Need assistance on my itinerary please...



nice forum you have here - excellent assistance so far.

i will be arriving in Rome for 8 days and departing from Pisa with my wife and another couple. we are all in mid 30's. we are a bit in the adventure site and like to organize our own trips by renting a car and getting around. So no particular problem with Kilometres ....

so i have made the following itinerary and really need some usefull comments:

Day 1: arrive in Rome at around 12:00 hrs am - (Collossseum - Forum - Piazza Spagna - Trevi - Piazza Navona) overnight in Rome
Day 2: Rome (Vatican City - Pantheon - Piazza di Spagna) overnight in Rome
Day 3: Rome (optional daily excursion to Amalfi coast - Sorento) overnight in Rome
Day 4: Leave Rome early am and drive through Saturnia to Montepulciano - Val d' Orcia - Pienza - Montalcino and arrive late afternoon at Chianti (either Gaiole or Radda) for overnight. I am currently in search of a nice farmhouse or traditional/romantic setting that we will stay for 2 nights.
Day 5: Castellina / Sienna / San Gimignano / (perhaps Voleterra) - and then stay again at the same place in Chianti
Day 6: check out Chianti, arrive in Florence all day long as a day trip and then head to Cinque Terre (arrive late night)
Day 7: Cinque Terre (all day)
Day 8: Cinque Terre / Pisa (tower of Pisa and dinner only)
Day 9: Fly out from Pisa

I think Florence deserves some more time but if you have some better suggestions please let me know. I think on Day 5 i will put some Florence....

do you have any suggestions as the accomodation in Chianti area ??? we can have a budget of max 140 euros per couple.

do you have any suggestions on the above itinerary - nothing is being booked yet so can easily be changed. we are looking for the hidden gems rather than the more touristic and crowded.

Cinque Terre by car will be a bit difficult however i cannot take out this lovely place.

any comments please ???

thanks a lot.


Further to my above message, please also advise if there are any events on this period in the area. have been in search for Andrea Bocelli but.....


The Tuscan Expert ;-)
Staff member
what are your dates?

very nicely planned, packed itinerary - it can be done, maybe you'll end up not stopping everywhere but you'll se a lot of Tuscany -- to better answer everything, what period exactly will you be here? i reread your posts but it doesn't seem you indicate what month or season! let us know so we can propose some more specific ideas, particularly about accommodation....

looking forward to hearing back soon!


Dear Lourdes,

many thanks for your reply. apologies for not mentioning dates.

my dates are 07-15 october this year.


Further to my above questions, as i will be driving through Tuscany (basis the schedule i gave you above) i would kindly request for your input as to the most scenic roads (as small as possible.... :))

For example, on the day that i will drive from Montepulciano, Pienza, San Quirico to our base in Chianti, which is the best / scenic road to take. Google maps shows SP 34 from San Quirico to Sienna (through Isola D' Arbia) and then SS 408.

isn't it better if from San Quirico continue to Montalcino and take the SS 223 and drive through the Natural Parks. ???

Same questions goes for my Chianti region tours.

if you can help me with some best itineraries that would be great.

we are looking to drive to this magnificent scenic Tuscany gravel small roads where cypress trees will be all around us..... along with old farmhouses.

thank you very much for any kind assistance you might have.


Well-known member
Hi Alex!

here I am to give you my two cents about the best routes for your trip :)

To move from the Valdorcia to Siena and the Chianti region I would suggest you to follow the first option you've already seen on Google Map.
I find it's more attractive than the other one and you'll definitely love the landscape.

If you're looking for some travel tips about the Valdorcia, I suggest you to look here:

What have you planned to see in Chianti? I'm not sure about your plans on day 5. Are "Castellina / Sienna / San Gimignano / (perhaps Volterra)" different chances?

Visit Florence in one day is a little hard, but doable. I think this article can help you to choose what to see:


Dear All,

i have managed finally to make the final itinerary.

your comments please (especially on the routes - do not hesitate to recomend any other more scenic routes)



DAY 3: ROME / S. TUSCANY (ASCIANO) (any suggestions for accomodation - agroturism),11.637955&sspn=0.276268,0.65918&via=6

DAY 4: ASCIANO / (SIENA – SAN GIMIGNANO – CHIANTI) FLORENCE (shall i stay in Greve or Castellina - they told me that Castellina is more scenic ????),11.653061&sspn=0.27546,0.65918&via=1

DAY 5: FLORENCE (i will stay at the same lodging as in day 4)

DAY 6: FLORENCE / PORTOFINO,11.27497&sspn=0.547681,1.318359

DAY 7: PORTOFINO / MONTEROSSO,9.198212&sspn=0.067684,0.164795

DAY 8: MONTEROSSO / PISA,9.661979&sspn=0.067861,0.164795

DAY 9: PISA / home....

appreciate your comments.


Well-known member
Hello Alex,

I find your routes are perfect!

For your night in Asciano, you could search for a country hotel or an agriturismo (farmhouse) in the surroundings of the city. You may start your research from this selection of accommodations here.

Greve in Chianti and Castellina are both very nice: Castellina is indeed more scenic, but Greve in Chianti has the advantage to be closer to Florence. I suggest you to look at the B&Bs or hotels in the area to better decide where to stay. Here you'll find several good options:

in Castellina in Chianti:

in Greve in Chianti: