Help Plan 2 week holiday in Tuscany


New member
My wife and I are planning a 2 week holiday mid September to see and experience Tuscany. From my research here are the things that interest us. I would appreciate help in choosing the more important sights (and dropping the minor ones) as well as helping plan the trip i.e. where to stay etc. I am thinking I will arrive in Florence, sightsee Florence for two days by foot and then rent a car to travel around Tuscany. I am hoping I could pick a couple of places to stay so we are not packing/unpacking each day. We are fit and love walking.
A big THANK YOU in appreciation! Grazie!!
1. Etruscan villages: Sovana, Pitigliano, Viterbo, Tarquinia
2. Monasteries: Assisi, Perugia, Cortona, Santuario Della Verna, Poppi, Monastero & Sacro Eremo Di Camaldoli, Abbazia Di Monte Oliveto Maggiore
3. Piero Della Francesca's paintings: Urbino, Passo Di Bocca Trabaria, Sanse Polcro, Monterchi, Arezzo
4. Wine Tour: Castello Di Varrazano, Greve in Chianti, Badia a Pasignano, Panzano, Castello di Ama, Montalcino, Montepulciano
5. Tuscan Landscapes: Siena, Pisa, San Quirico, Pienza, Osteria La Porta, Chiusi, Orvieto


Well-known member
Divide up the vacation


Places to stay - Casentino is one of my all time favorite areas of Tuscany (could be because I lived there for several years so I am biased) but a stay there would definitely give you access to the monasteries and a trip to Arezzo (for the paintings) as well as a a great panoramic route towards Assisi ecc.
Bibbiena is a central area - however I have also visited Borgo I Tre Baroni and they are a panoramic position and an onsite restaurant.

Val d’Orcia would be a great alternative - it’s a definite scenery completely with its own special charm.

Then you could also look towards the western edge of Chianti its not the heart of the “touristy” area but definitely worthy of quite a few photo opportunities.

Buon Viaggio,
Donna Denise


The Tuscan Expert ;-)
Staff member
I would organize by area and definitely divide into two bases - and seeing you're interested in the monasteries, I would do one base in Casentino and another in Val d'Orcia. From both you can do day trips further afield -- from Casentino into Chianti, from Val d'Orcia to southern Maremma (where you'll find Pitigliano, Sovana). Some of the places you have listed are no longer in Tuscany but being not far from the Tuscan border, you can also include - just plan to do day trips out of them (Assisi + Perugia, for example).

I agree, do Florence first and only rent car once you're ready to leave and explore the rest of the region! No need for car in Florence.


New member
Hi Lourdes & Donna Denise

Thank you for your comments.Researching via Michelin maps, here is a first cut itinerary I have drawn up. Please take a look and give me your comments on doability as well as whether I am picking the right spots to stay, the travel sequence etc. I am also assuming that one way rental cars can be had from Rome airport that can be dropped off in Florence without a significant upcharge. If not, the whole itinerary needs to be reworked.



9/10 Rome-Viterbo (100Kms) Stay at: Viterbo

9/11 Viterbo-Tarquinia(44Kms)



Sovano-Orvieto(54Kms) Stay at: Orvieto

9/12 Orvieto-Chiusi(54 Kms)

Chiusi- Montepulciano (24Kms) Stay at: Montepulciano

9/13 Montepulciano-Pienza (13Kms)


Montalcino – Montepulciano (37Kms) Stay at: Montepulciano

9/14 Montepulciano- Siena (65 Kms)

Siena-Abbasia Maggiore(38 Kms)

Abbasia Maggiore – Montepulciano (38Kms) Stay at: Montepulciano

9/15 Montepulciano- Assisi (90 Kms)

Assisi – Perugia(27 Kms)

Perugia - Montepulciano (66Kms) Stay at: Montepulciano

9/16 Montepulciano- Castello di Ama (102Kms)

Castello di Ama – Panzano(7Kms)

Panzano – Badia (3Kms)

Badia – Greve in Chianti (5Kms) Stay at: Greve in Chianti

9/17 Greve – Pisa (109 Kms)

Pisa – Greve(109 Kms) Stay at: Greve in Chianti

9/18 Greve- Cortona (110Kms)

Cortona _ Arezzo (30Kms)

Arezzo – Monterchi (29Kms)

Monterchi – Sansepolcro (15Kms) Stay at: Sansepolcro

9/19 Sansepolcro – Santurio della Verna(32Kms)

Santurio della Verna – Poppi (29Kms)

Poppi – Eremo di Camaldoli (17Kms)

Eremo di Camaldoli- Florence (66Kms) Stay at: Florence (Return Car)

9/20 Florence

9/21 Florence

9/22 Florence –Rome (Train & Back Home)

I have a spare day. Which days would seem to be a stretch and would be good to spread out


Well-known member


it's a lot of driving but it is also a rather complete itin.

If anything I would suggest not doing Pisa from Greve, but rather do it from Florence via train - or even invest in an organized tour. Pisa is a lovely city and it certainly has much to offer however, what mostly happens is you go just to see the tower (remember to reserve your ticket if you want to go up ... space is limited)

anyway - visiting the tower and the square is really a half day trip - you could easily make it a trip from Florence, relax on the train and then free up a little bit of time from driving.


Donna Denise


The Tuscan Expert ;-)
Staff member
Seems like a great, complete itinerary for 2 weeks. To cut down on some driving:

-- Maybe I would do Assisi and Perugia from Orvieto before heading further north to Montepulciano. Just to not be backtracking.

-- I would do Arezzo and Cortona after Montepulciano before heading to Greve. Then from there head to Florence to return car.

-- Do as Donna suggested and do Pisa from Florence, spending that day in Greve and in Chianti and driving around the hill towns in the region (Castellina, Panzano, San Donato in Poggio, Radda).

You can do one-way rentals, not sure on much the difference will be on cost - check here: