5 days in Tuscany Itinerary

5 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary planner

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Route & dates

Start: Chicago
+4
Fly + Foot + Bus + 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.
Kick off your visit on the 2nd (Wed): learn about winemaking at Podere Il Cocco, do a tasting at Ciacci Piccolomini d'Aragona, then learn about winemaking at Mate Winery, and finally learn about winemaking at Poggio Rubino.

To find other places to visit, maps, photos, and more tourist information, go to the Montalcino travel route planning tool.

Chicago, USA to Montalcino is an approximately 19- hour combination of flight, train, and bus. You can also do a combination of flight, tram, train, and bus; or do a combination of flight, bus, and train. You'll lose 7 hours traveling from Chicago to Montalcino due to the time zone difference. Expect a bit warmer temperatures when traveling from Chicago in October; daily highs in Montalcino reach 73°F and lows reach 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. On the 3rd (Thu), enjoy the sand and surf at Spiaggia Di Sansone and then immerse yourself in nature at Percorso dell'Enfola.

For photos, reviews, and other tourist information, you can read our Portoferraio trip builder site.

Traveling by car from Montalcino to Portoferraio takes 3 hours. Traveling from Montalcino in October, you will find days in Portoferraio are slightly colder (67°F), and nights are about the same (58°F). Finish up your sightseeing early on the 3rd (Thu) so you can travel to Florence.

Things to do in Portoferraio

Parks Outdoors Trails
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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.
Kick off your visit on the 4th (Fri): don't miss a visit to Ratto della Sabina, don't miss a visit to Piazzale Michelangelo, take in the views from Ponte Vecchio, then explore the world behind art at Gallerie Degli Uffizi, then contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and finally get to know the fascinating history of Piazza del Duomo. Keep things going the next day: steep yourself in history at Basilica of Santa Croce and then admire the masterpieces at Florence Academy of Fine Arts.

To see where to stay, ratings, photos, and more tourist information, you can read our Florence road trip app.

Traveling by combination of ferry and car from Portoferraio to Florence takes 3 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry, train, and bus. In October, daytime highs in Florence are 71°F, while nighttime lows are 54°F. Wrap up your sightseeing on the 5th (Sat) to allow time to travel back home.

Things to do in Florence

Museums Historic Sites
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Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

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