Travel Guide to the best things to do in Montepulciano area based on our own experience. All you need to know to make the most of your stay in Montepulciano area: the best things to see, the best day trips, my recommendations for restaurants, accommodation, tours and experiences, based on my own travels.
When people dream of Tuscany, they often dream of the unhurried, deeply beautiful, rolling hills and cypress trees version of it they see in travel brochures, a version of Tuscany where life is easy, food is genuine, nature is beautiful and art is all around you.
I know this well and this is exactly what keeps me coming back to Tuscany or, should I say, what keeps me coming bank to the specific part of it called Val d’Orcia and one of its main towns: Montepulciano!
Montepulciano is my favorite mall town in Tuscany and an absolute delight.
Perched high on a hilltop with views that seem to go on forever, it has all the things we most commonly associate with small Tuscan towns: meandering medieval streets with flowers at the windows and laundry drying in the sun, beautiful architecture, wonderful, real food coming from the local land and, perhaps most famously, some of the finest wine in Italy, the Nobile di Montepulciano.
I am very much not a small town gal, I am from Rome and I thrive in big centres, but let me tell you honestly: I make an exception for Montepulciano because it truly is beautiful and its position is also stunning, since it overlooks jaw droopingly beautiful countryside dotted with stunning towns.
Pienza and its extraordinary pecorino are a short drive away. Montalcino and the great Brunello vineyards are close.
Siena is only a short drive away and, in the other direction, the thermal springs of Bagno Vignoni and Bagni San Filippo offer one of the most magical and unexpected experiences in the whole region.
To say that I adore this area is an understatement.
During the pandemic, when travel finally opened up again, this was the first places we came to: we got a place in the countryside and spend days eating simple, genuine meals as the breeze caressed us, the bees buzzed among the wild flowers and the kids run free and jumped in the pool.
It is one of the closest places to heaven we have ever been to and one we always return with great pleasure. This is my guide to making the most of a stay in Montepulciano and surrounding area.
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Travel guide to the Montepulciano area TL;DR
Montepulciano is one of the most beautiful hilltop towns in Tuscany, famous for its Vino Nobile wine, stunning architecture and spectacular views of rolling hills and valleys
The area around it is among the most beautiful countryside landscape in all of Italy: Val d’Orcia, Pienza, Montalcino, Bagno Vignoni and Siena are all within easy reach
It is an ideal base for people who want to slow down, drink wonderful wine, explore gorgeous countryside and visit some of Italy’s most extraordinary small towns
The best and only way to properly explore this area is by car. I recommend renting through Discover Cars which lets you filter by size, deposit and card type. Rome and Florence are both excellent pickup and drop off points.
The best accommodation option here is a country property or agriturismo in the surrounding hills, so you will wake up to views that make you want to stay forever and genuine homemade breakfast. Please be aware that for a stay in the countryside having your own car is paramount.
My favourite experiences in this area are wine tasting in the underground cellars, a morning at the thermal springs, exploring the Val d’Orcia by car, and cooking classes at a local farm
The best seasons to visit are spring (April–June) and autumn (September–October). If you have kids, summer is also a good option as this is pool season: if coming in summer however, plan your days around staying in the house/ pool during the hottest hours of the day and leave exploring to late afternoons or early mornings as the hear is intense!
Where to stay near Montepulciano
My shortlist of places to stay in the Montepulciano area:
| Name of Accommodation | Amenities / Activities on site | Meals |
|---|---|---|
| Terre di Nano | Stunning outdoor pool, vineyard, olive grove. Wine tasting, cooking classes, additional activities in the area can be arranged on demand. Self catering private kitchen | Breakfast and dinner |
| La Pievina | Stunning outdoor pool, BBQ facilities, self catering private kitchen | Breakfast |
| La Lupaia | Stunning outdoor pool, luxury boutique hotel feel, cooking classes, wine tasting. Additional activities in the area previous arrangement | Breakfast, restaurant on site |
| Podere Fontecastello | Outdoor pool, large garden, self catering private kitchen | Breakfast available |
| Agriturismo Castello La Grancia | Castle setting, outdoor pool, large garden, kids’ playground | Breakfast |
| Agriturismo Podere Sanguineto | Outdoor pool, large garden, spa, wine tasting, cooking classes, pic nic with local products, kids playground | Breakfast, restaurant on site |
A note on accommodation: As you may have noticed, all my favorite accommodation is in the countryside rather than in the town itself. This is because in the good season, the views, the quiet, and the sense of immersion in the Tuscan landscape are a huge part of what makes staying here so special for me, and most of the best experiences in the area are a short drive away regardless of where you base yourself.
Best organised classes and experiences near Montepulciano
The best things to do in Montepulciano and surrounding area
Visit Montepulciano town
Any stay in this area for me begins with a visit to Montepulciano itself, a beautiful and quintessential Tuscan town full of charm and beauty made of brick buildings, cascading flowers, meandering roads and sweeping views.
I have a full guide to Montepulciano town here, covering all the best things to see and do.
It has quite a lot in it: the beautiful corso, Piazza Grande (one of my favorite piazza in Italy!), the underground wine cellars, the Temple of San Biagio just outside the walls, and much more, so I recommend you give it a read!
Explore the Val d’Orcia and Val di Chiana
Montepulciano overlooks two stunning areas of Tuscany: Val d’Orcia and Val di Chiana.
The Val d’Orcia is one of the most beautiful landscapes in the world, a UNESCO World Heritage site of rolling golden hills, cypress-lined roads, medieval towers and tiny fortified villages that look exactly as they did centuries ago. Val d’Orcia is the place most photos with cypress trees come from!
I have a full guide to the Val d’Orcia here, but in terms of the highlights within easy reach:
San Quirico d’Orcia (click to read my guide), a beautiful small town with a wonderful Romanesque church and the famous Horti Leonini, a stunning Renaissance garden that is free to visit and one of the most peaceful spots in the whole valley.
Bagno Vignoni (click to read my guide), one of the most peculiar and enchanting villages in Tuscany, a tiny hamlet whose main square is not a piazza but a large Renaissance thermal pool, steaming gently in the cool morning air.
You cannot bathe in the central pool but the village is extraordinary to see, and bathing facilities are available nearby. A short stop here is one of the most memorable things you can do in the whole area.
Monticchiello (click for my guide), a tiny, perfectly preserved hilltop village that few tourists reach, all stone alleys, ancient walls and views over the valley. Worth a detour and lovely for a local lunch.
Val d’Orcia road itself: the drive along the SP146 between Pienza and San Quirico, with its famous cypress-lined avenues and rolling hills, is one of the iconic images of Tuscany. Drive it slowly, stop often, and photograph it at golden hour if you can.
Val di Chiana is maybe less known as a whole but is home to many stunning and well known landscapes and towns such as stunning Cortona, easy to reach from Montepulciano and well worth a day trip.
Visit Pienza
About 15 minutes from Montepulciano, Pienza (click for my guide) is one of the most extraordinary small towns in Italy.
It is Renaissance town commissioned in its entirety in the 15th century by Pope Pius II, who wanted it to be an examples of a ‘perfect town’ according to humanists standards.
Indeed, the result is pretty spectacular: Pienza has a beautiful main square, a stunning palace, views over the Val d’Orcia that are simply unforgettable and a mellow, settles vibe that makes you think ‘wow, this is indeed pretty prerfect!’.
Pienza is very much picture perfect and often chosen for wedding photos so don’t be surprised if you stumble upon wedding parties here!
Pienza is also the home of the famous pecorino di Pienza, sheep’s milk cheese aged in various ways and the shops lining the main street are a wonderful place to taste and buy it. Even a short stop here is very rewarding.
