Our guide to planning your day in Montepulciano

We love Montepulciano and think it’s a great homebase when you’re looking to visit different towns in this area of Tuscany. We talk about things to consider when choosing a place to stay here. This is a guide to give you some ideas for planning your day in town.

A couple things before we get into it –

While Montepulciano is known for their Nobile di Montepulciano, we are not serious wine drinkers. Yes, we enjoy a glass of wine, even taking part in winery tours and tastings, but it’s not our main focus for visiting the area. In a lot of ways, we just love being in Tuscany. The people, the food, shopping in locally owned stores, architecture, gorgeous landscapes – that is why we keep coming back. So this will not be a comprehensive list of wineries in the area. If you have only one day in Montepulciano, here are some suggestions on how to make the most of that day.

Getting there and around town –

We talk extensively about getting to and around Montepulciano here. So for more information on renting a car, hiring a driver or taxi, check out that post. No matter how you get to town, you will most likely start at the Porta al Prato, the main gateway to the historic part of the city. Everything is literally uphill from there. Much of Montepulciano is almost a kind of loop. Of course there are side streets and off shoots, but in the end, it’s pretty easy to navigate. So as you head into town, you can feel pretty comfortable that you will not get lost.

Walking is really the way to go to. This is how you will enjoy and get a feel for the vibe of town. It’s good to try to plan out your day, seeing things as you ascend to the top. We know that’s not always possible, but with a little planning you shouldn’t have too much back and forth in town.
Another option for getting an overview of town is taking the little red bus – Montepulciano City Tour. It’s a cute, small red electric bus that takes a 30 minute tour of the city, including Tempio di San Biagio, for €10 (as of fall ’24). It also includes an audio tour. There are 3 stations in town and you buy tickets on board, so you can walk for a bit and decide to take the tour for a little break later in the day.

What to see –

Piazza Grande (at the top of town) – If you’re a fan of The Twilight Saga: New Moon or the Medici series, you will recognize the Piazza. If you’re up for a climb, you can go up the tower of the Palazzo Comunale (Townhall). We have not personally climbed to the top, it’s just not our thing. But if you’re looking for a panoramic view of the city, it is something to consider. We loved sitting on the side of the piazza and just taking it all in. One evening, waiting for dinner, we sat and watched a group of kids playing fútbol in the square. Backpacks as goal markers – running, laughing, and having a great time. It was a great way to feel we were a part of town, not just visiting.

Fortezza Medicea (about a 5 min walk from Piazza Grande) – Inside is now an enoliteca (wine shop & tasting room), but the real reason to come here is to walk through the gardens and take in the views. They are truly stunning, and you can take in so much of the countryside. In the shop you will find glass floors that show the Etruscan ruins found under the fortress, so it might be worth a quick walk through. However, for wine tasting, you will have better options elsewhere.

Fattoria della Talosa (Via Talosa 8, just minutes from Piazza Grande) – If you’re looking for a wine tasting in town with a bit of history, this is a great stop. They have cellars located in the basement of two of the oldest buildings in Montepulciano. They offer many options for tastings & tours. You can choose to make it a short break in your afternoon or plan a tour that also includes lunch. They have a wide range of options to fit how much wine and food you’re interested in. It’s a good plan reserve it ahead of time to make sure you have a spot!

Where to eat –

Breakfast – Palazzo Avignonesi Caffetteria (Via Gracciano nel Corso, 89, minutes from Porta al Prato) Since many hotels offer breakfast, that’s always a great option. But if you want to get going and get into town to make the most of your time, this is a great option. It’s a beautiful location with delicious espresso (of course) and pastries from Pasticceria Regina – their pastry shop outside of town. If the weather is nice, sit outside and watch the town come to life.
Lunch – Il Teatro (Piazzetta del Teatro, 5, minutes from Piazza Grande) – After you’ve made it almost to the top of town, this is the perfect place to have lunch. The owner, Salvatore, Chef Andrea, and the entire staff are amazing – so friendly and helpful. They have traditional dishes and some things you might not expect, but all fabulous. Another great thing about their restaurant is it’s one of the few that is open all day, so you don’t have to worry as much about your timing. However, it’s very small, so if you’re sure you want to try it – try to make a reservation. They have delicious antipasti, so if you don’t want to fill up, it can be a lighter lunch to save room for some gelato.

