Rome to Venice via Tuscany HELP


New member
Hi everyone
I am going to be spending some days travelling through Italy with my gf and had the following in mind and would love your take or suggestions on places to stay or see along the way...thank you

Arriving in Rome June 14th and spending 4.5 days there before heading up north from there via car...
Renting a Car and Drive to Florence Starting June 19th early...
June 19th: going from Rome > Montepulciano > Pienza > Montalcino > Siena Or San Gimignano for over night stay ... I need help to find out if all these is too many stops for one day?! should I make a stop in between over night? which of the towns to spend more time seeing
June 20th: Drive from Siena or San Gimignano to Florence Via Chanti and enjoy sights and stop by any place recommended...Wineries
June 20th: return my car in Florence and stay in Florence (sightsee if time)
June 21st: Florence sightsee and take train to Pisa (or tour) for half a day and back to stay in Florence
June 22nd: See Florence and stay in Florence
June 23rd: Train to Venice for 2 days stay there...

Any insight as to whether the shell of our trip is ok or what sights or cities to see / spend time in would be appreciate it.

Thank you,


Well-known member
Place to stay


My suggestion would be to take one day off of Rome and add one day to your tour of Tuscany before reaching Florence. Your itin is perfect but for the time allocated it will be a bit stressing and I believe you would enjoy it a bit more if you had the time to really relax into the scenery.

On your first day out, I would suggest staying near Montalcino, that should give you plenty of time to explore Montepulciano and Pienza. Montalcino is a lovely town and if you can find a place in the city center you will have the evening to walk around and enjoy the cobbled stone streets and rich atmosphere. You can look into doing a winery in the area:

Altesino between Montalcino and Buonconvento - historic cantina, beatutiful views. I have been here and they have a nice tour of the cantina

Siena is really worth the time - it is larger than Montalcino and a bit busier! but it is totally unique and well worth a visit to the main square and the Duomo. Then maybe you can ride into Chianti and head over to San Gimignano for the night - I found a great little winery Fattoria Pietrafitta which had a small stop where you could picnic and enjoy wine & scenery.

Enjoy your travels!


New member
Hi Again
after much consideration we have decided to shave off one day from Rome and add it to Tuscany so dates look lik we will leave Rome on the 18th and head up through Tuscany untill 23rd when we will take a train from which ever city we are staying at on 22nd night (23rd day) to Venice... Now comes sthe big question with 5 nights and if we can rent a car what are the best places to hit and where should we spend our nights?
Do you think 5 nights is enought o get up all the way to Genoa and still see lots? i.e. Montepulciano, Montalcino, San Gimignano, Siena, Florence, Pissa, Cique Terra, ..? which ones to see and where to stay ?
I was thinking of
1st night at Monepulciano or Montalcino
2nd night at San Gimignano
3rd night Florence
4th night Cique Terra
5th night Genoa

However I feel this maybe very crammed and more driving than sightseeing!!! Should we cut out Cinque Terra and Genoa and just spend 2 nights in Florence and an extra night sowhere along the way?
your help is really needed and appreciate it...
Thank you,


The Tuscan Expert ;-)
Staff member
Realistically, you are cramming too much - while distances are short here in Italy, each place has lots to offer. Even if you don't go into any museums, you can and should spend time in each place walking around and seeing the sights (piazzas, churches, monuments) and enjoying your meals, eating lots of gelato and just soaking in the atmosphere that is Italy.

Since you are driving up from Rome, it would make sense to make your first stop be in the area south of Siena. Get closer to Siena - maybe the Crete Senesi, take a look at San Giovanni in Poggio as a possibility - and use that as a BASE for at least 2 nights. On your first day, see Montepulciano, Pienza and San Quirico as you make your way to this area. You can have dinner in Montalcino or Buonconvento. The next day spend the entire day in Siena. Then as you move on for the 3rd-4th night, I would recommend the area between San Gimignano and Florence so that you see a bit of Chianti and San Gimignano that day. A stay at Palazzo Malaspina in San Donato a Poggio would be quite central, or at Villa il Poggiale. Use that as a base from which to visit Florence for a full day the 4th day.
On the 5th, you can either make your way to Lucca and then on to CT (I would fully skip Genoa to have more time to explore CT).... or stay inland and make your way toward Venice passing through and either stopping in Bologna or Padua, both lovely towns as well.

I highly recommend you book ahead where you're staying each night... June is high season and you might find difficulty booking last minute (selection will be more limited the longer you wait) - for hotels and B&Bs that offer just 1-3 night stays, the best location to search will be


New member
thank you so much, that is great advice between the two options below what do you suggest:
Option 1: spending the 5 nights between Rome and Pisa and see the areas you suggessted theoraly (this would mean returning the car in FLorence and training to Pisa (on 5th night perhaps) and later to Venice.
Option 2: Drive to C/T after Pisa and then to Venice (spending a night in or around CT...would you suggest returning the car in or around CT and training to Venice or return the car in Venice?

Do you have suggesstion for where I should book the car or any site (i.e. Kayak and Eurocar) ok?
Also would you suggest staying in Pisa or just visiting for a day?

Thanks again