Visit Montalcino and taste Brunello
About 30-40 minutes from Montepulciano, Montalcino (click here for my guide) is one of the great wine destinations of Italy and a beautiful town in its own right, a compact medieval hilltop village with an impressive 14th-century fortress and spectacular views.
It is famous above all for Brunello di Montalcino, one of Italy’s greatest and most celebrated red wines, aged for years before release.
Tasting it at one of the local estates, or even just in one of the town’s excellent wine bars, is one of those experiences that stays with you.
The town is small and easily visited in half a day; combine it with a winery visit in the surrounding hills and a long lunch and you have a perfect day. Good ones are: Podere Le Ripi, Matrojanni, and Castello Tricerchi
Soak in the thermal springs
This is one of the most wonderful and unexpected experiences the area has to offer, and one that many visitors don’t know about until a local tells them. Fortunately, you have me!
The hills around Montepulciano are fed by ancient hot springs, and two in particular are within easy reach and absolutely worth a visit.
Bagni San Filippo is a free outdoor thermal site in the forest, about 30-40 minutes from Montepulciano.
Its most spectacular feature is the Balena Bianca (the white whale) a dramatic white limestone formation created over centuries by the calcium-rich thermal water, from which a warm waterfall flows into natural pools below.
It is one of the most magical natural sites in Tuscany, genuinely unlike anything else.
You can simply turn up, walk through the woods and step into the river.
Bagno Vignoni (as mentioned above in the Val d’Orcia section) also has a proper thermal spa facility, if you prefer a more structured experience with pools, treatments and facilities.
Both are brilliant in any season but particularly lovely in autumn and winter, when the steam rising from the water into the cool air creates an almost otherworldly atmosphere.
Go wine tasting: Vino Nobile di Montepulciano e Rosso di Montalcino
The Vino Nobile di Montepulciano DOCG is one of Italy’s finest red wines: made from Sangiovese, it is powerful and elegant and goes exceptionally well with the earthy flavors of the local cuisine.
There are several ways to go about wine tasting in Montepulciano, all valid. For instance, you can choose between:
The underground cellars in town, historic cantine in the town of Montepulciano itself. These are vast, ancient underground cellars now open to the public and perfect for an easy yet rewarding tour and tasting experience
Wine shops in town: in Montepulciano, wine shops are ubiquitous and they serve and sell wines from the wineries of the area; they are basically their outposts in the town, so it is not a step down for getting it from the winery itself, just an easier option logistically!
Wine estates in the surrounding hills: for a more complete experience, a visit to one of the estates outside the town combines a vineyard walk, cellar tour and tasting in a beautiful countryside setting. Not all estates offer this as they are very much focused on production in this area, but some do and are worth the drive. Some also have outstanding restaurants.
Places I recommend you consider are: Podere Le Ripi, Matrojanni, and Castello Tricerchi Antinori La Braccesca, Avignonesi and Salcheto
Visit Siena
About an hour or so from Montepulciano, Siena needs no introduction: it is one of the most beautiful cities in Italy and a wonderful day trip from this area.
Siena’s extraordinary medieval center, the vast shell-shaped Piazza del Campo and the breathtaking striped Duomo especially, is among the finest in Europe and deserves at the very least a full morning to explore properly: its famous contrade (city districts) are genuinely active and the city has an energy all of its own.
I have a full guide to Siena here, also with lunch recommendations!
Explore Cortona
About 40-45 minutes from Montepulciano, Cortona is one of the most beautiful hilltop towns in the region and a wonderful day trip option for those based in the Montepulciano area.
The town has the lovely medieval layout and feel you expect from an ancient Tuscan hamlet but also has extraordinary Etruscan museum which makes it stand out from many of its neighbors.
It is well worth the drive and the countryside here looks slightly different from Val d’Orcia, so it is worth the drive! I have a guide on to how to take a day trip to Cortona here.
Take a scenic drive
The area around Montepulciano contains some of the most beautiful roads in Italy, and one of the most pleasurable things you can do here is simply drive them!
