25 day Itinerary for Souther Tuscany and Umbria

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

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..:)

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 :)

Sounds like a great tour! On Day 16, I suggest skipping Montefalco and instead visiting Trevi. I found Montefalco underwhelming. Trevi is more visually impressive, less heavily trafficked, and is in the same general area. I commented on these two villages in a prior post. Gubbio was wonderful.

thank you very much!

Going to Umbria, great, don't miss Assisi.

i ony left it off because i have been there. Thanks!

Some comments about this part of your trip:
Grosseto and Maremma
• Day 1 arrive from rome by car. Rest and sleep
• Day 2 Rest Day. Expore Grosseto 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).

Day 2 The historical centre of Grosseto is small but nice. We spent an afternoon there and liked it.

Day 5 Although it’s a pity not to see Pisa, it’s an outlier for the area. Since you intend to return I’d leave it for a future trip because there’s enough to see without going so far.
For the small inland towns Campiglia Marittima is one of the ‘Borghi più belli d’italia’ and worth a stroll around. Have a look at the cemetery below the town too. “Il Goccetto” restaurant is excellent and reasonable if their limited opening times coincide with when you are there. You can have several courses or ‘just’ a ‘tagliere’. Excellent local products, reasonable prices and a love of food which is almost a mission.
Nearby, Massa Marittima is also nice – a little larger and more to see – in particular the square and duomo. We also liked Sassetta.
https://slowtravelitalyspain.blogspot.com/2021/07/costa-degli-etruschi-may-2021-sassetta.html
You might also be interested in Sasso Pisano/ Monterotondo Marittimo for the geothermal park and ‘Biancane’
https://slowtravelitalyspain.blogspot.com/2021/06/costa-degli-etruschi-may-2021-sasso.html

Day 4 Getting the ferry to Elba and back will take up most of your day. It’s not worth taking your car over just for the day but if you haven’t got a car you won’t be able to see much of the island. Considering the time you have I would visit the bay of Baratti and Populonia, which are panoramic. San Vincenzo is quite modern, a good place to eat fish for lunch and go to the beach (Rimigliano to the south towards Baratti) but otherwise nothing special, you could skip it. Piombino is a little gritty on the outskirts but there are good views from Piazza Bovio.

You have clearly done your homework planning this trip. I’d like to add a couple of “don’t misses” into your itinerary. If you are going to Capalbio, you should visit the Tarot Gardens, a short distance from the town. The works there were sculpted by Niki de St. Phalle and her husband, Jean Tinguely. Also on the subject of sculpture, the coastal town of Pietrasanta is completely devoted to that art. Much of it is outdoors, and can be seen while strolling around.
Pitigliano is special because, pre-WW II, it had such a large Jewish population that it was called, “Little Jerusalem.” Some of the Jewish sights have been restored, and it had gotten a bit touristy when we were there. However, I think it’s still very worth visiting.

@Tinac
Thank you so much. just the kind of thing i was hopig for.
I migh not stay in grosetto the, but will visit.
I will add Campiglia Marittima and thik twice about elba...
appreciate it

@Rosalyn..
Thank you very much. I will add

Wow, that's an amazing amount of travel in Italy, I'm jealous. Given the amount you are willing to drive I think your schedule seems doable. I'll include some places that I've been or have been on my list - some of them inaccessible because I don't usually drive.

Grosseto has definitely been on my list - especially for the Museo Archaeologico e dell’Arte della Maremma - but that may not be your motivation. Porto Ercole along with the Monte Argentario (which apparently was under Spanish rule for a long time) might be interesting for coastal exploration not too far away.

In the Arezzo area you might check out Poppi - a small but critical hilltop castle that might be worth a visit. Stia has a great wool factory museum in an old factory there than is interesting but depending on what you're photographing your interest level may very. I don't know what your photography interests are but in Antica Bottega Toscana just near the big piazza has old school local food goods like cheese wrapped in hay and seeds.

I wish I could offer more but you are in some very specific areas. If I were you I would make a series of posts to the board like "I have 4 days in region X - what are the most interesting/photogenic towns in this area?" for each section of your trip. Hopefully people who have explored each of those regions will chime in with recommendations. You're going all over but looking for deep, on the ground information on each area, by breaking it up you may get better recommendations.

Have a great trip, more than a little jealous,
=Tod

Love your itinerary. I'm doing a similar trip end of April into May this year - 2nd trip to Italy. First time we did Rome, Pompeii, SOrrento, Amalfi Coast, Orvieto, Assisi, Siena, San Gimignano, Pisa, Bevagna, Fabriano, Florence and Venice. This trip we've chosen to explore some new and more out of the way spots, including the Maremma. We will also venture into Le Marche, as well, up as far as Urbino.
Rome 4 nights
pick up car
Orvieto 1 night (2nd time there)
Urbino 2 nights (major cultural setting during the Renaissance)
Cortona 2 nights (visiting Pienza, Montalcino and other towns on the way to Maremma)
the Maremma 2 nights at Marina di Scalino and will visit Massa Marittima and Grosetto)
Elba 1 night (taking the car on the ferry to see a little of the island but staying in Portofferraio)
Lucca 3 nights (visiting Vinci and Carrera for a Carrera marble mine tour)
drop off car
Florence 4 nights
then fly to France for 3 nights in Normandy and 3 in Paris

Hope your itinerary lives up to your vision.

@hiredman
thanks very much for the suggestions... be careful what you hope for or are envious of.. you never know someone's whole story. :)
Thaks again.

@melissagherig Sounds lovely. Have fun!