Siena as a base for Heart of Tuscany tour

Hello shom, and welcome to the boards,

Most people here (myself included) will advice you to lay out your itinerary by nights rather than days. This seems like a clearer way of defining where you are staying each night which then helps with hotel reservations and other planning. Also be aware that 1 night somewhere is not even a full day and you need two nights somewhere to get an entire uninterrupted day.

So if your itinerary by nights is:
1 Siena
2 Tuscany somewhere
3 Tuscany somewhere (else?)
5 CT
6 CT
7 Florence
8 Milan?

I would see this as whirlwind busy. The day tour of Tuscany is schedule many people do but here you don't get a full day in Siena and you have one full day in CT. I generally try to never spend 1 night somewhere unless it is for travel logistics like flying out the next day. Don't underestimate the impact of arriving in town with bags, finding the hotel, checking in and then checking out again the next day will have on your "day" someplace versus having a full day in that town without check-out concerns.

Have you considered using Siena as a base for car based Tuscany sightseeing? You could spend 3 days in Siena and easily day trip to San Gimignano and Volterra one day and then maybe south to Pienza and Montalcino the next day. Dropping a rental car off where you rent it will save you a drop-off fees and it will give a real feel for one town spending several nights there rather than 3 different places.

I think one of the best parts of travelling to rural areas is falling into the slower pace of life and getting at least a taste of what that slow pace of life might like... so my impractical advice is take enough time in places to try and experience them not just "see" them. We just stayed in Siena for 3 nights earlier this year - after having only day tripped there before - and there is something so different when you're having a leisurely sprtiz on il Campo at dusk when the horn blaring, drum beating, flag throwing parade from the Oca (goose) contrada shows up to parade the palio flag around the piazza to loudly remind everyone that they last won the famous horserace. But everyone's time/schedule and interests are different so just make sure your plan fits your "must sees" and travel style.

The practical advice I would give you is ditch the car before CT because it is a liability and you don't need it to get to Florence. Whether that is in La Spezia right near CT or in Pisa or someplace on the way that's up to you. Trains work well pretty much everywhere in Northern Italy except for rural Tuscany where a car is pretty much required so use it for that and then drop as soon as logistically feasible. Also be aware of ZTLs (limited traffic zones) in many small towns and city centers and the risks of parking your car with your luggage stored in it. This is one reason people tend to advocate for home bases and trips from there rather than travelling with your bags from town to town by car.

You'll get tons of advice here. Take what sounds right to you and your style and plan then trip you want.

=Tod

Ciao Shom. I agree with what Todd has written. The only change I would make is to go from Siena to Florence then to CT and finally Milan. You can leave the car in Siena, take the bus/train to Florence and from there the train to CT (or La Spezia) and finally Milan. That way you are moving further north at each step rather than circling back to Florence from CT.

Enjoy

https://www.wanderingitaly.com/maps/valdorcia.html

https://tinyurl.com/5eum2na7

https://www.cntraveller.com/article/travel-guide-val-d-orcia

https://tinyurl.com/2rthwxvy

Trip report: https://tinyurl.com/4fsms3wk

You are moving around too much. Leaving Tuscany drive to La Spezia and return the car to Avis. Then visit a CT village and take the train to Milan. For an early morning departure, spend the night at a Malpensa hotel, not needing to arrive until dinner time.