Dinner – Osteria Porta di Bacco (Via di Gracciano nel Corso 94, steps away from Porta al Prato) Yes, this make perfect sense because it is on your way out of town, but it’s also an amazing restaurant, one of our favorite restaurants in Montepulciano! The food is traditional Tuscan cuisine, made perfectly. The staff is so welcoming and the restaurant is beautiful. And of course, an amazing wine list. Sitting inside is great, but outside is a wonderful place to watch the world go by while you have a delicious meal. The owner, Andrea Sorlini Bifolchi, a Montepulciano native, also owns Palazzo Avignonese, as well as a couple other restaurants in town. We talk about his other locations here, but if you have only one night in town, don’t miss this one!
Gelato – Buon Gusto Gelateria (Via di Gracciano nel Corso 50) This is a little closer to Porta al Prato than to Piazza Grande, so it might require some effort to make it fit into your day, but you want to get gelato here before you leave town! The owner, Nicola, has an intense commitment to natural and seasonal flavors. You will also find some unique combinations that are all worth a try. And if you’re looking for just amazing chocolate gelato, he has one of the best we have tried – in the world. Yes, a bold statement, but feel confident in saying that. Stop in early in the day or after dinner, just make sure you stop in.

Where to shop –

Shopping during vacation can be a very personal thing. If you have gifts to buy for family back home, kids or grandkids to get souvenirs for, or maybe you’re just looking for yourself. What you’re looking for will determine what shops are best for you. For us, this list has more to do with the quality of what we found in the shop, balanced with the prices. How welcoming the staff, usually the owners, were when we walked in, and how unique the items they offered were. Here are a few we make sure to stop in each time we visit.

Opio/Sette (Via dell’Opio nel Corso 7) – clothes & accessories
HMFS (Via del Teatro 18) – unique shoes & purses
Manu Factum 1868 (Via di Voltaia nel Corso 102) – classic handmade Italian ceramics
Cogli l’Attimo (Via di Gracciano nel Corso 12/14) – clothes & accessories
Gessica La Pira (Via dell’Opio nel Corso 12) – one of a kind artwork

Do you have more than one day planned for Montepulciano? Here are a few more of our favorites that are within about 30 minutes of town.

If you’re looking for the classic Tuscany winery experience, you can’t go wrong with Avignonese. They are an organic and biodynamic vineyard with a deep commitment to the land they grown on. They offer everything from simple wine tastings in their wine bar to a full tour, lunch, and wine pairing experience. (About 25 minutes from town, Via Colonica, 1)
For more beautiful views and care of the land, La Foce is another great stop. They offer tours of their stunning gardens on select days of the week. They also have a restaurant just across the street as an option for lunch when visiting. (About 20 minutes from town, Strada della Vittoria, 61, Chianciano Terme)
If it’s a Michelin Star experience you’re looking for, plan dinner at Osmosi, They have a range of incredible tasting menus, from 5 to 9 courses. No matter what you choose, plan for a full evening of creative and delicious food. (About 15 minutes from town, Via Umbria, 65)
Maybe all of these sound a little too fancy, then head over to Fattoria Madonna della Querce. You can walk among the olive trees and meet their fabulous Cinta Senese pigs. They offer farm tours and tastings, as well as 4-wheeler tours of the Val d’Orcia. Not matter what you pick, it’s a great way to really get to know the Tuscan countryside. Also, the owner Roberto might be one of the kindest people you will meet. (About 10 minutes from town, Via Madonna della Querce 6)