3 Idyllic towns in Tuscany to visit on your next trip to Italy

Tuscany, where picturesque vineyards roll like waves across the landscape and hills seem to stretch endlessly to the horizon, beckons with an idyllic charm that transcends time. It's a region drenched in culture, where art flourishes, and where decadent cuisine is a way of life. Within Tuscany, nestled amidst the rolling countryside, you'll find medieval towns framed by cypress trees, each offering a quintessential taste of this unique corner of Italy.

If you're seeking respite from the well-trodden paths of Siena or Florence, these charming hamlets, where the locals have mastered the art of la dolce far niente – "the sweetness of doing nothing," are waiting to be discovered. Here, we'll guide you through some of the most enchanting places where you can indulge in that art.

Here are three idyllic unusual options to visit close to Siena that keep you off the beaten track:

Montepulciano
Pienza
Montalcino

Where to Stay

During our enchanting three-night stay in Montepulciano, we embarked on day trips to explore the neighboring regions. Traveling with our 8-month-old, we were pleasantly surprised to find that all these destinations were not only baby-friendly but also accessible with a stroller. It's worth noting that Tuscany's terrain is often characterized by its charming uphill towns. However, don't let that deter you, for the more you ascend these picturesque streets, the more opportunities you have to savor the delectable local delicacies that await at the summit of your exploration.

In Montepulciano, you'll find a range of accommodation options to suit different preferences and budgets. Here are some hotel options in Montepulciano:

Luxury Hotels:

Palazzo Carletti: This elegant boutique hotel, housed in a historic palace, offers luxurious rooms, a beautiful garden, and a terrace with panoramic views of the surrounding countryside.
Palazzo Nobile di San Donato: Located in the heart of Montepulciano, this stunning hotel features opulent rooms, a wine bar, and a garden with breathtaking views. It's perfect for a romantic getaway.
La Cisterna: A charming luxury hotel set in a historic building, La Cisterna offers comfortable rooms, a wine bar, and a terrace with stunning vistas of the Tuscan landscape.

Mid-Range Hotels:

Hotel I Due Cigni: This family-run hotel provides comfortable rooms and a welcoming atmosphere. It's situated a short drive from the center of Montepulciano, offering a peaceful escape.
Hotel Panoramic: Nestled in the heart of Montepulciano, this mid-range hotel boasts cozy rooms and a rooftop terrace with fantastic views. It's an excellent choice for exploring the town.
Agriturismo Nobile: For a taste of rural Tuscany, consider staying in this agriturismo just outside Montepulciano. It offers comfortable rooms, a swimming pool, and an on-site restaurant.

Budget-Friendly Options:

La Terrazza di Montepulciano: This affordable hotel offers basic but clean rooms, and it's conveniently located in the town center, making it a good choice for budget-conscious travelers.
Meublè il Riccio: A cozy and budget-friendly option, Meublè il Riccio is situated in the historic center of Montepulciano. It provides simple rooms and easy access to the town's attractions.
Residenza Fabroni: This charming guesthouse offers budget-friendly accommodations in the heart of Montepulciano. It's a great choice for those looking for a comfortable and affordable place to stay.

Transportation

Renting a car liberates you from the confines of fixed itineraries and timetables. Tuscany's landscape is a canvas of rolling hills, vineyards, and charming hamlets, offering an endless supply of picture-perfect moments. Having a car allows you to take the scenic route, where each twist and turn presents an opportunity for capturing the breathtaking beauty of the countryside. Stop wherever you please, whether it's to admire a field of poppies or to capture the iconic cypress tree-lined winding roads that have become the stuff of postcards.

Val d'Orcia: A UNESCO Treasure:

The Val d'Orcia, a region in Tuscany, is often described as the heart of this enchanting land. This area's aesthetic beauty has been so exceptionally preserved that it has earned the prestigious designation of a UNESCO World Heritage Site. When you have a car, you can venture into this picturesque area with ease.

