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Visiting Montepulciano, Tuscany

The medieval and Renaissance hill town of Montepulciano is one of the most striking and picturesque villages you can visit in Tuscany. It’s location, high up on a limestone ridge, gives you breathtaking 360 degree views of the surrounding Tuscan countryside. The valleys and hills lined with olive groves and vineyards, and dotted with cypress trees and ancient farm houses are some of the most spectacular you can witness. Montepulciano also quite possibly has the most perfect golden hour I have ever seen! All this, along with it’s fabulous wine, food and shopping, make Montepulciano a must on your Tuscany travel list!

Montepulciano is a small town which makes it quite easy to walk to all the main sites. I think it makes it a nice place to travel and take a break with a young family too because you are never very far from your hotel or Airbnb….plus it has playgrounds :) (see below). You could easily visit here in a day, but I think it is worth spending the night because it is such a lovely city at sunrise and sunset. If you aren’t able to spend the night just make sure to get here early for a coffee (and a view) at Caffe Poliziano and stay past sunset so that you can take in one of the the most magnificent golden hours in Tuscany!


What to see and experience in Montepulciano, Italy


  1. Taking in the views of Montepulciano & where to find them

You are in for a treat here if you love wide open high views of some of the most beautiful landscape in the world. Here are some of my favorite places to take them in!

  1. The panoramic view point at Vicolo della Mura at Vicolo dei Cacciatori, 1

  2. Caffe Poliziano balcony (also the best place for your morning cappuccino!!) at Via di Voltaia Nel Corso, 27/29

  3. The Gardens at Fortezza Medicea at Via Fiorenzuola Vecchia, 10

  4. Via Ricci View - Via Ricci, 23

  5. Valdichiano View Point at Vicolo del Leone, 3

  6. De’ Ricci Cantina View at Via Ricci, 11

  7. The benches along Via del Poliziano in front of the Chiesa di Santa Maria dei Servi

  8. A pretty walk with a view along Via delle Spiaggie


2. Endulging in some fabulous Eating and drinking in Montepulciano

Montepulciano is not short of mouthwatering food and drink, in fact, it is home to one of the most well known Italian wines, Vino Nobile di Montepulciano. This red wine has DOCG status and is made primarily from the Sangiovese grape varietal. You will find it in every restaurant in town as well as some of the incredible wine cantinas around town, which is another thing…these cantinas are not like any you have ever visited before and not to be missed!

Some of the most well known ones are…

  1. Cantina Contucci

  2. Cantina De’Ricci - I think this one may have the most impressive cantina!!

  3. Cantina Talosa

    All of the above offer wine tastings as well as tours of their cellars. If you don’t have time to take a tour, simply walk around and take it all in for yourself. Either way, these are something not to be missed! Check their websites in case you need to reserve a tour ahead of time.

If you are looking to dine in Montepulciano you will be happy to know that there is an abundance of fabulous restaurants here! This part of Tuscany is known for it’s cucina povera….the simple rustic “poor cooking” that dishes out some of the most beloved recipes in all of Italy. Try Panzanella (tomato & bread salad) in the summer time or Ribollita (vegetable soup) in the colder months. In the mood for something a little heartier? Try some handmade pici pasta or cinghiale (wild boar). Make sure not to miss sampling some of this areas cheeses too. This part of Tuscany is know for it’s delicious variety of Pecorino cheeses (my favorite!!). Also, don’t miss my favorite place for breakfast or aperitivo - Caffe Poliziano :)


3. Exploring Montepulciano’s Piazza Grande

Piazza Grande sits at the top of Montepulciano and it is the perfect place to sit on the church steps with a panino and watch the world go by! It is surrounded by breathtaking palazzos, including Palazzo Comunale and Palazzo Contucci, and the Cathedral Saint Mary Of The Assumption. Overall this is a quiet and peaceful piazza so it feels wonderful for a family or if you just need some peace. We felt like the kids could walk up and down the steps and move around a bit without getting in the way. You may feel a bit like your walking around in Piazza della Signoria thanks to Cosimo De Medici who ordered the design on The Palazzo Comunale to look like the famous Palazzo Vecchio in Florence. Make sure to take in the ancient feel of the Duomo’s unfinished façade before stepping into it’s elegant interior. And before you leave, head on over to Pozzo dei Grifi e dei Leoni, the old well opposite the church to make a wish (to come back to Italy of course!).


4. Walking the Corso & SHopping in Montepulciano

Montepulciano is the perfect place to meander while enjoying some fabulous shopping and taking in the sites of the lovely historic center. Via di Gracciano nel Corso at the lower part of Montepulciano is lined with shops selling items such as artisanal food and wine, clothing, bags and purses made from that fabulous Tuscan leather, handmade ceramics, art and souvenirs. This is definitely a town where you could find something for everyone on your gift list! Make sure to take the time to check them out.

The main Corso in Montepulciano does have a fairly steep incline so depending on which way you are going you may be in for a bit of a hike. If you plan it right though this isn’t too much of a problem. I suggest starting at the bottom of the hill and doing your shopping and sightseeing while slowly making your way up to the top. This way you can take lots of lovely little pauses along the way.

Start at Via di Gracciano nel Corso which starts at Porta al Prato. This will take you past the above as well as the Chiesa di Sant'Agostino and the Torre di Pulcinella (make sure to look up and see the Pulcinella - the masked Joker statue standing on top of the clock tower). When the road ends (there will be a really beautiful bank in front of you) take a left onto Via di Voltaia Nel Corso. This will take you right by Caffe Poliziano…the perfect place to stop for a caffe or a aperitivo and take the the most breathtaking view! After this you can keep heading up the hill towards Piazza Grande. There are still some shops at this point but not as many as the lower part of the road. When you come to the small piazza with Sax Wine Bar on your right, switch back past some purse shops (still regretting not buying something in one of these!) and keep heading up (yes, more up!) to Piazza Grande. You will walk right by the Contucci Winery as you turn left into Piazza Grande.


Traveling with Kids to Montepulciano

This is a wonderful town for kids! There are great views, friendly people, a big piazza to run around in and TWO parks with playgrounds!! This is something that Italy lacks in comparison to the US so it is very exciting for the little ones when you find one. There is the Fortezza Playground located at the top of the hill at Via Fiorenzuola Vecchia, 10 and the playground at the Giardino di Poggiofanti located at the bottom of the hill (right outside the Porta al Prato) at Viale I Maggio. Both playgrounds have gardens to walk around. The playground and gardens at the Giardino di Poggiofanti are bigger while the Fortezza gardens have a lovelier view. Both are wonderful though and both will leave the little ones with LESS energy ;)

The first 4 pictures below are of the park at the bottom of Montepulciano and the second 4 are of the park at the top of the hill.

Getting to Montepulciano

Montepulciano is just off the A1 highway in the province of Siena in Southern Tuscany. By car it is 75 miles southeast of Florence, 115 miles north of Rome, 8 miles east of Pienza and 43 miles southeast of Siena. Montepulciano is well connected and is easy to reach by bus or train. If you take the train you will need to take an additional bus to reach the city itself because the station is in the valley. The ride is approx 30 min from the station by bus.

Buon Viaggio!!