Best 2-3 towns in Tuscany to see countryside, drink wine, and take in the area

Be sure to have a designated driver if you intend to wine taste- the alcohol limits are much lower in Italy than in the States.
All drivers must have an IDP- required by law.

Do your homework and know how to drive in and out of Florence avoiding ZTLs. Those directions can be found with a search of this forum. You will not be driving into and parking in any of the villages- parking is in lots outside the walls

We prefer the Val d'Orcia region- Montepulciano, Pienza etc. Those are the views most think of when they are talking about Tuscany countryside
Siena is worth an overnight but parking and driving in and out of the city can be a pain. I can recommend a hotel with parking in Siena if you are interested.

Both SG and Volterra are extremely crowded and touristy.

I don't see hotels or BBs recommended
We are mother daughter and an agriturismo sounds great but I don't
want to do any cooking. Is a hotel better?

Have you searched this forum?
Agriturismos are not necessarily self catering- most offer dinner on site. We prefer to be IN a town so we can walk to dinner/drinks from our hotel

You say 4 days. Does that mean you have 3 nights for Tuscany, ending back in Florence?

Driving in Tuscany takes longer than it looks like. We stayed near Arezzo on our first trip and it took so much longer to get to Cortona than we thought it would. We ended up skipping Siena.

I'd suggest a couple of options:
1. Skip the car, train to Siena and then look into a tour to take you on your wine tasting in Montepuliciano area. This way you avoid finding parking, worry about drinking etc. Stay all 3 nights in Siena and if you need another day trip it could be done by bus.

2. If you really want a car I would focus on one area; either SG/V or M/M. If it were me, I'd train to Chiuisi and try to get the car rental from there to avoid driving in Florence, but that is just my preference. Then I"d spend the 3 nights in M/M area, with daytrips as I felt needed
Just a comment about the staying in the countryside and drinking wine. I find the towns all have lovely wine bars and then you can walk back to your hotel. I would start by looking at a few of your favourite towns on booking.com ( or in the Rick Steves book), finding a hotel you like and going from there as an option too.

You do not have to cook in an agriturismo. One of the joys of staying in a good one is the opportunity to enjoy great local food without having to leave the premises at night.

You say you see no B&Bs recommended? Where are you looking? There are hundreds, all over Tuscany.
Agree to concentrate on the Val d"Orcia. I don't know how much time you have, but I would stay in that region..
Pienza is also a lovely town.

Thanks so much for the prompt reply. I guess I meant about the BBs that I always stay where Rick recommends in his guide books but don't see any of those recs. What is the best way to find quality housing in Tuscany? Are there any you recommend?

Start by searching this forum for specific towns
Filter search by Type and Date

Use booking .com to search-use the filters for budget, amenities etc
Read the reviews there as they can only be left by actual clients

I can recommend places in Pienza, Montepulciano and Siena that all have parking

I believe the RS Florence/Tuscany guidebook will have recommendations however Rick is not a fan of Pienza (for reasons i don’t understand-it’s a lovely little town with fantastic virws and it is flat-easy to drive into/out of)

It is not wise the imbibe alcohol and driving in Italy.

Consider finding a tour. Siena is wonderful and you can do day trips from their taking tours.
Then you can drink wine.
https://www.tuscanescapes.com/day-trips
https://www.tripadvisor.com/Attractions-g187902-Activities-c63-Siena_Tuscany.html

This one only $59 each
https://www.tripadvisor.com/AttractionProductReview-g187902-d33306983-Chianti_Half_Day_Wine_Tasting_Tour_from_Siena-Siena_Tuscany.html

https://www.tripadvisor.com/AttractionProductReview-g187902-d11474899-Hidden_Castles_Chianti_Wine_Experience_Small_Group-Siena_Tuscany.html
https://www.tripadvisor.com/AttractionProductReview-g187902-d12987249-Pisa_San_Gimignano_Chianti_Day_Trip_with_Lunch_Wine_Tasting-Siena_Tuscany.html

We took a train to Chiusi and picked up a rental car there. We stayed in an agriturismo just 3 km outside of Montepulciano. It was fabulous! We had a kitchen, so we could reheat our pizza leftovers! Her breakfasts were wonderful, always a hot egg dish provided by her chickens, and fresh coffee cake that she baked. She provides dinner on your first night, so you can get checked in and not have to worry about getting out again. From there you can explore all of the Val d’Orcia for all of the Tuscan views you are wanting. We took a tour to Montalcino for the wine tasting with lunch and stopped at Pienza and Montepulciano on the way back. I would definitely recommend a driver as our lunch paired 6 different wines with our meal! We returned one day to fresh homemade doughnuts on our table, then relaxed at the pool. It was a dream.
www.agriturismolabruciata.it

Our trip to Tuscany is set for the third week of March 2026 which is not the busy season. Is this a good time to visit?

March in Tuscany is known for its “crazy” weather. Days can start out with sunshine and suddenly turn cold and rainy with unexpected showers. Some rain falls during one in three days during March.

We will spend time in Florence before Tuscany. Do you all consider visiting Sienna for a day worth it before heading to Montepulciano / Montalcino/Pienza for 3 days and taking the local wine tours.? Or would you concentrate your 4-5 days in southern parts of Tuscany?

Siena (with 1 N) is worth a full day or even an overnight. You could pick up rental car in Siena, use it for the 3 days then return it to Florence. Although you will have better rental options in Florence

From Florence- take the bus to Siena- (it drops you up in town vs train-outside of town)

Many of the wine tours leave from Siena- ToursbyRoberto.com gets excellent reviews. Not sure how many will be operating in March?
Each of the towns you have listed have multiple places offering wine tasting in town- no need to go to actual winery which mostly need appointments.

It is getting a bit late to book accommodations for March- I would get on that right away.

Following

We are flying into Rome on April 2nd. This is a few days before Easter. We are staying in Montepulciano at a lovely Agriturismo and will have that as a home base for 6 nights. We can walk to town from the place we are staying but need a car to visit Orvieto & other nearby towns. Besides Rome does anyone know where I can rent a car?? My husband is reluctant to drive out of Rome (this is our 4th trip to Italia) & he had a bad experience driving out of Rome in the past. After Montepulciano we are heading to Assisi for 2 nights and I plan to see Spoleto & Spello from there and spend time in Assisi. After that I have time until I meet the rest of my family in the north (near Milan) around April 18th. Looking for ideas on where to go from there 10th to the 18th of April??. I want another home base. Thanks. Marianna

We are flying into Rome on April 2nd. This is a few days before
Easter. We are staying in Montepulciano at a lovely Agriturismo and
will have that as a home base for 6 nights. We can walk to town from
the place we are staying but need a car to visit Orvieto & other
nearby towns. Besides Rome does anyone know where I can rent a car??
My husband is reluctant to drive out of Rome (this is our 4th trip to
Italia) & he had a bad experience driving out of Rome in the past.
After Montepulciano we are heading to Assisi for 2 nights and I plan
to see Spoleto & Spello from there and spend time in Assisi. After
that I have time until I meet the rest of my family in the north (near
Milan) around April 18th. Looking for ideas on where to go from there
10th to the 18th of April??. I want another home base. Thanks.
Marianna

Marianna- Please post your question in its own thread/subject line. You will get more responses and better targeted to your question- not JWhitt's question.

You can rent a car in Chiusi- take train from Rome. Chiusi is about a 45 min drive to Montepulciano
There is only Avis/Budget there- closed on Sunday, closed at noon on Saturday and from about 1-4 on weekdays. (same as most any other rental agency not at an airport)
You could also pick up car at FCO the drive from there is easy.

We always rent thru AutoEurope.com with No Deductible, full coverage= peace of mind.
Make sure all drivers have an IDP-required by law.
Do your homework regarding driving in Italy- ZTLs, speed cameras, tolls, parking and alcohol limits

Thank you. Appreciate your assistance