13 days in Italy - does this itinerary look ok?

Jeff, it looks doable but you may need some wiggle room in case a train is late, you get lost or need more photo ops while driving, that kind of thing. Take a look at booking.com for reviews and descriptions of accommodations in your price range - they have tons of listings.

Thanks Zoe. I am hoping it will be enjoyable. We actually had Orvieto and Civita on the list since Rick's guidebook rated them highly (especially Civita), but in the end decided to cut them out since we felt it would be too hectic (still looks a bit tight - wish we could have a few more days!)

I will look at booking.com - have you had any experience with airbnb? It looks fairly easy to use, and prices look pretty good there too.

the pace is a little fast for my taste, but it is doable. Venice is amazing and I'd spend another day there rather than spend a full day going to the Cinque Terre for only two nights. You would have a VERY early departure to do, as you say:
Cinque Terre: (arrive around noon/1PM on 7th), small hike in the afternoon, visit the 5 towns on 8th, leave 9th morning. For the amount of time and money to be spent going to the CT, you might consider devoting those days/that money to Tuscany so you can see more towns.

Recently returned from 2 1/2 weeks in Italy. The itinerary is doable - but I agree with the other posters, it's pretty fast paced even for a seasoned traveller. Bear in mind that each change of location is going to eat up anywhere from 1/2 to 3/4 day so you need to balance that against what it is you really want to see to make sure you are making the best use of your time - it really is all about trade offs! I guess my biggest piece of advice would be for you to decide what you want to see (as opposed to what Rick suggests) and then plan your days/itinerary from there. Not sure where you are flying in from, but your first day in Venice you may be a bit foggy from jet lag - if it were me, I'd also skip the Cinque Terre and add another day to Venice - I think you are spending more time in transit than you will there and thus, may not be the best use of your time. One thing to bear in mind is that Italy works a little differently than other parts of Europe - sites aren't open all the time and the opening/closing/tour times can make efficient sightseeing a bit challenging at times - hence my advice to figure out what you really want to see and let that drive the itinerary. Since this is your first time to Europe, plan on budgeting in time for getting lost and figuring out how things work!!!
To maximize your time, Siena could be done as a day trip from Florence which would eliminate the need to move hotels.
I'd revise the itinerary to something like this -
Arrive Venice on the 5th -
6th, 7th and 8th - Venice - gives you time to wander the streets, see the Duomo and Doge's Palace and visit one or two of the outlying Islands.
Train to Florence on morning of the 9th
Florence and Sienna - 9th, 10th,11th and 12th (Pisa could also be done from Florence along with a visit to Lucca)
Rome - 13th - 16th
With Rome, bear in mind that you will just skim a bit of the surface - we were in Rome for a week and did not see nearly everything!
Italy is wonderful but is best enjoyed, I think at a more leisurely pace.

I'd suggest skipping the C/T and add it to Venice. Your time is a little short.
Siena is a good day trip from Florence via bus. You'd do better to just stay in Florence another night.
The drive down to Orvieto is very easy by toll road/motorway, and it may be a 2 hr. drive from Florence. But you'd really need to fit in some other hill towns, like San Gimignano and Volterra, to where travel by car would be worth it.
We too love Orvieto, and the train trip into Rome Termini took us about 70 minutes.
If there is anyway possible, another couple of days in Italy would be icing on the cake.

For train travel you need to allow time for getting to the station, waiting for the train, getting from the train to the next place you are staying... It will take more time than you think it will. I agree that the long travel to get to the Cinque Terre versus the time you will have there isn't really worth it. I would add that time to Tuscany, so you can see the desired Hill Towns.

Nancy's suggestion looks good. If you want the flavor of a smaller village, stop in Orvieto for 1 night. It's a quick train ride from Florence and 70 minutes to Rome. Last trip we arrived in Orvieto around Noon, dropped the luggage off at the hotel, and wandered and explored the rest of the day, had a late dinner, then took the an 9:00 train to Rome the next morning and still had a full day the first day in Rome.

Goodness, thanks for all the replies Laurel, Nancy, David, Andrea, and Karen! (and sorry for late replies on my part - I'm in Tokyo, so I'm likely asleep when many of you are posting :)

I would REALLY love to spend more time in Italy, but we're actually visiting Prague first for 4 days before heading on to Venice, so it would be tough to take off more time off from work than we already have scheduled (in total, almost 3 full weeks). I suppose one option would be to see if we can cut down on time in Prague from 4 days to 2 days... for those of you who have visited both Prague and Italy, would you recommend this? (not even sure if it's doable, I will need to contact the airline to check)

I agree, the time taken to reach CT seems a bit wasteful (6+ hours in the train). However, I keep hearing (and seeing) so many beautiful photos of the CT area that I'd like to try and shoot it too. (I'm a bit of a hobbyist photographer when I find the time; for an idea of the type of stuff I shoot you can check out my posts on G+:: https://plus.google.com/u/0/+JeffMatsuya )

The plan for an overnight in Siena came about because my SO read that Siena was one of those places best enjoyed after the day-tripper crowds have left for the day. Hence her wanting to spend a night there.

I will discuss with her this evening, and consider cutting out CT to make more time for Tuscany. Perhaps the Tuscan countryside can make up for missing out on the hill/oceanside views...

If Prague is your first stop, I would not change the number of nights there. Keep the overnight in Siena, your SO is right about the magic of it at night.

Plan to return.

Thanks Zoe, she will be glad to hear that about Siena :)

As for me though - after reading everyone's replies, I got on the phone with the airline after my last post and have modified the flight schedule a little. Now, we leave Tokyo 1 day earlier, and spend 3 days in Prague instead of 4, so that gives us an additional 2 days for Italy! I will update my original post to reflect these dates, and see how to put those 2 extra days to best use :)