Help needed to plan vacations in Tuscany


New member
My husband and I are planning to celebrate his 70th birthday this October, flying from Rio de Janeiro on the 17th and returning on Nov 3rd.

Although we have been 3 times to Rome, Venice and Florence, he wants to return to these cities, besides visiting the Tuscan cities of Lucca, Pisa, San Gimignano, Montalcino, Montepulciano and Siena, of course.
My husband is against renting a car, he thinks train is the best way, but from what I have read here, some cities are best reached to by car, so I am thinking on going by train from Rome to Venice and to Florence, and then rent a car (I will have to do all the driving!) to do the rest of trip.

I really want to spend more days in Tuscany, which we have never been to, but I don't know how to distribute the days among the above mentioned cities.
Can anyone help me, please?

Thanks in advance!


Well-known member
Driving in Tuscany

Sounds like a dreamy romantic way to celebrate 70 years.

Trains to the major cities is always a plus in my opinion. The relax and comfort just makes travelling so much more memorable.

Some of the places you are looking at would be right on the route, for example Montepulciano could be an excellent stop between Rome and Florence, you could pre-arrange for a taxi to meet you at the station. It's only a 20 min drive between the station and Montepulciano.

Pisa and Lucca are easy trips on the train.

And if your husband really just likes the idea of a romantic trip with - with no worries about "those crazy Italian drivers" you could also look into the possibility of a car and driver for a trip to San Gimignano, Certaldo, Montereggione or Montalcino and Siena or MOntepulciano and Pienza.

Buon Viaggio!


The Tuscan Expert ;-)
Staff member
I agree with Donna - if your husband is dead set against car rental, you can work around it and both enjoy the vacation! While car is often the best way to move around some areas of Tuscany, you can definitely use trains and buses to get around most of the main destinations.
Pisa, Lucca, San Gimignano and Siena will be the easiest to do by train - while Montalcino and Montepulciano the harder to get to without a car. How about a small group tour from Siena to Montalcino or Montepulciano?
It will be less expensive than a private driver/tour and will permit you to visit these last two places without the worry of bus schedules.

I'd suggest using Florence as your base for part of the trip and from there doing day trips to Pisa and Lucca, then moving on to Siena for the rest of the trip and from there doing the day trip to San Gimignano and then to Montalcino and Montepulciano. In particular, take a look at these 3 tours:

These are additional tours from Siena:
while these are many other tours from Florence, including into Chianti:

November will be a great month to visit - less visitors and everything a bit more calm - perfect for a more relaxed vacation celebrating your husband's birthday!