Hi Frugalistas! We were looking forward to our trip to Tuscany and exploring all the best places to visit in Tuscany. But after a hectic trip around Normandy, once we got into the Tuscan countryside, relaxing in Tuscany seemed like the right thing to do. Rather than driving long distances from our Tuscan resort to hit all the big ticket towns like Siena and Lucca, a morning spent exploring the hill towns of Tuscany, followed by an afternoon relaxing on the terrace or by the pool of our resort seemed to be best for us. After a busy time in Florence, Rome or anywhere else for that matter, I thoroughly recommend relaxing in Tuscany as one of the best things to do in Tuscany and on your Italian vacation.
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Table of Contents
Relaxing in Tuscany: choosing where to stay in Tuscany
We spent a lot of time deciding where to stay in Tuscany. After much research we decided to stay outside any of the large Tuscan towns, and focus our Tuscany accommodation search on the hilltop towns around an hour south of Siena. Initially, we booked a hotel in Montepulciano, but after further consideration we decided to book something more rural. As it turned out this was a great decision for us. Because we wanted to drive in the Tuscan countryside as much as visit the beautiful villages in Tuscany we were certainly more focussed on small villages in Tuscany, rather than the larger towns. With a little more searching we found an amazing self contained apartment at a resort in the Tuscan countryside near to both Montepulciano and Pienza.
You can find out more about our Tuscan accommodation here >>
Exploring the hill towns of Tuscany
Despite it being early October, the best small towns in Tuscany were still very busy with tourists. What we found worked best was to head off early after breakfast to the village we wanted to visit – mainly so we could park our car somewhere sensible, but also to avoid the crowds. Then we spent the morning exploring before heading off either after lunch or in time for a late lunch back in our apartment. We learned on our first day that this was a popular area, with lots of people wanting to explore. Trying to visit Pienza at lunch time was basically impossible – nowhere to park anywhere in the town and people walking along the roads everywhere.
The only time we visited two villages in one day was the day we went to Pienza and then had lunch in the nearby, and much smaller, Monticchiello.
By arriving early, we were able to park in well located parking lots easily and then take the short walk into the village.
On this visit to Tuscany we enjoyed visiting:
Montepulciano (day 1)
Pienza and Monticchiello (day 2)
Montalcino (day 3).
Montepulciano
Montepulciano is charming but quite hilly (streets are quite steep in parts). We found plenty of free parking near the local council offices just past the tourist information office, and were thrilled to see two deer in a valley near our parking lot on our walk back to the car.
The main street of Montepulciano is called the Corso. Like many small tourist towns in Europe it is filled with souvenir shops. Local pecorino cheese and salami shops mixed with wine and other souvenirs. It was an uphill walk from where we had parked.
Coming to the main square (the Piazza Grande) there were plenty of steps to sit on for a rest to enjoy the pretty honey coloured stone buildings, including the town hall.
Just past the main square there are some wonderful views out over the Tuscan countryside – this was definitely one of the views we had come to see!
The main attraction in Montepulciano is its namesake wine. There are plenty of enoteca to taste this fullbodied, but quite supple red wine and it is readily available in supermarkets.
Pienza
Pienza is much flatter than Montepulciano, making it a much easier option for those with very young children or the less mobile. It is also much smaller. Pienza was put on the map by a fifteenth century Pope who proceeded to build a number of fancy buildings and turn it into a Renaissance architectural masterpiece, but it was the more humble offerings we particularly enjoyed.
We loved having a wander around Pienza in the early morning before it got too busy and found the views of the surrounding countryside just as attractive as those in Montepulciano.
Pienza is quite a bit smaller than Montepulciano. We found a small Co-op supermarket opposite the car park where we left our car, so after exploring the town we took advantage to stock up on very reasonably priced and drinkable Montepulciano wine and delicacies. There is no need to buy food from the souvenir shops in the old part of the village – you can get everything at the supermarket for a fraction of the price. Just make sure you bring a shopping bag or be prepared to pay for one.
