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Unwinding Among the Tuscan Hills: Discovering the Charm of Tuscany’s Hill Towns

Hello Savvy Travelers! We eagerly anticipated our journey to Tuscany and uncovering all the top destinations in Tuscany. However, after an intense itinerary through Normandy, settling into the tranquil Tuscan countryside seemed like the perfect plan. Instead of long drives from our Tuscan retreat to visit major towns like Siena and Lucca, spending the morning discovering the Tuscan hill towns and the afternoon relaxing on our terrace or by the pool seemed ideal for us. Following a hectic time in Florence, Rome, or virtually anywhere else, I highly suggest unwinding in Tuscany as one of the prime activities in Tuscany and during your Italian getaway.

Unwinding in Tuscany: exploring the hill towns of Tuscany View of the Tuscan countryside with vineyards and olive trees

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Table of Contents

Unwinding in Tuscany: selecting where to stay in Tuscany

We devoted considerable time to determining our accommodation in Tuscany. After thorough research, we chose to stay outside the larger Tuscan cities and concentrated our Tuscany lodging search on the hill towns approximately an hour south of Siena. Initially, we reserved a hotel in Montepulciano but later opted for a more rural setting. Ultimately, this was an excellent choice for us. Since we aimed to explore the Tuscan countryside in addition to visiting the picturesque villages in Tuscany, we were definitely more focused on smaller villages rather than the bigger cities. With a bit more searching, we discovered a fantastic self-contained apartment at a resort in the Tuscan countryside, conveniently close to both Montepulciano and Pienza.

Unwinding in Tuscany: exploring the hill towns of Tuscany View from a hilltop over a valley Tuscany Italy
The view from our resort

Get more details about our Tuscan lodging here >>

If you prefer a hotel or town location, check out this Montepulciano hotel we initially considered >>

Unwinding in Tuscany: exploring the hill towns of Tuscany Swimming pool in a Tuscan resort Tuscany Italy

Discovering the hill towns of Tuscany

Even though it was early October, the most charming towns in Tuscany were still bustling with tourists. We found that leaving early after breakfast for our chosen village worked best—both to secure sensible parking and to avoid the throngs of visitors. We spent the mornings exploring, then either left after lunch or headed back for a late lunch at our apartment. On our first day, we discovered that this area is very popular, attracting numerous explorers. Attempting to visit Pienza at midday was nearly impossible—no parking available, and pedestrians crowded the roads.

Unwinding in Tuscany: exploring the hill towns of Tuscany Laneway in Montepulciano with garden and houses in the background
It’s worth exploring beyond the main thoroughfare in Montepulciano

The sole occasion we visited two villages in one day was the day we explored Pienza and then had lunch in the nearby, much smaller, Monticchiello.

By arriving early, we could easily park in convenient parking lots and enjoy a short walk into the village.

During this stay in Tuscany, we explored:

Montepulciano (day 1)

Pienza and Monticchiello (day 2)

Montalcino (day 3).

Montepulciano

Montepulciano is delightful but quite steep (streets are fairly inclined in some areas). We discovered ample free parking near the municipal offices just past the tourist information center and were thrilled to spot two deer in a valley near our parking area on our walk back to the car.

Unwinding in Tuscany: exploring the hill towns of Tuscany Montepulciano skyline
Montepulciano skyline

The principal street in Montepulciano is known as the Corso. Like many quaint tourist towns in Europe, it is lined with souvenir shops. Local pecorino cheese and salami shops intermingle with wine and other mementos. Our journey from our parking spot was uphill.

Reaching the main square (Piazza Grande), numerous steps provided a welcome rest to enjoy the lovely honey-colored stone structures, including the town hall.

Unwinding in Tuscany: exploring the hill towns of Tuscany Square in Montepulciano Tuscany Italy view of the front facade of the townhall
The main square of Montepulciano

Just beyond the main square, breathtaking views of the Tuscan countryside awaited us—definitely one of the vistas we came for!

Unwinding in Tuscany: exploring the hill towns of Tuscany View from Montepulciano vineyards and olive groves Montepulciano View of San Biagio church from Montepulciano
Olive groves and the San Biagio Church from Montepulciano

The primary highlight in Montepulciano is its namesake wine. Numerous enoteca allow tastings of this robust yet smooth red wine, which is readily found in supermarkets.

Pienza

Pienza is significantly flatter than Montepulciano, making it a much easier choice for those with very young childrenor the less inclined to move. It is also considerably tinier. Pienza gained prominence thanks to a fifteenth-century Pope who commissioned various grandiose structures and transformed it into a Renaissance architectural gem, but it was the more modest offerings that captivated us.

We thoroughly enjoyed meandering around Pienza in the early hours before it became too crowded and discovered that the vistas of the surrounding landscape were equally as enchanting as those in Montepulciano.

Main street in Pienza with a souvenir shop Relaxing in Tuscany: exploring the hill towns of Tuscany
Morning in Pienza – it’s highly recommended to arrive early in Pienza to enjoy the peaceful streets

Pienza is noticeably smaller compared to Montepulciano. We discovered a small Co-op supermarket across from the parking area where we left our vehicle, so after exploring the town we took the opportunity to stock up on affordably priced and drinkable Montepulciano wine and treats. There’s no necessity to purchase food from the souvenir stores in the historic part of the town – you can get everything at the supermarket for a much lower cost. Just ensure you have a shopping bag or be ready to buy one.

