Montepulciano as our center for Tuscany

Montepulciano is a good base for visiting the Val d’Orcia (Pienza, Montalcino and environs) but not so much for places like Assisi and Orvieto if you are using public trans.

Play around with the website Rome2Rio.com and see what transportation options are possible between locations you are interested in. Most of us would rent a car in Tuscany and Umbria, but some day tripping by bus and train are feasible. Rick Steves’ guidebook also details connections between the towns he covers. I have always found this helpful in deciding on a base location.

The nearest railhead is a half-hour away at Chiusi. There are buses serving the city, and it's an option. Still, the best way to see more of Tuscany and Umbria is by rental car.

You might want to check out Valdichiana Grand Tour. I have been researching it as an option for getting around Tuscany next trip I take. It’s a hop on, hop off bus that has several routes around Tuscany. Montepulciano is one of the stops.

You can visit Orvieto and Assisi using public transportion by taking a bus to Chiusi train station (about 30 minutes) and then a train to Orvieto (about 25 minutes) or Assisi (about 1:45). You can also take a bus to nearby Pienza, visit Siena using a combination of bus to Chiusi and train to Siena (about 1:15) or visit Cortona using a combination of bus to Chiusi, train to Camucia-Cortona (about 25 minutes) and bus up to Cortona (about 10 minutes). Most other places will be inefficient to visit from Montepulciano using public transportation. You might be able to take a taxi to and from your wine tasting and dinner if it's fairly close to town, but Uber is not a possibility. Renting a car would simplify your transportation and open up more possibilities, but it does come with the risk of traffic fines and you should never drive after drinking (very low limits).

Edit: Chiusi has some interesting Etruscan sights, so you might also consider visiting there. You would probably need to take a bus or short taxi ride up to the main part of town where the sights are located.

I agree with the posts above - when visiting Tuscany, a car rental is the best way to explore. Driving around Montepulcinao, Pienza, etc. and driving to Orvieto or Assisi is very easy from Montepulciano. If the thought of renting a car in Rome/Florence and then driving to Montepulciano causes some nervousness, consider taking the train to Chiusi and there is a Hertz just outside the train station where you can pick up your rental car (reserve it in advance). Like previously mentioned, it's onlt a 30 min drive to Montepulciano from Chiusi.

Hope this helps!!!

Do you have a good guidebook? Sounds like you could really benefit from one. Rick's "Florence and Tuscany Guidebook" would be a good place to start. He covers logistics like getting from place to place, and Montepulciano is one of the towns in the book.

Happy travels.

Thank you all for wonderful suggestions & help. You’ve given us a lot of confidence in doing this on our own.

Here's the hop on off bus Norma recommend.
Scroll all the way down for timetables, and towns to visit.

https://www.valdichianagrantour.it/en/#combo_3_tours_days