We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.


Wantagh, New York
Level Contributor
2,347 posts
104 reviews

Would like to split my week between 2 locations from where we will do day trips. Towns we will want to see hopefully are Cortona, Assisi, Montepulciano, Pienza and Montalcino and maybe Chianti and places in between. Any suggestions for good central locations that will be easy in and out for our day trips and then a place at night for dinner. Thanks!

Best Seller
Tuscany in One Day Sightseeing Tour
7,455 Reviews
from US$105.50*
Best Seller
Cinque Terre Day Trip with Transport...
804 Reviews
from US$105.50*
Best Seller
Cinque Terre Hiking Day Trip from...
3,429 Reviews
from US$105.50*
5 replies to this topic
Saint Marys, Ohio
Level Contributor
8,955 posts
44 reviews
1. Re: Tuscany/Umbria

If you stay in Montepulciano, it would be about a 70 minute drive to Assisi, about 45 minutes to Cortona, and Pienza and Montalcino would be short drives. Siena would be about an hour’s drive and San Gimignano would be about 90 minutes. They are in the Chianti area.

Adelaide, Australia
Level Contributor
33,634 posts
17 reviews
2. Re: Tuscany/Umbria

Route planner www.viamichelin.com

Non EU citizens require an International driving permit for Italy, contact the AAA.

Read Top Questions "Driving in Italy"

www.italia.it/en/discover-italy www.discovertuscany.com

Level Contributor
8,648 posts
1,135 reviews
3. Re: Tuscany/Umbria

Montepulciano is a great base to see both Val D’Orcia and Umbria. We visited Umbria on a separate trip, but it is very easy to reach Lago Trasimeno and Assisi from Montepulciano. We stayed at delightful Relas Villa Grazianella very close to Montepulciano and had all our dinners there simply because I cannot think of a restaurant where we could have dined better.


Edited: June 11, 2018, 10:52 am
Montepulciano, Italy
Destination Expert
for Tuscany
Level Contributor
9,007 posts
7 reviews
4. Re: Tuscany/Umbria

Absolutely, you've got it, southern Tuscany on the Umbrian border and Montepulciano certainly ticks that box. All the places on your list can be explored easily but I would throw in Orvieto too (separate day, possibly half) and combine Arezzo with Cortona. Just thinking out loud early in the morningwhilst waiting for the kettle to boil you could:

1. Cortona / Arezzo

2. Day exploring Montepulciano / Pienza

3. Longer day going down to Assisi

4. Quieter day driving up into the Chianti

5. Even quieter day just leisurely driving around the Val d'Orcia (include San Quirico, Montalcino and Bagno Vignoni)

6. Half day down to Orvieto

7. Quiet day hanging out somewhere

Though this is far from definitive list as there are many more very pretty villages to explore, these are possibly just the highlights. Now I must go and make my tea.

Level Contributor
8,648 posts
1,135 reviews
5. Re: Tuscany/Umbria

Orvieto - no doubt!!! It would be so sad to miss one of the most beautiful cathedrals in the world with immortal frescoes of Lica Signorelli in majestic Cappella di San Brizio.


Reply to: Tuscany/Umbria
Get notified by e-mail when a reply is posted