Montepulciano is a breathtaking small town with a gorgeous Tuscan rhythm. Set atop a hill in the province of Siena, the far-reaching views of the rolling Tuscan hills can be enjoyed from just about every part of town. On one side of town is the Val d’Orcia, on the other you will find the Val di Chiana, and you will be in the heart of Tuscany.
I tend to linger in Montepulciano for days (or weeks!) to soak up and live that slow Tuscan vibe, but you could easily get a great feel for the town in 1-2 days. Below is a relaxed, vetted, economical, comprehensive, and very Tuscan 1-day itinerary to consider if you have limited time. But prepare yourself – you’ll want to come back and linger too.
Early Morning – Bar Delle Erbe
Head to Bar delle Erbe, in Piazza delle Erbe. This cute and friendly bar and coffee shop smack in the middle of everything, usually packed with locals and some students from the local Italian language school. Silvia and Alessandro, the proprietors, are always in here and Alessandro will likely be the one making your coffee. They will let you sit inside or outside for no additional charge (usually there is, for sitting at the bar instead of standing in Italy). The coffee is excellent, and their pastries are known for being of very good quality. Go early and beat the crowds.
Morning – Walk to San Biagio
Take a leisurely walk down to the Sanctuary of the Madonna di San Biagio. This striking church constructed in the late-renaissance is equally beautiful on the outside as it is on the inside. If, from the bar Delle Erbe, you make your way around to the Val d’Orcia side of the town on via Piana (easy 5 min walk), you can continue on via dei Grassi and head straight down the street on foot which takes you right to the church. It is a lovely walk as you continue just outside of the old gates of Montepulciano through the Tuscan country side and only takes ~10-15 min to arrive at the church by foot. It opens for visitors at 10:00am most days. Enjoy the nature, then cool off inside, feel the history.
Early Afternoon – Hang out in the Piazza Grande
Head back up to town and make your way to the Piazza Grande, you will already be on the correct side of town if you head back up from San Biagio. The Piazza Grande is the main focal point and historical meeting place of the town.
You will find the main church, Santa Maria Assunta, as well as the Palazzo Comunale serving as the town hall including with its famous clock tower. Hang out here and soak in some Tuscan sun with locals and visitors alike. Most days there are kids playing soccer or running around the piazza, their parents on the sidelines chatting or sometimes seated at one of the tables that line the piazza having a cold drink. You can have a cold drink yourself and watch the local town life in action.
Afternoon and lunch – Wine tasting & Lunch at the Enoliteca:
From the Piazza Grande, if you continue up Via di S. Donato which leads out from the piazza immediately from the left of the Palazzo Comunale (if you are looking straight at it) and pass its lovely shops you will make your way slowly and easily up to the highest point of the town, The Fortezza. The Fortezza is stunningly beautiful with manicured gardens, large trees providing lovely shaded walkways lined with benches, a community playground and garden, and epic views. Every time I am up here there are beautiful cool breezes that put you at ease with the tranquil landscape around you, you will feel relaxed instantly. But the best part is that the Fortezza houses the Consorzio del Vino Nobile di Montepulciano, a consortium which protects and promotes the image of Vino Nobile di Montepulciano, Montepulciano’s signature DOCG wine.
The Consorzio provides and staffs the Enoliteca (tasting room) built entirely on top of Etruscan ruins which are visible through the glass floor as you walk through, where you can taste every single producer of Nobile wine. Check in at the front desk with the wonderfully gracious staff who all speak English and get a wine card (don’t lose it!), after which you will be led behind to the tasting room of the Enoliteca and can sit, wander, and taste at your leisure. It is casual – you grab a clean glass, walk up to the machines, insert your card and push the button for either a small taste or a full glass of any wine you want. If you would like assistance, the very knowledgeable staff will answer any question you have and will even hang out with you and chat if it’s not busy, or they can provide you with a guide book covering all of the producers and wine characteristics so that you can read and chat.
There is a lovely outdoor space, complete with furniture, a garden, and the most amazing views of the valley. When I come here I can never decide whether to sit outside or in, both are very comfortable and relaxed, so I usually do both. When I was learning Italian I used to come here in the afternoons after my classes and do my homework outside with a glass. I like to eat lunch here via their selection of meat and cheese boards which they will prepare by hand for you upon request to accompany your tasting. After you find a producer you like, push the button to pour yourself a glass and head outside for the view and to relax in the Tuscan breeze. You won’t want to leave.
Late Afternoon – Elegant coffee at Caffe Poliziano
Now that you are nice and relaxed, head back down from the Fortezza and Enoliteca back to the Piazza delle Erbe, where just a few steps up the Via del Corso (one of Montepulciano’s main streets) you will find the famous Caffe Poliziano. A step up from a normal bar, the elegant Caffe Poliziano is a little more upscale and has a very important and interesting history. Even though it is a more upscale experience here, the baristas and staff are all very nice and welcoming. Grab a caffè or a macchiato (no cappuccino – as by now it will surely be after 11:00am) and one of their delicious sweet pastries. I like anything they make with pistachio, but you’ll see there are many delicious things to choose from. Tell them ahead of time if you plan to sit down, rather than seating yourself, and they will guide you to a table. If you can, get one in the back as you will be privy to another breathtaking view of the entire Val di Chiana. You can get the pastries to go too!
Early Evening – Aperitivo at E Lucevan Le Stelle:
Without a doubt my most favorite thing in Montepulciano…maybe even in Italy. Aperitivo with an indescribable view as the sun sets over the Val d’Orcia. To experience this is a game changer, and if you want the best drinks, the best view, the best staff you must head to e Lucevan le Stelle.
