A month in Tuscany!

Get a guidebook with broad coverage of (at least) Tuscany and Umbria. Rick's books are excellent for the cities and towns they cover, but you really should also have a second book that just plain covers more places. You will have no trouble at all filling your time.

If you have an interest in antiques, you may want to Google for information on the large outdoor antique market held once a month in Arezzo. I believe it's near the beginning of the month, but check.

Yes, the antique market is the first Sunday of the month in Arezzo. They also have a fantastic Jousting Festival that’s the first Sunday in September. There’s also another one the third Saturday of June. It’s a fun all-day event (purchase tickets ahead of time).

I would sign up for a cooking class in Siena for a connection to the local food and also some good practicalities of markets, etc. that might me discussed in the class.

Wow, have a fantastic time!

Very good advice from acraven, and I especially second the tip about Arezzo.

Read everything you can find about driving in Italy. ESPECIALLY about speeding cameras and ZTLs. Don't forget to get your IDLs before you leave home. Remember that you may have a problem finding an open gas station on Sundays in small towns ( usually not a problem on the autostradas or in cities).

Parking in cities can be a headache. When we stayed at an agroturismo we found the car invaluable in the rural areas and small towns, villages. But most times when we day tripped to a city, we would drive to the nearest train station, then take the train into the city. Italian trains are so cheap, this was an easy decision for us.

Hey, and share some stories afterwards in a Trip Report!

My husband has mentioned that he would be open to staying two months in Italy after he retires, so I would love to hear your adventures.

How exciting! I'm jealous!

Brush up on the general traffic rules for Italy, paying attention to signage. If you don't have a Garmin, think about getting one. Buy the Italy/Greece maps SD card. Get a good Michelin paper map as well. Get an International Driving permit.

Pay strict attention to speed limits. There are automated systems to catch you speeding. I'm waiting for the usual suspects to come with horror stories about ZTLs. The are generally well marked and easily avoided. The rule of thumb is anywhere within the walls of a hill town is ZTL.

I avoided driving in big cities like Rome and Florence, but Siena was not a problem to avoid the ZTL and park outside. If you make a trip to Florence, there are plenty of places to park and catch a bus or tram into the city. Taking a train from Siena would be another option.

Splurge for a day and have either lunch or dinner at Castello di Verrazzano. Plan at least three hours for their food and wine tasting. Plan to attend Vespers at the Abbey of Monte Oliveto. It is celebrated in Gregorian chant. The evening we were there it was the monks, a lady from a nearby town and the two of us. It was a moving experience.

I'm already jealous! :-)
-Siena, an amazing place
-San Gimignano, go after 4pm, a lot less tourists. It's a gorgeous village
-Volterra another great one
-Monterigionni, super small but charming
-The road between San Quirico D'orcia and Pienza-Montepulciano is a classic. SP146.
-Pienza and Montepulciano are 2 other gorgeous villages
-Montalcino, go on top of the fortress for amazing views, and inside, there's a nice wine bar.
-Sant'Antimo Abbey and Monte oliveto Maggiore
-Arezzo
-Cortona
-Orvieto in Umbria
Etc, etc
A guide book would be handy for a lot more details

You must be just jumpin' out of your pants excited!! If you are close to a library, see if they have guide books focusing on Italia road trips. For general guidebooks, I like Lonely Planet or Bradt guides for practical advice and covering lesser spots that you now have time to visit.

Tuscany is a place you can put a pin in the map and not really be disappointed. Some of my favorites.

Certaldo near San Gimignano, San Gusme and Brolio Castle by Gaiole. Radiconfani south of Bango Vignoni. Pitigliano. The list just goes on and on.

Recommended checking out the Eyewitness Guide Back Roads Northern Italy book. We have used it to find great roads and places in Tuscany. Many libraries have the book; I ordered a used copy from Amazon. Have a wonderful trip!

Drive the Chiantigianna, SR 222, that runs from Siena to Florence. Visit Castellina, Radda, Panzano and Greve.
In Panzano visit Dario Cecchini’s butcher shop and eat at his restaurants. Watch Chef’s Table, Volume 6, episode 2 on Dario Cecchini. On Netflix. This is the only butcher shop where I have been given wine and appetizers when entering.
Arezzo, see the frescos in the cathedral there. Visit Cortona with views of Lake Trasimeno from it’s hilltop setting. Google ”Hannibal” and see where he marched through Tuscany. Visit Lake Trasimeno; Monte de Lago is a nice town there.
Any chance you’ll be near Siena for one of it’s Palios? Late June 29-July 2 and August 16. It is a fabulous experience!
Visit Montalcino and Pienza.
Have a wonderful month. How exciting!

Thank you so much for all of the wonderful suggestions!! I am overwhelmed with you excitement and support. Yes, we are beyond excited, and want to make sure we make the most of this valuable time in Italy. This adventure has been on our bucket list for a long time, and here it is....I will be and sure and update you when we get back. Thanks for all of the great recommendations!

Learn some basic Italian.
Outside of the major tourist destinations it will become handy.

To answer the question about whether we will be there for one of the Palio's in Siena, the answer is YES!! We were watching the Rick Steve's show on Siena and saw his coverage about the Palio. As soon as we saw the dates, and realized we were going to be there, I started crying. Crazy, I know, but I am simply out of my mind excited. It doesn't feel real yet...

If you are interested in cooking I would highly recommend the cooking class with Nonna Ciana. It was a great experince and takes you back into the old Italian way of cooking and preparing a meal.
http://cookingclassesnonnaciana.com/