Two Weeks Itinerary in Tuscany, Umbria and Rome | Italy Hidden Gems

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We were invited to a friend’s beautiful Tuscany Italy wedding in late August. We used this invitation as the opportunity to rent a car and do a road trip to explore many towns in the region. We also visited Umbria and Rome Italy, for two weeks.

We stayed in Tuscany near the famous Val D’Orcia Italy region for the first one and a half weeks by renting an Airbnb apartment in Chiusi, a small but beautiful town in Tuscany on the border of Umbria. We used our base in Chiusi to travel to all the nearby towns we wanted to visit.

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Itinerary of cities and towns visited in order shown in the video:

00:52 - Chiusi
02:21 - Florence
04:43 - Val D’Orcia
05:24 - Salcheto
05:30 - Montepulciano
06:13 - Pienza
06:45 - San Quirico D’Orcia
07:18 - Montalcino
08:00 - Abbey of Sant’Antimo
08:15 - Bagno Vignoni
08:39 - Monticchiello
08:58 - Siena
10:10 - Monteriggioni
10:18 - San Gimignano
11:14 - Castiglione del Lago/Lake Trasimeno
12:43 - Perugia
13:16 - Assisi
14:48 - Orvieto
15:01 - Rome
17:18 - Vatican City

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Tips and Details:
- We received a Fiat Panda semi-automatic rental car that we don’t recommend. The car would take a few seconds to go after hitting the gas pedal. This would cause the car to slide back in the meantime when parked on a hill, which was pretty uncomfortable. It was the only non-manual car available and fully manual cars would probably have been better.
- Wine is very cheap. Five dollar wines are like 15-20 dollar wines in the states. More expensive wines, especially from local shops and wineries are so good that you can’t find them in the states!
- There were charming small shops and picturesque restaurants in Chiusi. Being on a budget however, we bought most of our food at a nearby supermarket called Pam Superstore (Pam Chiusi on Google Maps), which had everything we needed and local products to try at great prices. We bought the most expensive bottle of olive oil for about 10 dollars and it was the best olive oil we had anywhere.
- You can forgo your car at Chiusi Scalo train station or even visit the town without a car by jumping on a train to the town. You can also rent a car at the train station. We walked 25 minutes from our apartment in Chiusi to the train station and didn’t have to pay for parking at the station this way. Some people got fined for parking at the station since it wasn’t allowed.
- Although we saw so many places in two weeks, we recommend consolidating your itinerary and stick to one or two towns per day to get the most out of them. After seeing so many towns, they all start resembling one another, even though they all have very unique things about them that are easy to miss.
- Places we wanted to go to but didn’t: Parco dei Mulini hot springs, Viterbo, Volterra, Sarteano, Spello, Civita di Bagnoregio, San Marino
- Total budget for two weeks including accommodations ($100 per night for entire, large apartments), car rental ($20 per day), gas (not sure but less than $250), food (not sure but less than $500), and train ($100) was under $3,000. This does not include airfare.

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