. We have dropped Venice from the itinerary and have decided on the following: Fly to Milan, train to Cinque Terre (one day), train to Florence (one day) and then driving day trips to Chianti, Siena and Montepulciano (two days). Montepulciano to Rome via train. Rome (two days)and then off to the Almafi Coast and Capri (three days). Naples to Sicily via ferry. Sicily (four days). Is all of this possible?

....also; what type of transportion have you factored into your plans? Traveling from one part of Italy to another can eat up a lot of time.

If this is your 1st trip, you may want to leave Sicily for another trip. The seasons also can have a big impact on your trip. Sicily can be unbearably hot in the Summer, but amazingly beautiful in the spring.

I'm surprised that no one has yet said that you are trying to cram in too many destinations, so I'll repeat what has often been said here. Every change of location eats up a significant chunk of a day. Single night stopovers are a waste of your time. You don't mention your interests; but if art and architecture are among them, then just a day in Florence is inadequate. One day is sufficient for Montepulciano, unless you are meaning to use it as a base for visiting the other parts of Tuscany (?). If you are visiting the Amalfi Coast, you can omit the Cinque Terre. The former is more beautiful and much more interesting. Is your return flight going to be from Rome? If so, be aware that getting from Sicily to Rome is time consuming unless you fly.

OK, let me revamp my itinerary. Knowing that I have to spend 5 days in Sicily and I have 14 days in total to travel. What other places would you recommend we travel to? Only towns south of Rome? Thank you for your help.

Your original idea actually works, with a few modifications. Spend the first 3 nights in Rome. Then rent a car and head to Siena, stopping to enjoy Montepulciano on the way. Stay in or near Siena for 4 nights, exploring Tuscany with the car for the next 2 days and then returning it. Devote the 4th day to Florence (easy bus trip from Siena). Then head by train to Sorrento for 2 nights. You'll actually get a 3rd day in Sorrento if you take an overnight ferry from Naples to Sicily, or spend that 3rd day exploring Pompeii or Naples. Fly from Palermo or Catania back to Rome for your flight home. You can play with variations of this, such avoiding Florence on Monday when the major museums are closed. Also, you could do Tuscany first by renting a car at the Rome airport and save the 3 nights in Rome for the end of your trip. Keep tinkering with the options and it will all come together.

Haven't a clue where you are flying back to the US, however, I found a super fare on AirBerlin.com from Palermo back to Rome for my trip in March

Thank you to everyone's responses! Frank, I think we are going with your suggestions! Thank you!