Travelling to Venice Sept. 24, 2 days Venice, train to Florence late on 26th, train to CT on Sunday 29, stay in CT. Train to Siena on 30th- rent a car in Siena for hill towns on Oct. 1st and 2nd. Train to Venice evening of 2nd. Depart Venice Oct. 3 late afternoon. Any suggestions for shifting time frames? Already have hotel for first two nights in Venice.
Not sure what your plans are for CT, but you will not get to see a lot, given one night stay; ditto for Siena. Easy to get to Siena from Florence, but will take you a fair bit of the day to get to Siena from CT. I liked CT very much but if it were me, given the time you have and the desire to see hill towns also, I would just go to Siena and have two nights and a full day there. (or I would go to CT and forget about Siena and hill towns - maybe stay an extra day in Florence and take a day trip to San Gimignano - which would give you a taste of Tuscan countryside. SG can be very touristy - we went, planning to walk in the country around SG during the day with overnight stay so that we could be there during more quiet evening hours. Got rain, which shortened walk, but also reduced tourists, then the sun came out in the evening and it was beautiful. It's actually very pretty even just walking around the outside wall of SG - nice path for doing that. Even just looking out from the walls gives a sense of the countryside. May well be other small places close to Florence that others would recommend - can only speak to where we went.