4 days in Bologna, Montepulciano & Siena Itinerary

4 days in Bologna, Montepulciano & Siena Itinerary

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Route & dates

4 days in Bologna, Montepulciano & Siena Itinerary

Start: Istanbul
Fly:  3​h
1
Bologna
— 1 day
Drive:  2​h 15​min
2
Montepulciano
— 1 night
Drive:  1​h
3
Siena
— 2 nights
+2
train + tram + Fly:  7​h 15​min
End: Istanbul

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, enjoy the scholastic atmosphere at Academya Lingue, contemplate in the serene atmosphere at Basilica - Santuario di Santo Stefano, then don't miss a visit to Piazza Maggiore, then steep yourself in history at Piazza Maggiore, and finally enjoy breathtaking views from Torri degli Asinelli e Garisenda.

For more things to do, maps, photos, and tourist information, read our Bologna trip itinerary builder website .

Istanbul, Turkey to Bologna is an approximately 5.5-hour flight. You can also do a combination of shuttle and flight; or drive. The time zone difference when traveling from Istanbul to Bologna is minus 2 hours. When traveling from Istanbul in October, plan for slightly colder days in Bologna, with highs around 22°C, while nights are cooler with lows around 13°C. Finish your sightseeing early on the 4th (Fri) to allow enough time to drive to Montepulciano.

Things to do in Bologna

Historic Sites Tours Classes

Side Trip

Piazza Maggiore
Find places to stay Oct 4 — 5:
Highlights from your plan
Academya Lingue ©
Academya Lingue
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): do a tasting at Vinoteca Terra Toscana, then do a tasting at Azienda Agricola Romeo, and then do a tasting at Az. Agr. Poliziano.

For maps, reviews, and more tourist information, read Montepulciano trip planner .

You can drive from Bologna to Montepulciano in 2.5 hours. Alternatively, you can take a train; or take a bus. When traveling from Bologna in October, plan for a bit warmer days and about the same nights in Montepulciano: temperatures range from 26°C by day to 15°C at night. Finish up your sightseeing early on the 5th (Sat) so you can go by car to Siena.

Things to do in Montepulciano

Wineries
Find places to stay Oct 4 — 5:

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 5th (Sat): steep yourself in history at Palazzo Chigi Saracini. Get ready for a full day of sightseeing on the next day: make a trip to Piazza del Campo and then indulge your senses at some of the top wineries in the area.

For other places to visit, reviews, and more tourist information, read our Siena day trip planner .

Getting from Montepulciano to Siena by car takes about an hour. Other options: take a train; or take a bus. In October, daily temperatures in Siena can reach 26°C, while at night they dip to 15°C. Finish your sightseeing early on the 7th (Mon) so you can travel back home.

Things to do in Siena

Tours Historic Sites Museums
Find places to stay Oct 5 — 7:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

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