Large wine barrels line two sides of a cantina in Montepulciano, Italy.
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Half Day Itinerary For Montepulciano – Designed by a Local

Last updated on November 14th, 2024

Although Montepulciano is a small village, there is so much to do and see. But what if you only have half a day to visit Montepulciano? 

I have been leading friends and family through Montepulciano for over a decade now from half-day visits to three day extravaganzas.

Let’s walk through the absolute best activities to do in Montepulciano in just half a day based on my years of experience here. It’s impossible to see it all in just half a day but with a bit of pre-planning, this guide will help you make the most of your visit.

This guide can be used either as a morning guide or afternoon itinerary, assuming you will have one meal in Montepulciano, either lunch if you spend the morning or dinner if you spend in the evening here. 

Good To Know: The best part of Montepulciano can be seen by foot, as you give yourself a walking tour of the small village, which is the base for this half day itinerary in Montepulciano. 

Half A Day In Montepulciano Overview

TimeActivityGood To Know
8:30 amArrive and ParkPark in lot P1 at 8:30 to guarantee a spot close to the city walls. 
9:00 amWalk from Port al Prato to MidtownMost stores won’t open until 10:00 am but you can stop in on your way back down
9:15/30-10:00Coffee breakStop for a mid morning coffee and breakfast at one of the many cafés.
10:00Walk up to Medici Fortezza and swing back towards Piazza GrandeWalk first to the Fortezza and then head back to Piazza Grande to save steps and time!
10:30Enjoy panoramic views behind main Bar in Piazza Grande If you are very athletic, consider a quick climb up the clock tower.
11:00 Wine tasting / Trolley tourEnjoy a free wine tasting and underground wine cellar tour at Contucci or Fattoria della Talosa. For families and kids, consider a trolley tour instead of wine tasting, leaving from Piazza Grande.
12:00/12:30LunchChoose From: Osteria del Conte, Il Teatro or Acquacheta 
2:00 pmWalk back to base of Montepulciano and end your dayThis is your chance to swing into shops for souvenirs and gifts. 

Arriving In Montepulciano

Huge stone wall with large archway in Italian village.

I suggest making the most of your short time in Montepulciano by arriving at around 8:30, which will make parking a breeze. Lot P1, at the base of Port al Prato is sure to have space that early. 

Start making your way up to the top of Montepulciano, which is quite a hike. Note that most stores will be closed or just be opening when you start your tour around 9:00 am. Take note of anything that you wish to come back to on your way down as you are going to take the same route upon your return. 

Early Morning In Montepulciano

cappuccino and brioche with sugar on wooden table at an Italian bar
My favorite Italian breakfast to order: a brioche vuoto (plain pastry) with a cappuccino

Break up the walk to Montepulciano with a light breakfast and a cappuccino at one of the many bars along the way. You can read about My Favorite Cafés in Montepulciano.

Two men working behind the bar at a cafe in Italy.

I suggest Caffè Poliziano for the best and most beautiful experience but if you have kids, opt for Palazzo Avignonesi Caffetteria or Da Pulcinella Bistrot.

Continue your walk up to the Medici Fortezza and then swing back to Piazza Grande, which will take a bit of time with all the uphills. 

Late Morning In Montepulciano

Sign for Talosa Winery on a brick wall to right of gated doorway.

Finish your morning with an underground cellar tour and wine tasting at one of the historic cantinas around Piazza Grande. There are many, but I recommend Contucci and Fattoria della Talosa.

Both of these wineries offer self-guided wine cellar tours and free tastings. Contucci also has an easy going enoteca right on Piazzas Grande if you want a more curated wine tasting with local products such as pecorino cheese

For families or visitors who wish to opt out of wine tasting, I suggest you hop on the trolley that leaves from Piazza Grande, taking you on a grand tour of Montepulciano, including the Temple of San Biagio with an audio guide. The whole tour, if you don’t ever get off, takes about 30 minutes but the “hop-on, hop-off” ticket allows you to get off at four different spots and get back on at the next trolley. 

Tip: If you visit during the Christmas holidays, don’t miss the town’s Christmas market in Piazza Grande!

Lunch In Montepulciano

Wooden and glass door entrance to a restaurant set in a stone and brick building in Italy.

There are so many Montepulciano restaurants to choose from but I recommend pre-booking a table at one of the following around Piazza Grande: 

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

Good To Know: If you are in a rush to pay because you have something planned in another town for the afternoon, just get up and go to the register to pay just as you have finished. You don’t need to wait for them to bring you the check. 

If you don’t want to sit down to a restaurant in Montepulciano, consider getting lunch to-go with my recommendation in The Best To-Go Lunch Options in Montepulciano.

Finishing Your Visit To Montepulciano

Packaged cheeses on display in a refrigerated area in a cheese shop in Tuscany.

After lunch, make your way back down down to the base of Montepulciano and stop at any of the shops you had eyed on your way up. 

For pecorino cheese, I recommend the Cugusi cheese shop and other food souvenirs and wine to bring home, check out Alimentari Enoteca Lo Sfizio.  

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.

Gelato Lovers: If you love gelato, don’t miss Sgarbi, located towards the base of Montepulciano on your way out. They have some of the best gelato we have had in the area!

Other Towns To Visit After (Or Before)

Stone church in Italian village with statue of two men wrestling in front.
San Quirico d’Orcia can be visited in just an hour or so, making it the ideal town to pair with Montepulciano.

Consider these neighboring towns to visit in the same day:

Or, visit a winery in the Montepulciano countryside like Avignonesi.

Have more time? Read my One Day Itinerary for Montepulciano!