I think you latest itinerary is excellent, just as it is.

WeisserTee, Thanks for the extra info on high end shopping for the OP. It will probably be useful for his wife. A nice bag or something like that would not be much, but if they buy a lot, they will still have to lug it with them, along with the toddler.

Victorho, don't cut any more time from Venice. Two days is very little there and you can manage that with your toddler. If you don't have one, pick up one of those harness and leash for children. Sometimes they have little backpacks attached, so the child doesn't mind it. That way, you can feel a bit safer near the canals and in a crowd. Use one day to take a vaporetto to Burano and Torcello. Burano is Intersting, lovely for walking and you child will probably like the boats.

Oh good that you mention the leash. There are places where a kid could fall right into a canal. Mine almost did following a balloon.

Yep, use the leash--but let him chase the pigeons to heart's content in St Mark's Square in Venice.

I stayed overnight in Lucca, because I was there a couple of days, but would just do it as a day trip if I were in Florence. Train time is an hour and a half or less from Florence. Many people combine it with a stop in Pisa. That might be a bit tiring with a little one, but you could judge.>

It is easier if you can time your trains to hop one from Pisa Centrale to the next station to the north (forget name always) - a small unstaffed station - no lockers - but a very short walk from the Leaning Tower - have hourly trains then to Lucca. Pisa's main station is way across town from the Leaning Tower area.

Thanks for the inputs.. Evaluating all options..

Need some advise on below,

Trains services - for the inter cities train, I will be booking it in my home country. For those short regional train I will buy it at the Italy city itself. Is that the way to go?

Shopping - my Wife will be excited to look at brand like Prada, Hermes, Bottega, Gucci, clothes/ shoes will be armani, Zara, Ferragamo. Where to shop for items like this, was told the factory outlet for off season can get good discount.

Regional trains in Italy, use a Trenitalia machine. You can buy them all at once if desired. Tickets are undated and need to be validated before boarding, using one of the little stamping machines.

I think there is a time frame in which to use regional train tickets so if so do not buy too early from machines.

A regional train ticket, if purchased at an Italian train station (as opposed to purchased online), is good for <b>2 months</b> from the date of purchase. (If purchased online, I heard that the validation period would be quite short.)

After you have decided to use it and waited in a platform and inserted it into a validation machine to print a timestamp on the ticket, then the ticket is good for <b>6 hours</b> from the timestamp. There are further clarifications such as if your journey lasts more than 6 hours etc (yes, they will let you finish the journey).

I have not purchased tickets from a machine, I have always purchased tickets from a human at a station. Also, I purchased all my regional train tickets at once at a station when it was not busy and no queues.

Reading - thanks for clarification - I knew there was some reason NOT to buy online - besides saving no money and getting no seat reservation since they are not available even on regional trains.

Q - I assume you can break your journey at will with a validated regional train ticket - the reason for the 6-hour window -and can you like go round trip - say Lucca to Pisa and back on one ticket as long as it is in the 6-hour time frame?

You may not know the answer I realize but if do it may be useful to folks doing such trips.

>> can you like go round trip? <<

No, each ticket has a starting point and ending point printed, for example, Lucca to Pisa, or Pisa to Lucca.

If you ask for a round trip Lucca <--> Pisa from a human, you would receive two tickets. One for the outbound Lucca --> Pisa, and the other for the inbound Pisa --> Lucaa.

Thanks again Reading- that's kind of what I thought.