Lucevan, as I call it, is a true wine bar and I love it. It is casual and comfortable, perched high up in the Piazza San Francesco. They have their own hotel/lodging here as well where you can stay. I come here nearly every single day to fare l’aperitivo (do the aperitivo). You’ll want to grab a spot on the outdoor deck facing the incredible view and order your spritz or drink of choice. The camerieri (servers) here are quite nice, speak English, and are very knowledgeable about wine. Ask them, they will help you.
Sip your spritz, for me that would be a Campari spritz, and watch all of the happenings in the small piazza – tourists and locals coming up to enjoy the view and take millions of photos – justifiably so, cars zooming in and out parking where they shouldn’t, nuns in groups going into and coming out of that little door in the corner of the piazza that leads into the church cloister (I always want to sneak in there!), locals shouting Italian greetings to each other across the piazza. Watch the sunset and soak it in, this is another locale in Montepulciano that will call you back again and again. If you are a night owl come back here after dinner for a nightcap. They are open late.
Evening – Dinner at Rosso Rubino Trattoria
After your sunset cocktail, because dinner in Italy starts at the earliest 7:30pm, head from Lucevan back to the familiar-by-now Via del Corso and make your way to Rosso Rubino Trattoria.
This family run trattoria is the best restaurant in Montepulciano in my opinion. The food, the ambiance, the proprietors can not be matched by any other restaurant in town. There are only 7-8 tables and it is very comfortable inside. It is owned and run by Vittorio and Cristiana. They showcase the best of local, thoughtful, hand prepared Tuscan cuisine from the region. Everything is made from scratch. Vittorio and Cristiana are both here every night – Cristiana helping to seat you and also taking care of your at your table, Vittorio cooking in the back but coming out constantly to check on things and to be sure you have everything you need. He likes to chat so if you see him don’t be afraid to strike up conversation, sometimes he will even bring to your table the truffles and porcini mushrooms he will be using to prepare your pasta.
Order the pici (pasta), a specialty in the province of Siena and a must if you are in the region. And if you ever see his “pici con crema di ceci e guanciale di cinta” written on the chalkboard menu of the day – order it without hesitation, it is one of the best plates of pasta I have ever had in Italy. Last year I asked him for it because it was not on the menu and he told me “Come back tomorrow I will make it for you” and the next day it was on the menu and sold out, it’s incredible. Let Vittorio help you pick the wine – he curates his own list from local producers and will know which to pair with your meal, my favorites are anything from Podere della Bruciata. And get dessert – they are all hand made. Be sure to call ahead to reserve +39 0578 716373, there is no website you can’t reserve online. Buon appetito!
Late Evening – Stroll back to the Piazza Grande
Fare una passeggiata (take a stroll) back over to the Piazza Grande and experience the piazza at night. It is glowy and magical, and very safe. It is also nice to take a walk after dinner here, most people do it, and you can experience the town from a different perspective.
How To Get To Montepulciano
Montepulciano is close to the autostrada and the train station at Chiusi-Chianciano, so it is very easy to reach Montepulciano both by car and by train.
If you are coming by car, from the Rome airports take the G.R.A. (Grande Raccordo Anulare) and then enter the A1 motorway towards Florence, exiting at Chiusi/Chianciano Terme. Then follow the signs for Montepulciano. If you are coming from the Florence airport, enter the motorway at Firenze Nord, towards Rome, and exit at Valdichiana/Bettolle. If you are arriving from Pisa, take the “Fi-Pi-Li” (Florence – Pisa – Livorno main road), then enter the A1 motorway in the direction of Rome. Exit at Valdichiana/Bettolle. Then follow the directions for Montepulciano.
When you arrive, leave your car in one of the parking lots outside the city, as the historic center and main part of the town is closed to traffic and unless you live here you are not allowed to drive within the city walls (huge fine if you do). You cannot enter with your car.
If you arrive by plane, you can fly into Rome Fiumicino – Leonardo da Vinci airport, Florence Amerigo Vespucci airport or Pisa Galileo Galilei airport.
If you’re coming by train, no matter where you are coming from get off at the Chiusi/Chianciano Terme station (not Montepulciano Stazione station). At the Chiusi/Chianciano train station you can find both bus and taxi. If you take the bus from Chiusi to Montepulciano, get off at the bus station. From there you can come into the centre on foot or take the little white bus (“Pollicino”). If you take the Pollicino, get off at Piazza Michelozzo. Please notice that on Sundays there are only a few buses from Chiusi to Montepulciano.
You can find all information about the Italian bus schedules if you download the app “at bus Autolinee Toscane”.
Or you can do what I do every time I come to Montepulciano and just call Andrea Ceccarelli (+39 348 7335343). He is a personal driver with years of experience, speaks English, and is one of the nicest people I have ever met. If you call him and arrange ahead, he will come pick you up from anywhere in Tuscany or even Rome and drive you straight into the city (his car can go there). The cost from the Chiusi-Chianciano train station is around 60 Euro, and he charges ~350 Euro to be picked up at the Rome Fiumicino Airport – at times worth it after a long flight. Andrea is a kind, honest, and gentle person and you won’t regret calling him. He is very responsive on WhatsApp.
Montepulciano is a place I love dearly and I will always come back. If you want any more information, recommendations, or just to chat you can contact me here. Enjoy this fantastic town and no doubt you will always come back too! ~Amy