Be very careful of the parking around Pienza. Many spots are designated for local residents only and fines are hefty.
frugal first class travel travel tip
Monticchiello
Monticchiello is a tiny hilltop village of some 200 people. It’s around 15mins drive from Pienza, so it makes a perfect place to visit after you have explored Pienza. Arriving in the late morning we were thrilled to find an almost empty car park – and free parking!
We originally only came to Monticchiello to have lunch at the highly rated Ristorante Daria, but found it charming. It’s the sort of village where Nonnas hang their washing out from upstairs windows and cats lounge lazily on sun warmed stone fences.
Wandering along we were surprised to have a tea towel land at our feet with a cry of “Scusa”. An elderly resident had dropped it while trying to hang it out to dry. Her son quickly appeared at the window and apologized in English as Mr frugalfirstclasstravel threw it back up. You can’t plan for experiences like that.
Ristorante Daria did not disappoint – excellent food and service, including our first taste of the famous (and famously expensive) Brunello wine. It really whet our appetites for our visit to Montalcino the home of Brunello the next day. We also tasted a local pasta, pici – which we then sought out at the supermarket to enjoy at our accommodation. It was a short, quite chewy solid pasta which was delicious.
Montalcino
Montalcino is a bit more workaday than the other villages we visited. But we were there to taste Brunello wine so weren’t fussed about the relative lack of village charm. We still enjoyed our wander around as locals did their shopping and chatted to each other in the main square. It certainly seemed more authentic than either Montepulciano or Pienza, although it was definitely not as pretty. There were still some amazing views of the Tuscan countryside from the various vantage points around the town.
Brunello wine really rules in Montalcino, to the extent that one of the main attractions is the wall of ceramic tiles in the main square. Each year the quality of the vintage is depicted on a tile by local artists.
But we had come to taste Brunello rather than celebrate the vintages, so we headed to the Enoteca di Piazza recommended by Rick Steves.
Tasting Brunello wines at the Enoteca di Piazza was certainly one of the best experiences we had on our Tuscany village visit and is one of the most efficient ways to experience wine tasting in Tuscany. Rows and rows of Brunello wines were lined up with automatic dispensers. We got our cards that are used to tap on and tap off to pay for our tastings and release our wine and then it was game on. Each bottle had a price on it, and the price per taste was also clearly labelled.
We decided to start with some cheaper options, before moving onto the more expensive choices. As pourings from the automatic dispensers were quite generous we decided to take two different wines at a time so we could try more by sharing each pour. Interestingly we found we liked the mid ranged priced wines best. While we didn’t taste any of the really expensive options the more expensive ones we tried (still over €100 a bottle) just didn’t suit our palates.
If the door out to the juliet balcony isn’t open, get the staff to open it for you to enjoy the spectacular view while you enjoy your tasting
frugal first class travel travel tip
How to get around the Tuscan villages
This Tuscany itinerary is only suitable with a car. Like much of the rural accommodation in Tuscany, our resort was quite isolated (and up a steep unpaved road). There are some local buses, but services are basic.
We used AutoEurope to research car options, and were able to find a good deal from a rental company we had never heard of, without a one way drop off fee (we had flown into Milan and picked up the car there but wanted to drop it off in Florence).
You can find your Italy car rental here >>
We found driving in Italy an interesting and different experience but not as crazy as we anticipated. The autostrada were comfortable and easy to drive on, but driving in and around the towns, and sorting out the different entry and car parking rules in the villages were somewhat complicated. If you are wanting to drive in rural Tuscany I really do recommend the Tripiamo Italy driving course which will help you learn everything you need to know about navigating Italian roads and Italian road rules. It is money well spent – especially compared to cost of a parking ticket.
You can purchase your Tripiamo Italy driving course here >>
We planned our trip based on the Val D’Orcia drive featured in Rick Steves Italy guidebook. It was essential for planning our Tuscany road trip and includes a number of other options for things to do in this part of Tuscany.
Last update on 2026-09-05 / Affiliate links / Images from Amazon Product Advertising API