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Striped front facade of church in Montepulciano, Italy. You can see the belltower at back of church.

One Day Itinerary for Montepulciano – 24 Hours In Tuscan Wine Country

Last updated on February 22nd, 2024

Are you planning a day trip to Montepulciano and need some advice on how to maximize your time?

Maybe you need help deciding which things to do in Montepulciano on your short visit.

I have been living here for 10 years and know my way around the Montepulciano block. I have done everything there is to do – and then some – and I have made many day trips to Montepulciano with my friends and family.

After years of these mini trips, I am confident in sharing my one day itinerary in Montepulciano for any type of visitor, be it a family or a newlywed couple.

So put down those guide books, stop the research and look no further. In this guide, I will share with you exactly how to spend 24 hours in Montepulciano, including what to do and where to eat. And I’ll scatter in some helpful tips for your visit.

Note: This one day itinerary may seem like it’s jam-packed but many of the top things to do in Montepulciano can be accomplished in a short amount of time and Montepulciano is a small town.

One Day Itinerary for Montepulciano – An Overview

Time Of DayActivityGood To Know
8:00-10:30 amWalk From Port al Prato to midtown, stopping at Città Sotterranea di Ercolani for a wine tour. Start anytime before 10. Alternative Trolly ride for families or people who prefer not to walk and skip wine cellar tour (see wine cellar later at Cantina Contucci)
10:30/11:00 amCoffee at Bar PolizianoMenu includes traditional Italian breakfast and international/American classics
12:00 amTour Montepulciano up to Medici Fortezza and back to Piazza GrandeStop to visit the other historic wine cellars on the way to buy other wines
1:00-3:00 pmLunchChoose From: Osteria del Conte, Il Teatro or Acquacheta 
3:00 pmWine Tasting at ContucciChoose either a free tasting at the cellar or a more curated experience at their Enoteca in Palazzo Contucci, one of my favorite wine bars in Montepulciano
4:00 pmPanoramic views (with or without clock tower climb)Climb clock tower, weather permitting
5:00 pmHop on Trolly tour in Piazza Grande to visit Temple of San BiagioHop on and off at four different stops
6:00/6:30 pmAperitivo at Bar Gelateria DuomoOrder a Spritz or other non-alcoholic Italian beverage
8:00 pmDinnerChoose From: Trattoria di Cagnano or Pentolaccia
10:00 pmWalk to base of MontepulcianoWalk back down to base of Montepulciano & stop for gelato
Huge stone wall with large archway in Italian village.

The Morning In Montepulciano

Start your morning at the base of Montepulciano and make your way up slowly but surely to the top. Along the way, you will come across various souvenir shops, cheese shops, wine cellars and shops and churches that you may wish to peep into. 

If for any reason walking is not an option, opt for the trolly ride up to the top. This will, however, prevent you from stopping in or window shopping as the trolly ride only has four designated stops. 

Entrance to Cantina Ercolani in Montepulciano, Italy. There is knight's armor to the right of the entrance. Wine bottles decorate the shelves indoors and are displayed in boxes outside the entrance.

If they have space, take a cellar wine tour at Ercolani, my top pick for families with children. Read more about Visiting Montepulciano with Kids.

As you make your way up, stop at one of the many cafès or bars for coffee, breakfast or a snack. I recommended Caffè Poliziano for the most elegant experience but there are several to choose from. Be sure to check out the comprehensive list of My Favorite Cafés in Montepulciano.

Cornetto pastry and coffee on the table at Bar Poliziano in Montepulciano, Italy.
My breakfast I ordered at Caffè Poliziano couldn’t have been more satisfying.

Keep going all the way up to the Medici Fortezza and swing back around to Piazza Grande, where the greater part of your day will unfold from here.

Metal statue of horse in garden area in Montepulciano. There are low hedges and trees.

Traveling With Kids: If you are traveling with children, note that Montepulciano is quite steep and can be exhausting. The Medici Fortezza is a good spot for kids to unwind and play for a bit at the small park. 

Lunch In Montepulciano

Brick building with red awning above Il Teatro restaurant in Montepulciano, Italy. Two tables with umbrellas on either side of the door.

