Although the "Pearl of the Renaissance" as it is called Montepulciano would probably deserve a longer stay, two days are enough to get the spirit (and the wine) of the town. 

This is my personal itinerary:


After you've checked in to one of our MONTEFELIX apartments or other properties you should start from the historic cellars of 👉  Cantine Gattavecchi (2 on the above map) by the church of Santa Maria then continue up the hill and visit the 👉  old Fortress - Fortezza - (3 on the above map) built in 1200 in the highest part of the town. After a thorough renovation it hosts now the Association of the Wine Producers and offer an incredible tasting room and a beautiful panoramic garden overlooking the surrounding valleys, especially at sunset. You can taste there the wine from the most important local wineries and get many information about the the wine world including arranging further visit to wineries or other monumental cellars. 
So these are definitely the first place to start.

The Fortress in an ancient photo


You should now get acquainted with the town, so from the Fortress start your exploration stroll waking to the near 👉  Piazza Grande (4 on the above map) which is the most beautiful attraction of the town with its pristine Renaissance palazzos, continue then over Via Ricci stopping in  👉  Piazza San Francesco (5 on the above map) another fantastic sunset and view point, take Via del Poggiolo,  then Via di Gracciano until the East Gate - Porta al Prato (the most important gate of the town). Exit the gate and reach the 👉   Church of Sant'Agnese (6), from there you have a beautiful glance of the hill from the East. 
Walk back, pass the gate and walk uphill through the main street and start checking out the restaurants' name, location and menu (it will be useful for later). On the way up feel free to take any side narrow street on your left, many are leading to beautiful terraces looking southward over Chiana valley. By the time you reach the top of the hill again (7) , the city tour is complete and you have an idea of the layout and where most of the amenities (restaurant, cafes, shops) are located. Time to get ready for an aperitivo!


Book your restaurant among those you've liked most during your walk or have a look to my recommendations here (my restaurant list) and head to local's favourite aperitif places:
E Lucevan Le Stelle wine bar and bistro with a terrific (and breezy) sunset terrace. You can also eat there. 
Gattavecchi Wine Bar and Osteria, set in an ancient Friary with a nice sunset terrace, beautiful cellars and good food.
La Dolce Vita Enoteca, possibly the most comprehensive wine bar in town with expert sommelier to help finding your (wine) way.
Enoliteca La Fortezza, the wine producers syndicate tasting room located in the fortress of the town with a beautiful panoramic garden.

After an aperit enjoy a night out in one of the restaurant or osteria (see my recommendations here) and perhaps a night walk through the main street for a gelato.


You may have breakfast in your apartment but don't forget to check out the grand cafe of Montepulciano Caffe Poliziano for a mandatory cappuccino e cornetto (croissant)


Time now to explore the inner part of the town,  or better its guts. Montepulciano is built over a sandstone ground and generations of inhabitants (since Etruscan times) have dig and carved the hill leaving amazing underground constructions.
Unmissable is the 👉   Cantina de' Ricci a maze of tunnels, grotto and gigantic barrels. Other notable cellars are Crociani, Pulcino, Contucci, Talosa and Fanetti.

One of the amazing underground cellar 


If you have a car you may now visit the surroundings of Montepulciano. The countryside around the town offers quintessentially Tuscan landscapes with gentle valleys and hills covered with vineyards, olive groves, lines of cypresses and stone farmhouses scattered here and there. 
A classic itinerary to enjoy this neaty is the tour of wineries and the hilltop villages such as:

👉  Monticchiello, 
👉  Pienza, 
👉  San Quirico, 
👉  Trequanda, 
👉  Montisi, 
👉  Montefollonico.

(just to mention a few) 

The road from Montefollonico to Montepulciano

Guided tours: A Walk with Poliziano and Short Break Visit of Montepulciano

The private company Valdichiana Living – with the contribution of the Municipality of Montepulciano – organises tours to visit Montepulciano. They are short tours which, however, touch on the most interesting aspects of the town. The starting point is Piazza Grande and participants are assisted by a licensed guide. We offer two types of tours, “A walk with… Poliziano” and “Short Break Visit of Montepulciano”, which are guaranteed to start independently of the number of participants. All the information on the two tours is provided below. For more details, info and bookings please call us on +39 0578717484 or email us at booking@valdichianaliving.it.

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