Le Marche.

My Venice tour guide in 2021 told me that Le Marche is a great place to live if you want to forced to learn Italian, because English is much less widely spoken there than in Tuscan cities with a large English-speaking expat population like Florence, Siena, Lucca.

So for your purposes (not knowing Italian), I would steer you to Tuscany but I am interested in what others think.

The region is just like anywhere else in Italy - people who work in the tourist industry (hotels, restaurants, museums and such) speak English. Maybe not as well as more visited areas, but it shouldn’t be a problem. Just don’t expect older adults to be fluent.

“You say Le Marche and you know that makes me smile
I haven’t seen Le Marche for a little while” (sorry Jackson).
I’ been to Le Marche 3 times all in October/November. It is beautiful with charming villages, beaches, and the Sibillini mountains. The cuisine is wonderful. In the fall there are truffles, mushrooms, castagna and colorful vineyards. I have basic emergency Italian and never had a problem. Ascoil Piceno and Urbino are world class renaissance towns. Not being mentioned by RS just means you have to do some research on your own and there will be fewer people.
Brad

Love this input. I’m putting less-crowded Le Marche on my future-travel list!
fritzfreud I hope you have a wonderful time wherever you choose.

I've visited both, and honestly you could flip a coin--both are fantastic, and I would not worry about the language issue or the driving issue. It's rural driving in most of both for the interior bits, but we made use of the zippy highway along the coast on both trips. If you can navigate a traffic circle, you can drive in Italy.
If you can get equally good flights into Ancona, October would be a great time to visit (for either though--Marche certainly less crowded).
If you were interested in doing something somewhat similar to your Tuscan plan, you could hike on the coast at Sirolo/Numana on the Monte Conero peninsula instead of CT. You could visit the spectacular Frasassi Caves instead of Carrara. Then do the hill towns. You can sub Urbino for Florence/Siena.
I stayed in Ascoli Piceno (great town!), Senigallia (an old town on a beach, great seafood), Fano before the flight out (cute little town), and a small town called Sassoferrato.
Blue Guide is usually the most comprehensive. There are some past threads that share the Marche books that are available (or just go to you know where).
I do think the first segments of your Tuscan plan would actually be easier without a car, then get it in La Spezia.

Le Marche region has a lot to offer. The countryside is pleasant with small medieval towns and villages on hilltops. Similar to Umbria as a region as regards landscapes.
Compared to Tuscany
- a lot less tourists
- but you don't see so much those picture postcard perfect landscapes of hills and cypresses and worked fields and tiny villages.
- not so much the wow factor as Florence-Pisa-Cinque Terre, which will be busy.......
It depends if crowds really bother you or not.......Everywhere is quiet first thing in the morning and busier at the weekends........

Our favourite towns nelle Marche in order:
Urbino
Ascoli Piceno
Loreto for the sanctuary
Osimo
Jesi
Parco Naturale del Conero with Sirolo and Numana
Ancona
Recanati
Seen 30 years ago so not in the ranking: Fermo

Here were some of our highlights to give you an idea.
https://slowtravelitalyspain.blogspot.com/2019/09/day-2-urbino-fermignano-gola-del-furlo.html

https://slowtravelitalyspain.blogspot.com/2022/11/jesi.html

https://slowtravelitalyspain.blogspot.com/2019/11/ascoli-piceno-and-villa-rosa-di.html

IMO:
Parco Conero hiking and Sirolo/Numana v. Cinque Terre: 2 totally different experiences, the only thing in common is that they're on the coast.
Frasassi caves are probably more interesting the Carrara marble quarries.....
Urbino is beautiful but it's not Florence or Siena......

Hi,
the Marches are not a very touristic region but it has really have a lot to offer. These are the places that in my opinion you should consider to visit in the region where I live
- Ascoli Piceno
- Monte Conero and Sirolo
- Urbino
- Fabriano and the Frasassi caves
- Macerata and the archaeological park of Urbisaglia
If you come in October, visit the magnificent forest of Canfaito and the white truffle fair of Acqualagna!
Try the ciauscolo and the vincisgrassi ;)
I strongly advise you to rent a car, forget about public transport!

Thank you for all the very helpful suggestions and information. We look forward to any future contributions.

We have visited Marche several times in the fall and have always enjoyed it. But based on your description of what you are hoping to do earlier in the trip, I would say stay in Tuscany. Driving the Tuscan countryside is fine. With any cities, I’d plan to pay for parking.