Tuscany Itinerary


New member
In September my fiance and I are going to the GReek Islands for a week for the start of our honeymoon and the secon week (technically 8 days) we are flying from Athens to Rome. Our intent is to not spend any time in Rome but rent a car and start to work our way through Tuscany over 4 days, then head to Cinque Terre and Sestra Levante area for 2 days and spend the last 2 days in Venice.

I need some help on my Tuscon itinerary. I want to make the most of our time there. We are not spending any time in Florence as we did on our engagement trip 3 years ago where we toured Lake Como, Florence, San Giamiango, Rome, the Almalfi Coast and Capri.We did this trip over 12 days. Lots of moving around but we saw a lot and loved it. We actually got angaged looking over the Piazza Michaelangelo. We love Italy!!!

WE arrive Sept 27th midday. Rent the car and drive to Orvieto and spend the afternoon and then drive to Montalcino where we will stay for 2 nights and use that as our base. Over the next 2 days, spend time in Montalcino, Sienna, and Pienza. The next day we will head more north to the Lucca area and spend some time (not sure where we will stay). Over the next two days stay either in Cinque Terre or Sestra Levante. At some point we will drop the car somewhere and use the train. We plan on taking the train to Venice.

Any advice is appreciated. Is there any small town we should add or delete etc.. Thanks for your advice.


I haven't been to Tuscany yet, but am working on my itinerary for May'14. A friend of mine highly recommends Pitigliano in southern Tuscany's Maremma region. She read about it before her trip and made a detour to visit it and absolutely loved it. Also, if you get tired of driving around, you can spend time at one of the Hot Springs. Saturnina seems to be the most popular. BTW, many trails in Cinque Terre are closed. If you were planning to hike there, you may want to check in advance whether you will have this option. Have fun!


The Tuscan Expert ;-)
Staff member
Ciao Storpey,

Sounds like you had a wonderful first trip to Italy 3 years ago and you fell in love with the country - it does have that effect on many of us ;). So wonderful to imagine you got engaged in Piazzale Michelangelo, overlooking all of Florence. Personally got asked a little further up, on the steps of San Miniato, but with an equally view of Florence :).

Since you're planning to rent the car in Rome and head up, you have two choices: head along the coast and stop in the Maremma area as Mbtravel has suggested - stopping and seeing Pitigliano, Sorano, Sovana and Saturnia for example - or driving inland as you've planned and visit the Val d'Orcia. Both are Southern Tuscany but each is one side of Monte Amiata, the mountain that marks southern Tuscany geography - Maremma to the west, the Val d'Orcia to the northeastern side. The Val d'Orcia is more what you expect of Tuscany - wide open rolling hills with cypresses and beautiful views, mixed in with vineyards around Montalcino and Montepulciano.

You can't do that and Pitigliano - there is Monte Amiata in between, just so you know. Since you're going up to CT/Sestri, maybe I'm more for doing Val d'Orcia and Siena as you've already planned.

Once you head up to Lucca, you should also see Pisa and Lucca, with a day trip to Cinque Terre. It would make sense to go with the car, and then eventually drive over to Bologna and return the car there, take the train from there to Venice.... otherwise you'd need to return to Florence or go through Milan for the train to Venice, which would add too much travel time.

AS Mbtravel has noted, right now the main trail (#2) along the coast in CT is closed - winter rains and landslides make this a yearly occurrence. But if you keep a lookout on the official park page
and check it before you come in September, it is likely many of the sections will be reopened this summer and you won't have trouble visiting them.