Help with planning trip for Sept 2016

Not a bad itinerary though I'm sure people who are more experienced have more specific feedback. I am wondering why you are flying in and out of Rome? Pisa has an airport as does Milan...... I have used both of those. I think Venice and Florence have them, although I have not used them myself. Think about flying into one airport and out a different one..... it is called flying "open jaw."

Thank you Ray. We have family in Rome so that is why we are flying in and out of there. We have already purchased our fare. :(

Looks like you will be seeing a lot of amazing places! I am sure that each one will give you lots of memories. There is one change in schedule you might want to consider: the train from Cinque Terre stops at both Pisa and Lucca on the way to Florence. And honestly, Pisa would not be on my list especially if sharing the time with Lucca. I only discovered Lucca last year and can't wait to return! I was there in June and found the place and the people interesting, friendly and more than helpful. I assume you are returning the car in Siena. Consider taking the bus to Florence and then the train to Cinque Terre. The bus is far more scenic - and beautiful scenery there is to see. Have a wonderful trip!!!!!

Maybe overnight in Pisa/Lucca ...

Sept 12th Return car rental in Siena, take train to Pisa/Lucca
Sept 13th Cinque Terre
Sept 14th Cinque Terre
Sept 15th Cinque Terre
Sept 16th Florence
Sept 17th Florence
Sept 18th Venice

Thank you Robert and David. To be honest with you, I have not done a lot of research on Lucca. Will look into it more now that it's been suggested. Pisa I hear is really only a couple of hours of seeing the sites from what I understand.

I would stay in Pisa, as the trains are easier to Cinque Terre from there.

Sept 12th Take a morning train to Pisa and dump luggage at your hotel, before continuing on to Lucca.
Trains take approx 30mins from Pisa-Lucca and are quite frequent, usually every 30mins until approx 9:30pm.
Spend the afternoon & evening in Lucca, returning to Pisa after dinner.

Sept 13th Morning to check out the Leaning Tower (Piazza dei Miracoli) before your train to Cinque Terre.
IC 35674 / Dep 13:42 PISA CENTRALE (Italy) / Arr 14:56 MONTEROSSO (Italy)

I would try to stay in Lucca, I have done so twice, because I love it there. Walking/biking around the wall is so relaxing, quiet little town, there is still great architecture to be seen, and the food... the food...

You have a fine itinerary and I would not add a stop in another city, i.e., Lucca. But here is what I would do: keep your car as far as La Spezia on Sept. 12. The train trip from Siena to La Spezia involves three trains, three hours, and a lot of schlepping. We did it once several years ago, having no knowledge of what a pain it woudl be, and what's worse, the trains were so crowded we had to stand up for two of the hours! Keep your car, visit Lucca and Pisa on the drive to the Cinque Terre that day, and on Sept. 17, spend another day in fabulous Firenze!

I almost forgot - Lucca was the home of Giacomo Puccini, the great opera composer. Check to see if there is a Puccini concert the evening you are in Lucca. It's just one more thing that makes the place very special. I went to a few last year (occupational hazard, I'm an opera singer) and was more than delighted with the quality of the performances. Concerts start late and end late so staying overnight in Lucca is a good idea.

You're right, Pisa is a couple of hours at the most. Check train schedules to see what makes the most sense for you. As much as I love the train system in Italy the connections aren't always convenient. Enjoy!

Laurel is spot on. Keep the car to La Spezia. Lot's more options.

I agree leave car in La Spezia, stay overnight in Lucca. Take a day trip to Pisa you really don't need to stay longer.
Have fun
Lorieann

There are lots of musical events in Lucca, a city I return to often for no reason other than I am happy when I'm there. Lots to do in a smallish city. Many concerts are free.