The top of Montepulciano is where the best Montepulciano restaurants are. I highly suggest you pre-book your lunch (and dinner for that matter) at least three days prior to your visit. 

These are my top picks for lunch at the top of Montepulciano

  • Osteria del Conte: Best outdoor seating
  • Il Teatro: Best for couples
  • Acquacheta: Best for casual/family lunch

Learn More: To read more about Montepulciano restaurants, read my in-depth guide to Montepulciano Restaurants.

Afternoon In Montepulciano

Old stone building with wooden door that's an entrance to a cantina in Italy.

After lunch, you can opt into wine tasting at one of the historic Montepulciano wineries. Contucci is the most famous of them all but I also recommend Cantina De’ Ricci and Fattoria della Talosa, which are close by to Piazza Grande.

Hand holding up wine glass with a small amount of red wine. There are wine bottles stacked and displayed behind it.

Wine Tasting Alternative: If you aren’t into wine tasting, check out the Civic Museum, located just off of Piazza Grande on Via Ricci, 10. 

Get some fresh air and choose to either climb the bell tower in Piazza Grande for sweeping views of Southern Tuscany or, if you have had too much wine, just enjoy a panoramic view from one of the many viewpoints just behind the main bar of Piazza Grande. 

At this point, hop onto the trolly that passes through and take the short tour of Montepulciano with a guided audio tour and rest your legs. It will even take you down to the beautiful Temple of San Biagio (a must-see in my opinion!). 

Woman speaking to driver of a red trolley in the Piazza Grande in Montepulciano, Italy.

The trolly will bring you right back to Piazza Grande where you can chill out at the outdoor terrace and relax with an aperitivo before dinner.

Dinner In Montepulciano

Orange wall with metal sign for Trattoria di Cagnano.

After your aperitivo, give yourself 15-20 minutes to get back down to the midtown of Montepulciano for dinner at either Trattoria di Cagnano or Pentolaccia.

Trattoria di Cagnano is a traditional Tuscan-style trattoria serving up local cuisine in a casual yet elegant setting. They are very family-oriented and also have a kids menu!

Pentolaccia is smaller but with equally traditional Tuscan cuisine. I would choose this if you are in a smaller party or a couple. Be sure to pre-book your table and specify indoor or outdoor seating at both restaurants. 

Evening In Montepulciano

hand holding a cone with chocolate and dark brown coffee ice cream in a cone at arms reach infront of sgarbi sign outside of gelateria on street with beige walls.

Finish your evening in Montepulciano with a walk down to the base of the village. The best gelateria in Montepulciano is towards the bottom, Sgarbi. It’s open until 10:30 so if you are up for it, pop in for some of the best gelato in Southern Tuscany before you turn in for the evening.

Tips For Visiting Montepulciano In One Day

View of Montepulciano buildings from afar.
  • Start your day early. I know you are on vacation but Montepulciano has so much to do and see that you could easily spend two days here if you are a wine lover! 
  • Park in lot P1 early (I suggest around 8:30) to guarantee a spot close to the city walls. 
  • Pre-book as much as possible, including dinners and lunches. Montepulciano is extremely busy in the summer and tables go quickly. 
  • Email the cantinas to ensure you get a spot for a cellar tour. 
  • It’s easy to get distracted by all the wineries, storefronts, enoteche and cafes in Montepulciano. If you get off schedule and miss your lunch reservation, check out my Top To-Go Lunch Spots in Montepulciano for a quick, on-the-go lunch. 
  • Montepulciano is a steep hilltop town. Give yourself time to make your way up to the top. 
  • Do you only have half a day in Montepulciano? Check out my Half Day Itinerary for Montepulciano.
  • If walking is not an option, take the FT bus from the autostazione at the base of Montepulciano below the CONAD grocery store up to the top of Montepulciano at the Fortezza.
  • If you visit Montepulciano during the holidays, don’t miss a stop at the Christmas market in Piazza Grande.

Other Towns To Visit Near Montepulciano

Vineyards at Siro Pacenti winery with an amazing view of Montalcino on the hill in the background.

Consider these neighboring towns to visit on your trip to Southern Tuscany: 

Or, visit wineries outside of the town walls, like Avignonesi.

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