7 Nights in Tuscany - How would you spend it?

Will you have a car? Do your plans included visiting Florence and Siena, or just the Tuscan countryside?

Do research on Fall harvest festivals that will be held the times you plan to be there. Visiting a festival would be a great day.

Pienza is a great location. I can see a day in Montepulciano. San Gimignano/Volterra would also be a great day trip. Find a winery and do a food and wine pairing for lunch or dinner. Even Cortona is within reach.

If you love Gregorian chant, you will be close to the Monte Oliveto Maggiore Abbey. Evening Vespers are open to the public and celebrated in Gregorian chant. We spent the afternoon at the abbey, went for dinner, then returned for Vespers.

It sounds like a wonderful trip. We like to travel like you, nice and relaxed.

Nice suggestions DougMac. With 7 days in Tuscany , the couple can also take some day trips to the Chianti region and explore some villages there.

Read a different guide book. Rick writes for Americans who want to maximize their sites in the short limited vacation days Americans seem to have. 7 days in Tuscany could be a relaxing luxury if you are just staying west of the main highway. If you want to encompass all of Tuscany then it is a road trip; not memorable experiences.
Siena main square is worth a number of hours of people watching and eating gelato. Then wander over to the amazing duomo. Get lost in the back streets.
There are old bath downs very close to Pienza. In the middle of the day it could be you and a couple of town dogs lazing around the old baths. Bagno Vignoni is one we visited.
The abbey of Sant-Antimo was an unexpected joy in Montalchino. It is a simple abbey, but they play Gregorian chants and if you are lucky you will time it to attend the chants done live. It is a short stop enroute to something else.
Hit the back roads from your agriturismo for little hamlets. Stop in the bar for a drink or a coffee.
Take cooking classes or given that you are going in October; there may be wine harvesting and grape stomping going on.
Everyone's pace of 'comfortably do in one day' is subjective. I may group activities together for proximity, but I never assume I can do them all.

As an addition, check out Frances Mayes (Under the Tuscan Sun) other books. She has written a few that could be considered travelogues but it has been a while since I read them so not sure she covers that area of Tuscany or not. I read them with a map nearby so I could plot their paths. She might have written a book on travel around Lake Trasimeno which is east of Pienza.
If you want off the beaten path, just do that - drive off the beaten path. Get off the 2 main highways and wander.
EDIT - other replies while I was typing. The abbey I mention is not the same as the one mentioned above. I heard the one above can become quite crowded.

Just go with a place to stay and no plans of any kind. Your trip to the region will come to you as the days go on. Your host in the agriturismo will also guide you on what's going on in the days ahead. They might even cook for you.
We often roll with the flow.

All the advice looks good and from folks experienced I travel throughout Toscana. I think some time (say a full day) exploring some of the towns in the Chianti region sounds great. Being based in Pienza you’re also very close to Montalcino - Brunello di Montalcino is one of the best Italian wines (that and Barolo in Piedmont- where I’m staying a few days in August - are referred to as King of Italian wines). Check out a winery in Montalcino area - Rick recommends some. I would also agree with the writer who suggests getting another guidebook. My wife and I often quote “the Bible according to Rick” and we love his humorous and subjective writing style. Still, as long as you’re in this region, I would check out Lonely Planet. I just purchased a pdf download do their 2018 Italy book (I love actual paper books but Lonely Planet is too big and heavy), and it’s currently available at half price.
A region of Tuscany that is not covered by Rick but worth exploring especially in October is the Maremma in the southwestern part of Tuscany (I’m a bit biased because my Italian grandparents both came to the US from Isola del Giglio off the Maremma coast). The Citá del Tufo area, especially the town of Pitigliano, is worth exploring. In the other direction, Siena is a must see but I would recommend getting there a little later in the afternoon and stay through dinner. Like Florence, the tourist crowds in Siena can be oppressive from mid morning through mid afternoon. Volterra and Lucca are two other towns that I would definitely experience. If you’ve never done Pisa/Leaning Tower you could plan on spending most of a day in Lucca where there is a beautiful park like setting with a large bike path on the walls. If you have a car get there in the morning, explore the town, grab lunch at Da Leo, then take the bus to Pisa (goes straight from in front of the train station in Lucca directly to a stop right outside the Piazza dei Miracoli, where that falling Tower resides. Spend an hour or so there, grab an espresso and take the bus (45 minutes or so) back to Lucca. Drive back in time for a late dinner at your agriturismo.

Definitly go for an agriturismo and live the tuscan dream for a week. I won't mention "off the beaten path things". I wonder if that exist in Tuscany
-Florence is part of Tuscany, I wouldn't miss it of course. You need at least 2 days in Florence especially if you like museums.
Gallereia dell'Academia and uffizi are the most obvious when you have limited time
-Volterra and San Gimignano for a day. Try to see San Gimignano either very early or after 4pm. Much less crowded and so gorgeous when there's just a normal crowd. You can add small Monterigionni for an hour if you are a quick tourist.
-Sienna for a full day
-Pisa and Lucca for a day
-Montepulciano and Pienza for a day
-Montalcino, Sant'antimo abbey and even Monte oliveto Maggiorre for a day
-Chianti region for a day
-I was able to fit san galgano abbey, this fantastic ruin abbey on my way back from Sienna or Volterra. This is more off the beaten path as it's not very crowded, but makes superb pictures

My preferred surrounding is the san quirico d'orcia area and especially the road between San Quirico, Pienza Montepulciano. The SP148.
Montichiello rows of cypresses
I had an agriturismo there, podere cunina, it was heaven.
Have fun!
Claude

Seriously - you guys are the best! I cannot believe how many great ideas you have given me. Please keep them coming.

For some reason, abbeys and Gregorian chants were not on my radar. I have to admit to doing a Google search and listening to them this afternoon. Amazing! What a great opportunity to just do something different.

Assuming you'll have a car and if Etruscan history interests you, consider combining Chiusi with Montepulciano. I'd go to Chiusi in the morning, see the museum, do one of the underground tours (there are at least 2), visit the nearby tombs (requires reservations) and maybe grab lunch before heading back to Montepulciano. The drive from Montepulciano to Pienza isn't long, so you could even stay for dinner if you wished. If you want to visit the Etruscan tombs near Chiusi, you might ask your agriturismo hosts to call as the person who answers the phone at the museum and takes the reservations may not speak English. That's what happened to me, but luckily I knew just enough Italian to successfully reserve.

I second the suggestions to combine the Abbey with Montalcino. Very tranquil place.

We are doing 7 nights in Tuscany as well, but in early July. At current time we're planning 3 nights in Volterra (we prefer staying in towns to the countryside) from where we can visit San Gimignano, Certaldo and maybe another town. Then 3 nights in Montepulciano, stopping in San Quirico on the way. From Montepulciano we plan on visiting Pienza, Montichiello and Cortona. Then one night in Orvieto where we'll return our car. We'd like to hit Pitigliano on our way to Orvieto, but not sure if time will allow.

Figure you can visit 2 towns a day. Some require a full day, on occasion you can do 3 if they're close together.

Try this for another unusual experience. It's about 1H15m from Pienza.

https://maremma-tuscany.com/saturnia/le-cascate-del-mulino/

Pack a picnic, some nice wine and water shoes and towels.

Note...DON'T wear jewelry!!

Close by are Saturina and Pitigliano.