The SP146 between Pienza and San Quirico d’Orcia is the iconic one: the cypress-lined strade bianche (unpaved roads – don’t worry, super easy to drive them with a normal car, we did is with a 15 year old one!) leading to Monticchiello are beautiful, the drive from San Quirico with the views of Vitaleta Chapel a delight and the he approach to Bagno Vignoni stunning.
My advice: take at least one afternoon with no museum, no agenda, and no destination more specific than “the Val d’Orcia drive.” Stop in any town, get a board of meats and cheese as a snack, sit outside and watch life pass by. The ‘best thing to do of all’!
For families: the best experiences in Montepulciano with kids
The Montepulciano area is genuinely wonderful for families, but expectations need to be accurate: this is very much a place to slow down and take life slow, as far from a theme park feel as it gets, so some planning and picking the right seasons is a must!
Our favorite time to be here is the early / late summer, when the kids can make the most of the outdoor pools during the hottest hours of the day and sightseeing is done as aperitivo hour.
Lovely experiences kids will also enjoy are:
Farmhouse lunch in Agriturismo via della Stella, a lovely way to stay outside for the day and enjoy the countryside
Cooking class in Locanda Demetra (country setting) or in a local trattoria in town, perfect to take a break while sightseeing Montepulciano town. A fun, hands on activity and a lovely, different way to have lunch.
Podere Il Casale — a nice farm with sheep, goats, cats, and a nice restaurant for a lunch with a view.
The thermal springs at Bagni San Filippo — a natural adventure in the forest, where you find hot brook! Free, magical and completely unlike anything else. Children who love the outdoors will be enchanted.
The fortress garden in Montepulciano — our kids loved it; lovely for a break with benches, shade and views. Simple but very welcome after the steep climb up across the town!
The Gladiator Cypresses in Pienza — older children who have seen the Gladiators will enjoy the sort walk to the famous Gladiator Cypresses and can have fun replicating the scene!
Where to eat in Montepulciano and surrounding area
The food of this area is deeply Tuscan: honest, seasonal, earthy and completely delicious. Pici pasta (thick, hand-rolled spaghetti), wild boar ragù, local Chianina beef, pecorino in all its forms, and of course Vino Nobile at every meal.
We had amazing meals everywhere so it really is hard to go wrong here, but some special addresses you may want to check if you are after something special are:
La Lupaia https://www.lupaia.com/en/dining/
Tistorante Indigeno – https://guide.michelin.com/ie/en/toscana/montepulciano/restaurant/indigeno
Podere il Casale https://podereilcasale.com/en/
Il conte Matto https://www.contematto.it/en/
Trattoria Toscana https://www.palazzodelcapitano.com/antica-trattoria-toscana-al-vecchio-forno
How to get around
The Montepulciano area is best explored by car: there is really no other practical way to reach the Val d’Orcia villages, the thermal springs and the wine estates and since the driving routes are scenic themselves, driving here is also an activity, not just a way to go from A to B.
Driving here is rather simple. The country roads are well kept and not busy and while some are winding, they pose no special challenge.
The one moment when overseas visitors may find less familiar is entering the towns: since they are on hilltops, the roads up are often winding and narrower than in the US and may feel cramped of not used to them. I am making a comparison specifically with the US as it is American visitors often remarking about them: if you come from Ireland for instance, you will have a different perception 🙂
Despite this, going slowly is all it takes to tackle them: if you can avoid massively oversized cars, this will also go a long way to help you here if you are not used to Italian country roads.
As with all Tuscan hilltop towns, the centre of Montepulciano is a ZTL (limited traffic zone) — follow the P signs for parking outside the walls and explore on foot. Parking is pay and display; bring coins.
Find here >> my tips for driving in Tuscany | And here >> my guide to parking in Italy
I hope this guide helps you plan a wonderful stay in Montepulciano and surrounding area. It is one of the most beautiful corners of Italy and one I never tire of coming back to. Safe travels!