Val d'Orcia's Allure:

Val d'Orcia is a place of pure aesthetic delight, where rolling hills are adorned with poppy-filled meadows, and iconic cypress trees grace the winding roads. This region epitomizes the Tuscan dream, and with a car, you can immerse yourself fully in its magic. Explore its charming villages, vineyards, and iconic landscapes, all while enjoying the freedom to linger wherever the beauty calls to you.

Towns in Tuscany to visit: fairytale of Montepulciano

Montepulciano is a fairytale in Tuscany, surrounded by vineyards. The hilltop terracotta town known for its full-bodied variety of red grape is located in Southern Tuscany not too far from Siena. 665m high to be exact that is surrounded with panoramic views of Val d’ Orcia and Val di Chiana valleys.

Montepulciano makes a wonderful base for visiting other nearby towns such as Pienza, the pecorino town and the thermal village of Bagno Vignoni. The old part of the town is car free (much like many in Italy), so make sure to leave your car in a parking lot just outside the medieval walls.

Cobbled stone pathways wind up the steep town that pass numerous enoteca shops and restaurants reaching Piazza grande, the monumental square on the highest point in town. Here you will find the Palazzo Comunale the fifteenth century jewel. Stop for an espresso, visit the museum for an insight on the town's darker history or admire the beauty of the valleys below. The town dates back to the 4th and 5th century BC and is full of elegant Renaissance palaces and ancient churches. There are majestic buildings that have been worked on by many famous Renaissance artists like, Andrea Pozzo, Giuliano da Sangallo and Michelozzo.

More importantly, there are plenty of places to stop for antipasti, gelato or rustic wine bars around every corner. Shop in cozy little stores for copper pots and pans, coffee or spices and red wine. Stop for breakfast at caffé Poliziano that has been open for more than 150 years, for a blend of modern tradition that has served many famous writers and musicians in the past.

Pienza

Towns in Tuscany to visit: The enchanting Pecorino in Pienza

A town that lingers of pecorino cheese, Pienza is just 20 minutes away from Montepulciano also located in Val d’Orcia. This UNESCO recognized town is a darling little place filled with refined charm that was home to Pope Pius II. With white laundry gently swaying the breeze and oversized hydrangea bushes line doorsteps, there is a calmness in this Renaissance town.

You will find little cheese shops here, so make sure to sample a selection and stop by the main square for the airiest apricot croissants for breakfast. We sampled aged nutty pecorino with these croissants, which was a mouthwatering combination of sweet and savory. La Vecchia Bottega serves a mixture of cheeses, cold cuts and wine if you fancy a taste. Walk around the edge of the town and overlook the views at Mount Amiata in the distance. If you are here in the evening, I would recommend stopping for a glass of wine as the sun begins to set overlooking the hills while sampling on cheese and honey. Pay attention to the street names and find Via dell'Amore (street of love) and Via del Bacio (street of the kiss) to complete your heartfelt stroll.

Towns in Tuscany to visit: Montalcino, a wine lovers mecca

Montalcino is a beautiful medieval town and a mecca for wine lovers that is best explored by roaming without a plan. This town is world-famous for its renowned red wine, the Brunello di Montalcino, which is often considered the absolute Italian wine in Tuscany. The wine ages for at least 2 years in oak barrels, and for at least 4 months in the bottle. Experience wine tasting in one of the cozy enotecas and see the vineyards if you prefer an actual tour of wine production.

Just a 45 minute drive from Montepulciano, we loved the ambiance of the town; the antique stores, restaurants and overall atmosphere. We had an amazing lunch by the square on Via Giacomo Matteotti at a restaurant called Alle Logge di Piazza, enjoying some beef tartar and creamy cacio e pepe, while naturally sampling on some local wine. A stroll through the idyllic narrow walkways reveals small churches, picture worthy lanes and terracotta potted staircases. Just like in a fairytale, the Sunday church bells do their magic as we enjoy our fior di latte gelato that melts under the warm sun rays. This is what life in Tuscany is all about, that slow pace of life tucked in between gorgeous walls of rich culture.

This is the essence of life in Tuscany – a slow-paced existence tucked within walls steeped in rich culture and history. Experience the magic of these three idyllic towns that will captivate your heart and immerse you in the true essence of la dolce vita, the sweetness of life.