14 Nights in Italy

Start with a guidebook.

JKC is right; your question is much too broad to answer without writing a book. Fortunately, the host of this website has done an excellent one, and Rick Steves Italy should be your first purchase. Then, look at some other guidebooks to get other opinions. But for a first trip to the places you listed, Rick has you covered.

This forum is much better suited to focused questions, and to things you can't easily find in a book. For instance, "what should I see in Rome?" is too hard to answer. But "I'm very interested in seeing an opera in Rome while I'm there - does anyone have any tips?" is going to get useful responses.

I can say that in 14 days you can't go to 6 places and still enjoy your trip, so you will have to cut down your list. That's particularly true if you have to return to Rome to fly home. If you bought an open jaw ticket, into Rome and out of Venice, it makes things a bit easier (no time lost backtracking).

When is your trip? If it's not too soon, you can save a lot of money on advance train tickets. If it is soon, you will want to nail down hotels and make reservations for some things NOW (like the Uffizi and the Accademia in Florence and the Borghese Gallery in Rome). Again, Rick's book has details on all of this, as well as lots of things you didn't even know you needed to know.

Sounds like to much to me. I'd cut out Amalfi, Pisa and the Ct and include Tuscany. Where do you fly out of?

I'm going to follow this guide through Italy.
http://thetrustedtraveller.com/italy-train-two-week-itinerary/
It mentions some of your places, and has notes to add other places that you have mentioned down the bottom. If you follow this guide and leave out Milan, but add Pisa as a day tour and Amalfi coast you should enjoy it. Florence and Pisa are in Tuscany.

wow...Thank you so much for all the wonderful advice. After some thoughts this is what we decided. It is a packed itinarary but we're thinking this way we get to see little of everything then maybe go back to the places we like a lot in the future. :)

Day 1 - Land in Rome at 10:00am (Base for Rome)
Day 2 - Rome
Day 3 - Rome
Day 4 - Rome
Day 5 - Head to Pompeii early morning then check into the hotel in Sorrento (Base for Amalfi Coast) in the evening
Day 6 - Capri
Day 7 - Amalfi
Day 8 - Amalfi then head to Florence in the evening (Base for Tuscany)
Day 9 - Pisa
Day 10 - Cinque Terre
Day 11 - Florence
Day 12 - Florence
Day 13 - Florence
Day 14 - Head to Venice Early Morning (Base for Venice)
Day 15 - Venice
Day 16 - Fly home from Venice

Any suggestions on the must do's or don't with the above itinarary? We have hotels booked already but no trains or guides.

I'd take a day off Florence and put it toward Venice. Also, realize Pisa does not take a day to see. It's a day trip from Florence. It works very well combined with Lucca. If you see Lucca in the morning and Pisa in the afternoon, you miss the worst of the tour bus crowds, and the marble in the Field of Miracles looks lovely in the afternoon light. I did this day trip in March 1989, but it remains one of my best travel days ever.

Have you looked at the travel times between these places? Use Trenitalia to see schedules: http://www.trenitalia.com/tcom-en. Even the English version works better if you use the Italian names for stations:

Rome = Roma Termini
Naples = Napoli Centrale
Florence = Firenze SMN
Venice = Venezia SL

Again, it's all in Rick's Italy book.

I assume nights 5-7 are all in Sorrento and that you are only daytripping to Capri and Amalfi which would be good. If you are actually switching hotels, you will be wasting a lot of time moving luggage as opposed to visiting.

I also assume nights 8-13 are all in Florence and you are day tripping to Pisa and CT. If not, see above. In any event, CT is a long way to go from Florence for a day trip. I think it will be a long and unpleasant day. You will already have the Amalfi coast experience. You should consider cutting CT and just add a night to Venice as suggested.

PS. You should post in the Italy forum. Lots of italy experts post there.

Check on your flight time out of Venice... maybe reverse the trip as those flights are often very early. Venice is a good place to start any trip.

Edit... ok looks like maybe you already have flights?
For my early flights out of Venice I have stayed closer to the airport. Have a last nice dinner in Venice, make your way to the airport hotel, and have a shorter route to the airport if you have a super early flight.

Why not overnight in Pisa, to make it easier to get to CT next day
Day 8 - Amalfi to Pisa via Naples, Rome, Florence
Day 9 - Day excursion to Cinque Terre
Day 10 am - Pisa
Day 10 pm - Florence