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25 day Itinerary for Souther Tuscany and Umbria

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Hello Everyone. I know you get lots of the same questons about Tuscany and Umbria. I have been reading and watching and planning. I would like to run my plan by you all for some quick feedback/ critique.

I am planning a solo 25-day trip through Tuscany and Umbria for September

I am an American and have seen much of Italy already. As for Tuscany, I have visited Firenze, Lucca, Siena, Volterra, San Gimgiano, Cinque terra, and Assisi in Umbria. But, I have not really “grokked” Tuscany and Umbria. I want to do a more thorough survey.

What I really am looking for is beauty, authenticity, education (art/history) and also some of the major “must be seen/ iconic spots”. I am really trying to get the best feel for each region of the country.. and may someday look to spend much time there….so, I am also looking for the area that I feel most optimal for me.

I am an amateur travel photographer (love it) and just love to marinate in beauty and learn new things. I typical drive myself and usually hit any UNESCO sites that are near my itinerary. I like vineyards to look at but I am not a drinker.

I have been doing some research and I am feeling that 25 days would allow me focus on a few areas. I am flying into Rome, renting a car and driving (Flight and Car).

I was thinking of the following:
1.) Maremma and the Mediterranean Coast (5 nights)
2.) Val d’Orcia with a reach north into Chianti area for a day (5 nights)
3.) Southern Tuscany. Orvietto area (3 nights)
3.) Umbria 2 locations, Spoletto area (6 nights) and Perugia area (5 nights)
4.) Rome – (1 Night)

I have read many post about the region and do not want to be redundant. But I thought I would toss my tentative itinerary out here and see if there is any feedback
. Any would be appreciated…

Questions: Are these the best general areas? Anything on my list not worth it? Anything else that should be on my list. Ay other ideas? Tryig to do too much? Probably yes… Of course, If I cannot see all this, I accept it. I Sort of tossed everything I heard good thigs about and grouped them by areas.

Grosetto and Maremma
• Day 1 arrive from rome by car. Rest and sleep
• Day 2 Rest Day. Expore Grosetto and surrounds, beach?
• Day 3 Castiglione de la Pescia, Maria di grossetto, Maremma park
• Day 4 Capalbio, Elba?, San Vicenzo?, Maremma park, populonia,
• Day 5 Small towns inland: (Will research these).(or beach) (or maybe to pisa vis train for day).
Pienza (UNESCO) and Val D’orcia (UNESCO)
• Day 6: Drive check in and explore Pienza
• Day 7: San Quirico d’Orcia, Montalcino, Buoconvento, Monteciao?, Abbazia di sa galgano?, etc. monticcelo
• Day 8: Montepulciano, Bagno Vigoni, Montalcino,
• Day 9: Drive the famous Chianti drive above Sienna ) certaldo, monteriggioni, montefiorale? Maybe revisit Sienna?
• Day 10: Rest Day and driving through small towns I missed in Val dorcia. Or monticello or Radicofani Fortress or Castiglione d’orcia
Orvietto (or around there) (on tentative UNESCO list).
• Day 11: Drive to and Explore Orvieto
• Day 12: Explore Orvieto , la scarzualla monastery?
• Day 13: Explore Pitigliao, Sorano, Sovana,
Spoletto (Unesco Cathedral)
• Day 14: Drive to Spoletto and explore and check in Spoletto
• Day 15: Terni and surrounds, montebuono?
• Day 16: Spello, Montefalco, Bevagna,
• Daay 17. Amelia and Narni, Stronconi
• Day 18: Piano Grande di Castelluccio Norcia, casteluccia and other towns?
• Day 19: extra rest day to go back anywhere I missed or want to revisit
Perugia (or around there)
• Day 20: Explore Perugia
• Day 21: Gubbio and perugia
• Day 22: Arezzo, san sepulchro, subbiano, Anghiari,
• Day 23: Cortona, lucignano
• Day 24 extra day to see anything I missed.
• Day 25: drive back to rome and enjoy rome. Maybe stop in viterbo (Tarquinia, UNESCO Etruscan tombs) on the way? And or ceverteri (UNESCO) or montebuono
ROME
• Day 26: fly home
Thank you for reading.. Am i good?

Posted by
1311 posts

Just an observation - not a criticism of your schedule or planning which looks thorough, but maybe you haven't grokked Tuscany yet is because you haven't slowed down to Tuscany speed yet.

For background I am a super planner, spreadsheet, deep research kind of traveller in general. I know what museums are where and what days things are open, closed, free and the busiest. Potential day trips and alternate activities are planned for most days with transportation options included.
I was in the middle of planning a trip to Italy when our friends said "We got a place in Tuscany for week and it's got a bunch of rooms so come stay." So we rented a car in Orvieto, did Rick's heat of Tuscany drive and stayed in farmhouse a little outside Castellina in Chianti back when it was trying hard to get on the tourist map. And the first couple of days went as you expect with exploration of the town, trips to Siena, Florence and San Gimignano etc.

But after about 5 days something strange happened and I would look at the map for Greve, Rada or Pienza and it seemed really far away. And I would argue with myself "But it will be beautiful there and have great wines!" and I would pushback "But is beautiful here and we already have really good wine." And we spent our last full day in Tuscany buying prosciutto, boar salami, bread and cheese in the local stores and then "wasted" the entire afternoon in a hammock overlooking vineyards watching the clouds pass over the horizon eating, drinking and napping. And it was one of the best vacation days ever.

Now, looking back on it - still never haven gotten to Greve - I wonder who that person was and what he was thinking, but at the time Tuscany had seeped into me and there was nothing else to be done. In one of her later books Frances Mayes describes how distances stretch out in Tuscany and places you can literally see from where you are seem really far away. And how simple errands seem to become too difficult to manage and are clearly best left for tomorrow. It sounds made up but I have experienced it firsthand and "Tuscan time" is a real thing. American me does not recognize Tuscan-tinged me in retrospect but at the time I had no other choice.

Just one personal anecdote. I hope you find exactly the trip you're looking for,
=Tod

Posted by
9 posts

I do understand your point, thanks!

I dont think I am as much a "spreadsheet person" as you describe yourself to be.
This is as far as I go with planning.
I do drive myself around and am quite open to un expected changes and serendipity.
This is also an initial stage of a possible real estate purchase.
I promised myself that I wouldnt choose a villa or apartment until i had surveyed the Italy that I have come to love.
At the end of 2025, if God allows it, i will have driven 20,000 miles just in Italy.

I expect to return for decades to come and be much more relaxed.
Also, i am falling in love with photography... so moving around to see things is fun for me.
And, if i get tired, i will purge places from the list. :)
I like to create a wireframe and give myself complete license to vary it or abandon it.
Also, no nice friends have invited me to crash at a house i tuscay for a week and i am also travelling solo. :)

But, honestly, thanks for telling me your experiecnce and, believe me, it wont be forgotten..:)

Posted by
9 posts

But, given that i am ..hmmm.. motivated... and that i will jettison what doesnt fit, does it seem like way too much?
Basically, if it looks sensible, i will book rooms for these alloted days and then just fit in what i can in each location :)

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