Truth be told, in the small hill towns of Tuscany, you will be safe going into almost any restaurant. (We mean very small – once you get to Siena, Pisa, Florence, this doesn’t necessarily apply) You’re not going to find the super touristy places that make what they think tourists will eat. Usually they have a sad, high volume/low quality versions of Italian food. They are getting people in with ease of ordering – menus in English, pre-fixe menus so you don’t really have many choices, etc. It’s not how much the meal costs. Really, you will find a lot of great local restaurants that are not very expensive. They are using local ingredients and they have small menus, so that helps them keep prices reasonable. However, it’s possible no one in the restaurant will speak English and the menus will not be in English. Of course, this is not always the case, but they certainly will not have large signs out front in English. But it will be worth getting out your Google Translate to make it happen. As always, a smile, Grazie & Per Favore go a long way. We’re getting a little off topic…
There is a range in the restaurants we love, from homey & comforting to an incredible Michelin Star restaurant. A few things are common

to all of them – delicious local & seasonal ingredients, tremendous care and dedication to serving great food, and good service. Most are in Montepulciano, but few are in neighboring towns. Let’s go through them.
Montepulciano –
The first few are all within a couple hundred feet of the Porta al Prato, the entrance to the lower part of town. How are there so many amazing restaurants in such a small area? They are all run by Montepulciano native, Andrea Sorlini Bifolchi. His commitment to quality, local food & wine, and the town itself, is evident in each location. There is a range on atmosphere and food in each of them, so it’s possible to visit all of them during your visit and have a different experience every time. However, what is consistent with all of them is a warm and welcoming environment, great staff, and delicious food & wine. All are located on Via di Gracciano nel Corso.
- Porta di Bacco Just as you enter into town, you are greeted by this location. It is also one of the first restaurants we ate at in Montepulciano and we were in love from the beginning. The offer traditional Tuscan cuisine in a casual, yet elegant setting. If you can, sit outside, order a bottle of wine, and just watch the world go by. It’s fabulous!
- La Bottega del Nobile A few more steps into town, it’s the most elegant and refined of this group of restaurants. While it still uses the wonderful local ingredients, there is a level of artistry here that is different than the others.
- Trattoria Il Marzocco Continuing into town, this is the most casual of the full service locations. But don’t let that fool you! The food is amazing. It proves that will great ingredients, even a simple dish can be outstanding.
- Palazzo Avignonesi Caffetteria This is just across from Trattoria Il Marzocco. A perfect coffee shop for anytime of day. You can start here before you get going. Or as we did, it’s great to take a break in the afternoon. From a espresso to a Negorni or a pastry to a pannino, they have you covered.



- Il Teatro (Piazzetta del Teatro, a 2 minute walk from Piazza Grande) This is the meeting of traditional local recipes with a bit of a personal approach. Owners Andrea & Salvatore are there to make sure you have an incredible experience. Chef Andrea is in the back of the house making sure your food is delicious and Salvatore is front of the house, ready to answer questions and suggest the perfect wine to pair with your meal. As with many restaurants in the area, Il Teatro is TINY. Seating for about 20 or so inside and just about 6 outside.
- Osteria del Borgo (Via Ricci, just steps away from Piazza Grande) Traditional Tuscan dishes and one of the best views for watching the sunset over the Tuscan Hills. The wonderful thing about Osteria del Borgo is that it’s like being in someone’s home. It is Tuscan comfort food at its best. But don’t let that fool you, it also has one of the best, most extensive wine lists you will find and in Tuscany, that’s saying something. If you can sit on the terrace, it will be even better.
- Osmosi (Via Umbria, about 10 minutes outside of town) From the first time we tried Osmosi, we knew it was a Michelin Star restaurant. Everything about it – the simple elegance, their innovative menu and attention to detail in everything they do. What is wonderful is they use innovation to bring out the best flavor in food not just for the sake of being different. If that wasn’t enough, one of the best things about Osmosi is the owners, Simone & Elena, Chef Mirko, and the entire staff. Sometimes with this level of cuisine, there is an uncomfortable vibe in a restaurant. There is not the case at all here. We were so pleasantly surprised at how warm and welcoming everyone was.



Pienza –
- Buon Gusto Gelateria (Via delle Case Nuove, a 3 minute walk from Piazza Pio II) When we try a gelateria for the first time we get at least one chocolate and one pistachio – they are our control flavors 😊 They did not disappoint. Wonderful, seasonal ingredients (Luckily chocolate is always in season), all made in house. If you’re looking for something a little different, they have that too – Strawberry & Rosemary, Lemon & Basil, Peach & Lavender. No matter what you have a taste for, stop in. They have a location in Montepulciano as well on Via di Gracciano Nel Corso.
- Townhouse Caffe (Corso il Rosselino, also a 3 minute walk from Piazza Pio II) Not your typical Tuscan restaurant, but it takes local ingredients and adds in flavors you might not expect. It’s a great, laidback environment with delicious food. Also, if you’re craving an American classic during your travels, they have amazing burgers! If the weather is nice, and it’s available, sit outside in the walled garden.


Going a bit into Umbria….Castiglione del Lago & Cortona –
- L’Angolo del Buon Gustiao (Via Vittorio Emanuele, a 5 minute walk from Palazzo della Corgna in Castiglione del Lago) Small and lively, this is a perfect lunch spot if you’re visiting for the day. They have many great options for sharing – plates of cheeses, cured meats, and crostini with wonderful toppings.
- Taverna Pane e Vino (Cortona – Just steps from Piazza Signorelli) This casual and cozy restaurant is tucked in the cellars of a 14th century building. The menu is full of simple, traditional, and delicious dishes. You will come across dishes you might not find in other restaurants such as Bruschetta con Fagioli e Aringa affumicata (beans & smoked herring) or Pici alle Molliche (breadcrumbs, anchovies, & chilies). The staff is wonderful and helpful, so ask questions and try something you’ve never had before!
- Snoopy Gelatateria (Cortona – Right in Piazza Signorelli and steps away from Piazza della Repubblica) Another great gelato option. Their chocolate and pistachio passed the test as well. They also have a wide range of flavors. We had ricotta and figs our last visit and it was amazing. They have just a few seats outside, but if you take your gelato and walk to Piazza della Repubblica, you can sit on the steps and watch the world go by.


General tips for dinning in the area –
- Restaurants are small and can fill up fast. Research before you leave and try to make reservations in advance. Some are on The Fork (Europe’s version OpenTable), some are on OpenTable, and some you will need to email or call. If you are traveling in the busy season (May to October) you will want to have reservations, otherwise your options will be limited. Don’t speak Italian? No worries! Google translate gets the job done for reservations done through email.
- You will notice menus have Antipasto, Primo, Secondo, and Dolce courses. Just like in the US, you don’t have to order from each section. Although portions will be a little smaller than ours, so that allows for trying a couple of items and it is very common to order from at lest two of the sections.
- This may seem random, but you will see a lot of steak tartare on menus. As in, most restaurants. That is because the Chianina beef is a prized ingredient of the area. It is some of the best, highest quality beef you will try. If you love steak tartare like we do, definitely order it. (L’Angolo del Buon Gustiao has some amazing options) If you have ever wanted to try it, this is the place to do it.
- If you’re not sure where to eat and you’re checking options on TripAdvisor, make sure to look at the reviews in Italian as well. Google Translate will help you out again (the option to translate right on the page). This will give you a better sense of what locals think.