5 days in Tuscany Itinerary

5 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary planner

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Route & dates

5 days in Tuscany Itinerary

Start: Chicago
+2
Fly + train + bus:  18​h
1
Montalcino
— 1 day
Drive:  3​h
2
Portoferraio, Elba Island
— 1 night
ferry + Drive:  3​h
3
Florence
— 2 nights
Fly:  14​h
End: Chicago

1
day
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 2nd (Wed), do a tasting at Podere Il Cocco, do a tasting at Ciacci Piccolomini d'Aragona, then do a tasting at Mate Winery, and finally learn about winemaking at Poggio Rubino.

To see photos, where to stay, and tourist information, read our Montalcino journey planner .

Chicago, USA to Montalcino is an approximately 18-hour combination of flight, train, and bus. The time zone difference when traveling from Chicago to Montalcino is 7 hours. Plan for somewhat warmer temperatures traveling from Chicago in October, with highs in Montalcino at 73°F and lows at 56°F. Finish your sightseeing early on the 2nd (Wed) so you can drive to Portoferraio.

Things to do in Montalcino

Wineries
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Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Mate Winery ©
Mate Winery

1
night
Portoferraio, Elba Island

Portoferraio ©
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Start off your visit on the 3rd (Thu): kick back and relax at Spiaggia Di Sansone and then kick back and relax at Percorso dell'Enfola.

To see photos, other places to visit, ratings, and tourist information, go to the Portoferraio online journey planner .

Traveling by car from Montalcino to Portoferraio takes 3 hours. Expect little chillier weather when traveling from Montalcino in October: highs in Portoferraio hover around 67°F, while lows dip to 58°F. Finish your sightseeing early on the 3rd (Thu) so you can travel to Florence.

Things to do in Portoferraio

Beaches Parks Outdoors
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Spiaggia Di Sansone ©
Spiaggia Di Sansone

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 4th (Fri): make a trip to Ratto della Sabina, take some stellar pictures from Piazzale Michelangelo, snap pictures at Ponte Vecchio, then explore the world behind art at Uffizi Galleries, then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, and finally get to know the fascinating history of Piazza del Duomo. On the 5th (Sat), you'll have a packed day of sightseeing: look for all kinds of wild species at Wildlife Areas, take an in-depth tour of Basilica di Santa Croce, and then examine the collection at Academy Of Florence Art Gallery.

For photos, maps, traveler tips, and more tourist information, use the Florence trip planning site .

Getting from Portoferraio to Florence by combination of ferry and car takes about 3 hours. Other options: do a combination of ferry and train; or do a combination of ferry, train, and bus. In October, daily temperatures in Florence can reach 71°F, while at night they dip to 54°F. Wrap up your sightseeing on the 5th (Sat) early enough to travel back home.

Things to do in Florence

Museums Wildlife Outdoors
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Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

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