Day trip options out of Cortona!

For signage, traffic cameras and general rules of the road, read this and download their book.

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

Head to your furtherest location of the day first, eleminating long drives back to your lodging in the dark.

Since this is your first trip, print out individual maps of Cortana-San Gimignano then a second map from San Gimignano to Siena. Do this for each segment of your drive. Use
https://www.viamichelin.com To do this.

One thing you need to be aware of is the drinking limit in Italy is .05, much lower then the US. If you find wine you like, buy a bottle or two and enjoy it in your lodging in the evening.

Driving issues, ZTLs:

http://driventoit.blogspot.com/

Be sure to get the IDP. Where are you picking up and dropping off the car? What does the Camucia-Cortona train station have to with this?

Ok Monteoulciano and Pienza [lunch at Latte di Luna], but forget about SG--spend the day in Siena. All these towns you park outside and walk in.

Eats in Cortona La Buccacia.

Print out a google map of Cortona, have the hotel people advise you where to drive and park. The center of town [Piazza della Republica] is way up the hill, and you need to park above that and outside of the ZTL. I assume they can recommend places for dinner that are easier to get to. This illustrates why we stay in towns, avoiding driving around at night.

Point 6 is very confusing.

Your drive to Cescina will take you very close to San Gimignano, check with your friend to see if this is part of the area they wish to show you. Or stop there on your way to Cescina.

If it is, visit Siena and Monteriggioni or Castellina or Radda.

Some of your destinations, like Siena and San G, are not right next to Cortona. It will take longer than you think to drive there. (Start with an online estimate and add 15 %) I guess because it's September it won't be as hard to find a parking space as it is in summer. But both of those towns have official parking REMOTE from the UPHILL town. So allow time for that. I personally would not combine such a big place as Siena with another town in one day.

It is true that there are no substitutes for Siena and San G! I'll just mention that, nearer Cortona, we enjoyed Castiglione del Lago (with swimming lake), and a half day with gourmet, lavish, prepaid sitdown lunch and winery tour at Avignonesi. Of course there are cheaper winery experiences. But we chose to have our large meal at lunch.

Edit: When renting a car in a hill town, it's important to know if the agency (and the train station) is at the bottom or the top of the hill. The other question is just how close to your hotel you may be able to park the car while you have it.

I've never had the benefit of a rental car in Europe, and I know that makes it much easier to string together multiple destinations on a day-trip. But I agree that Siena + San Gimignano sounds like a lot for a day, especially since you are interested in relaxing meals.

I don't know whether others overlooked the question about the drone or I'm just behind the times. I don't know that that will go over well. C'mon, folks, what do you think? I have no information or experience to back up my concern.

Point 6 was about the train station as that is how we are arriving and departing the area. We are getting picked up at the station from a local rental car business to take us back to their shop to do the paperwork, get the car. I didn’t know how big it was to be able to locate the person picking us up.

I’ve seen countless videos via YouTube or Instagram and a drone is being used for the shots. I wasn’t planning on flying it within the walls, but somewhere outside the city to get big panoramic shots and videos of the city and countryside, as well as down in Positano later on our trip. Was just wondering about regulations on this.

Have you checked with TSA rules for taking a drone? I'd check with them first. Or Italys rules for flying one.

Quick search brought up these two sites.

https://improvephotography.com/44854/drone-carry-on-laws-batteries-packing-tsa/

https://www.tomstechtime.com/italy

ESounds like Sixit; not a major agency. Beware, read reviews. Avis in Arezzo very good.

We spent a week in Cortona 6 years ago.

Montelpulciano is a great day trip, visit a couple nearby wineries/ could combine with Siena.

I’d spend 1 day in Cortona just to take it in, stop at cafes for coffe, snacks and wander to the top if the town. We also did a fabulous cooking class at a woman’s home- a full day event and was fabulous.

Cortona is a fabulous little town and we will be going there for the third time next may. Trattoria Dardano on the same street was absolutely one of my best dinners in Italy, and very reasonable. The town is so beautiful, especially at sunset and dawn, make sure you enjoy the vistas. Also, since you are driving be vigilant about the ZTL’s. We have driven there twice and although our hotels assured us we could drop off our luggage, we never ventured in the ZTL’s within the town (park at the walls).