Itinerary help-- too ambitious?

What is it you are wanting to see/do on this trip? See the big sights? Just hang out and soak up the culture? Personally I would drop the CT (very similar to Amalfi), add another night to Venice. What all do you want to see in Rome? Maybe drop a Milan night and add to Rome.

A day trip from Florence to Cinque Terre is some five hours on the train. Better spend it otherwise. A day trip to Siena (1 hr on a direct bus) would be a much better investment of your limited days.
The same is with »doing« Venice from Milan. That a lot of train and little of Venice. Go from Florence to Venice and spend at least two full days there before moving on to Milan.
For the longer train trips advance bookings on www.trenitalia.com/tcom-en gives you considerable discount.

We wanted to see the sights of Rome (the Vatican, Colosseum, etc.), but otherwise just soak in the culture in all the other cities. We wanted to hike the CT so I don't think I will be cutting it out of our itinerary.

I was thinking we could just spend a day traveling from Rome to CT (stopping over in Florence for a gelato) and then spend a night there and then adding another night to either Venice or Rome. Thoughts?

Is there a reason you're spending 4 nights in Milan?
If not, spread those 3 nites around. Leaving the last nite in Milan.

Your flight milan(MXP) to Naples (NAP) may be too close. The 8:35 arrival time is when the plane lands. You then have to get to the gate get off the plane and go thru passport control. Then find the gate for your departure. Might be hard to do in 1 hour 25 minutes.
Are these flights booked as one ticket on the same airline or partner? If not, you may in this short time, also have to pick up your luggage and check in again.

Lots of questions, but we can be of more help if we know the answers.

Look at http://www.rome2rio.com

For transportation between cities.

For train tickets see
http://www.trenitalia.com/cms/v/index.jsp?vgnextoid=ee13721bdd69a110VgnVCM1000003f16f90aRCRD

Definitely looks like too much Milan and too little everywhere else.

As the poster mentions above unless your pit stop in Milan is part of the same ticket, you don't have enough time to get your luggage and recheck in. I would think you need 3 hours minimum in between flights to do this if flying on separate tickets.
if all the same ticket, no worries the time is sufficient.

your idea of starting in the south makes sense to me, that is what we have done.
I would drop CT entirely ( we have been to both) and less Milan. if you could drop CT you could get your share of beautiful coastal scenery at Sorrento, capri, positano, pompei. there is so much to see on the amalfi. also, do you particularly want to see naples? could you save time going straight to amalfi from the airport.
there is also a fast train from milan to naples , if flights don't fit?

A day trip to CT really wouldn't do it justice. For CT I would advise at least two nights. The evenings, after all the day trippers/tour groups have left, is a completely different place.

If it were me, if you are roundtripping from Milan, I would do something like this.

Day 1-- Arrive in Milan, Catch train to Venice (overnight Venice)
Day 2-- Venice
Day 3-- Morning train to Florence (Stop in Padua on the way?)
Day 4-- Florence
Day 5-- Florence (Day trip to Pisa?)
Day 6-- Florence
Day 7-- Morning train to Naples. Circumvesuviana to Sorrento
Day 8-- Sorrento/Pompeii
Day 9-- Morning in Amalfi. Evening train to Rome
Day 10-- Rome
Day 11-- Rome
Day 12-- Morning train to Milan.
Day 13-- Depart from Milan in the afternoon.

Joe

Your flight arrives in Naples before midday - plenty of time to get a transfer directly to Sorrento.

Day 1-- Arrive in Milan. Fly straight to Naples. Head directly to Sorrento - 3 nights
Day 2-- Day trip to Capri
Day 3-- Day trip to Pompeii (& Naples ??)
Day 4-- Train to Rome - 3 nights
Day 5-- Rome sights
Day 6-- Rome sights
Day 7-- Train to Florence - 3 nights
Day 8-- Florence sights
Day 9-- Day trip to Cinque Terre (or Siena ??)
Day 10-- Train to Venice - 2 nights
Day 11-- Venice sights
Day 12-- Train to Milan - 1 night
Day 13-- Depart from Milan in the afternoon.

David and I tend to agree/disagree...

Day 7. Rome-CT. 3 1/2 hrs.

Day 8. CT

Day 9. CT-Florence spend nite.
2H08m.

Day 10. Florence-Venice 2H05m. Early afternoon train.

Day 11. Venice.

Day 12. Venice- Milan. 2H35m

Day 13. Travel.
Milan central. Malapensa express. 1 hour. Allow 2 1/2-3 hours to check in.

Edit. Take the Curreri Viaggi bus from NAP- Sorrento 1H20m

I am very excited Gerri is on 999 posts !!

Even if your flight to Naples is on the same ticket, I worry if it is doable. 10.00 is the scheduled time the plane pulls out of the gate. The gate usually closes at least 20 minutes before that. Even if the plane is stuck at on the tarmac, once the gate's closed, you can't board. That gives you just over an hour to get off the plane, go through passport control and get to your departure gate - maybe with a security check to boot. That's really really tight even if the plane lands on time and isn't delayed on the tarmac and the doors open right away and you're at the front of the plane for a quick exit. I assume you are traveling with ONLY carry-on luggage which meets the requirements for the Milan-Naples segment.

