4 days in Bologna, Montepulciano & Siena Itinerary

4 days in Bologna, Montepulciano & Siena Itinerary

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Route & dates

Start: Istanbul, Turkey
Fly:  3 h
1
Bologna
— 1 day
Drive:  2 h 15 min
2
Montepulciano
— 1 night
Drive:  1 h
3
Siena
— 2 nights
+3
Train + Bus + Foot + Fly:  7 h 15 min
End: Istanbul, Turkey

1
day
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Start off your visit on the 4th (Fri): steep yourself in history at Basilica di San Petronio, pick up some new knowledge with Academya Lingue, pause for some serene contemplation at Basilica - Santuario di Santo Stefano, don't miss a visit to Piazza Maggiore, then steep yourself in history at Piazza Maggiore, and finally take in panoramic vistas at Le Due Torri Torre degli Asinell.

To find traveler tips, reviews, where to stay, and other tourist information, use the Bologna visit planner.

Istanbul, Turkey to Bologna is an approximately 5.5- hour flight. You can also do a combination of shuttle and flight; or drive. Traveling from Istanbul to Bologna, you'll gain 2 hours due to the time zone difference. While traveling from Istanbul, expect a bit cooler days and much colder nights in Bologna, ranging from highs of 22°C to lows of 13°C. Wrap up your sightseeing on the 4th (Fri) early enough to drive to Montepulciano.

Things to do in Bologna

Historic Sites Classes

Side Trip

Piazza Maggiore
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Piazza Maggiore ©
Piazza Maggiore
Academya Lingue ©
Academya Lingue
Le Due Torri Torre degli Asinell ©
Le Due Torri Torre degli Asinell

1
night
Montepulciano

Montepulciano ©
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Start off your visit on the 5th (Sat): learn about winemaking at Vinoteca Terra Toscana, then learn about winemaking at Azienda Agricola Romeo, and then learn about winemaking at Az. Agr. Poliziano.

To see where to stay, maps, reviews, and more tourist information, read our Montepulciano trip planner.

Traveling by car from Bologna to Montepulciano takes 2.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Traveling from Bologna in October, expect nights in Montepulciano to be about the same, around 15°C, while days are somewhat warmer, around 26°C. Wrap up your sightseeing on the 5th (Sat) early enough to drive to Siena.

Things to do in Montepulciano

Wineries
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Azienda Agricola Romeo ©
Azienda Agricola Romeo

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 5th (Sat): contemplate the long history of Palazzo Chigi Saracini. Here are some ideas for day two: don't miss a visit to Piazza del Campo and then awaken your taste buds at some of the top wineries in the area.

To find more things to do, other places to visit, photos, and more tourist information, refer to the Siena journey maker tool.

Getting from Montepulciano to Siena by car takes about an hour. Other options: do a combination of bus and train; or take a bus. October in Siena sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 7th (Mon) to allow enough time to travel back home.

Things to do in Siena

Tours Historic Sites Museums
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Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

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