Relaxing in Tuscany: exploring the hill towns of Tuscany Yellow flowers in front of a traditional building in Pienza Tuscany Italy

Be highly cautious about the parking regulations around Pienza. Numerous spots are reserved for local residents only and penalties are significant.

frugal first class travel travel tip

Monticchiello

Monticchiello is a minuscule hilltop village inhabited by about 200 people. It’s roughly a 15-minute drive from Pienza, making it an ideal destination to explore after visiting Pienza. Arriving in the late morning, we were delighted to find an almost vacant car park – and free parking!

Initially, we came to Monticchiello solely to have lunch at the highly acclaimed Ristorante Daria, but we found the village delightful. It’s the kind of place where Nonnas hang their laundry from upstairs windows and cats laze contentedly on sun-drenched stone walls.

Relaxing in Tuscany: exploring the hill towns of Tuscany Steps with pot plants on each step with creepers on the wall Montechiello Tuscany Italy

As we strolled along, we were startled by a tea towel that landed at our feet with an exclamation of “Scusa”. An elderly resident had accidentally dropped it while trying to hang it out to dry. Her son quickly appeared at the window and apologized in English as Mr frugalfirstclasstravel tossed it back up. Experiences like that can’t be planned for.

Ristorante Daria exceeded our expectations – excellent food and service, including our first encounter with the renowned (and famously costly) Brunello wine. It really piqued our interest for our visit to Montalcino the following day, the home of Brunello. We also tried a local pasta, pici – which we later bought at the supermarket to savor at our accommodation. It was a short, rather chewy solid pasta that was delicious.

Montalcino

Relaxing in Tuscany: exploring the hill towns of Tuscany Square stone belltower Montalcino Tuscany Italy

Montalcino is slightly more utilitarian compared to the other towns we explored. But since we were there to sample Brunello wine, we were not too concerned about the relative lack of village charm. We still enjoyed our stroll around as locals shopped and chatted in the main square. It certainly felt more genuine than both Montepulciano and Pienza, although it wasn’t as picturesque. Nevertheless, there were still some splendid views of the Tuscan countryside from various vantage points around the city.

Brunello wine truly dominates Montalcino, to the extent that one of the main attractions is a wall of ceramic tiles in the primary square. Each year, the quality of the vintage is depicted on a tile by local artists.

Relaxing in Tuscany: exploring the hill towns of Tuscany Painted tiles showing best Brunello wines Montalcino Tuscany Italy

But we had come to taste Brunello rather than celebrate the vintages, so we headed to the Enoteca di Piazza recommended by Rick Steves.

Sampling Brunello wines at the Enoteca di Piazza was undoubtedly one of the finest experiences we had on our Tuscany village visit and is one of the most effective ways to enjoy wine tasting in Tuscany. Rows upon rows of Brunello wines were available with automatic dispensers. We received our cards, which 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 was labeled with a price, and the cost per taste was also clearly marked.

Relaxing in Tuscany: exploring the hill towns of Tuscany Bottles of Brunello wine in a wine tasting bar Montalcino Tuscany Italy
Yes, the prices of the top shop are in the triple figures, but you don’t need to spend that much for a good bottle

We opted to begin with more affordable choices before progressing to the pricier selections. Given that the automatic dispenser servings were generous, we decided to sample two different wines at a time so we could try more by sharing each pour. Interestingly, we found that we preferred the mid-priced wines the most. While we didn’t taste any of the very costly options, the more expensive ones we tried (still over €100 a bottle) just didn’t suit our tastes.

Relaxing in Tuscany: exploring the hill towns of Tuscany Two glasses of Brunello red wine overlooking Montalcino

If the door to the juliet balcony isn’t open, request the staff to open it so you can relish the stunning view while enjoying your tasting

frugal first class travel travel tip

Navigating the Tuscan Villages

This Tuscany travel plan is solely convenient with a vehicle. Similar to many of the countryside lodgings in Tuscany, our resort was pretty secluded (and located up a steep unpaved path). There are a few local bus services, but they remain quite limited.

We utilized AutoEurope to explore car rental options, finding an excellent deal from a car rental company we were unfamiliar with, with no additional fee for one-way drop-off (we had flown to Milan and picked up the car there but aimed to return it in Florence).

You can find your Italy car rental here >>

Our experience driving in Italy was intriguing and different but not as chaotic as expected. The autostrada were comfortable and manageable, though driving in and around the towns, and understanding the various entry and parking regulations in the villages, was somewhat challenging. If you plan to drive in rural Tuscany, I highly recommend the Tripiamo Italy driving course, which provides comprehensive information on navigating Italian roads and traffic rules. It’s a worthwhile investment, particularly when compared to the cost of a parking fine.

You can purchase your Tripiamo Italy driving course here >>

Our trip was organized around the Val D’Orcia drive detailed in Rick Steves Italy guidebook. It was vital for planning our Tuscany road adventure and includes numerous other suggestions of activities in this region of Tuscany.

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