Venice is too far from Milan for a decent day trip. It's 2.5 hours by train each way. Add about .45 hour to/from your hotel in Milan to the station and a few minutes to find the train (assuming you bought the tickets in advance so you don't miss the train because you're waiting in line at the ticket counter), that's 6.5 hours just to/from the Venice train station. You'll be in Venice the same hours as all the day-trippers from the cruise ships and it takes a long time to get anywhere. It's an hour on the vaporetto to St Mark's Square (Basilica, Doge's Palace), it's at least 1/2 hour walking if you don't get lost and don't stop for anything and it's not crowded - but you will get lost, you will dawdle and you won't be able to walk fast because of the crowds. If Venice is important, spend 2 nights there between Florence and Milan.

Florence to the CT isn't much better. It's at least 2.5 hours on the train, though easier to get to/from the train stations at both ends. Again, you'll be there at the same time as all the cruising day-trippers. If the CT is important, spend 1-2 nights there between Rome/Florence or Florence/Milan

I might be in the minority, but just getting back from our trip so its is fresh in my mind. We hit all the major sites in Rome in a day, but 2 would have been nice for sure so I support that. Florence is beautiful, could spend a couple days there. I wouldn't miss the CT, it was one of my favorite spots for sure! Milan was not for me, very much not what I liked about Italy. They had the best cathedral in my opinion, and I was glad to see the Last Supper but otherwise it was nothing special so I would pair down those days. Venice is worth a couple days or more. I could have easily spent a week there.

My trip was:

Day 1 arrive in Milan, drive to Montecatini Terme (hotel for 5 nights)
Day 2 train to Rome (roundtrip) 10 hours actually in Rome
Day 3 drove to La Spezia, parked car took train to CT visited all 5 towns
Day 4 trains on strike, drove to Florence
Day 5 drove to Sienna, San Giamagnio, and Volterra
Day 6 drove to Venice, parked
Day 9 drove to Milan, saw the Duomo and Last Supper
Day 10 flew home to states :(

Your itinerary is not too ambitious, you CAN do it all. Train travel is easy. I do agree that you have too much time in Milan. Spend the night in Venice (or nearby Verona) instead of making it a day trip. And I think CT is worth the trip, and spend the night. Have a great time. I recommend gelato every single day you are in Italy.

I was in Milan last week. The airport is very large and I have some doubts you will catch your connecting flights considering you also have to do Immigrations. I also had a very ambitious schedule but dropped it. There is so much to see and just running /driving flying around to see all is just not manageable. I think you would need a vacation afterwards. Rome alone has so many things to offer! Cinque Terre from what I understand I worth more then a day trip. Plus you really need to start booking places to stay asap. I just pre booked all my B&B's for my end of August trip.

I stand by Davids take on getting to Amalfi area ASAP. 12 nights goes by fast.
here is my twist

2 Nights somewhere on Amalfi coast (google some of the towns you can choose from and keep itinerary simple. Just the location is a sight within itself)
---train
4 Nights Rome (SOOO much to see and deserves relaxing strolls on its sreets that are more beautiful than you may expect)
----train
1 Night Orvieto (same tuscan taste as Florence but quainter and 1 hr tain from Rome towards Florence- very accessible w. train which is rare for hill towns--gorgeous; you will NOT regret it)
---train
2Nights Florence (compact. Narrow down must sees and enjoy cheap good food and art)
---train
2Nights Venice - amazing but I wouldnt stay near touristy sights. Make sure u stay IN venice.
----train
1N Milan fly home . You will not regret it

Choose CT or Amalfi Coast. If you choose Cinque terre your trip will feel significantly more relaxing from the get go.. no need for another flight or bus from naples to x y or z. I would do as follows for best flow.

Train to La Spezia from Milan then into CT
--Stay in Vernazza or Manarola. And eat at IL Pirate in Vernazza... plan to visit each town since they ar 10-15 min away from eachother by train... boat.. ect. Great hikes.

---3.5 hr train from Milan
2N Cinque Terre
---3 hr train
2N Florence
---2 hr train
1N Orvieto
---1hr train
4N Rome
----Take speed train 3 hrs 45 min
2N Venice
---2.5 hr train to Milan
1N Milan.. fly home

Either of these itineries I have mentioned has a lil bit of everything. ! Take grocery finds and snacks with you on trains and enjoy the views.
I feel very confident of this Itinerary since we did something similiar in September. Book trenitalia ASAP. Review check in and check out times for hotels or apartments to help you choose train travel.

Lastly... just choose already so you can book apartments.. it is a high time to go and the longer you wait the less options there wll be and for a higher cost ecspecially for Amalfi and CT which will be full of Italians who tend to have their vacation time in Aug. AirBnB is the best IMHO. STAY CENTRAL everywhere u go. Its crucial for this pace of travel. You can be ambitious but you have to do it wisely--itinerary that back tracks least possible.. give longer time where needed-- book in advance, etc. End rant.