Orvieto & Arezzo

Sounds like the making of a pleasant trip. At FCO [Fiumicino Aeroporto], the Trenitalia app is a time-saver for tickets after retrieving yiour luggage.

First thing at the Orvieto station, buy tickets for the funicular and buses at the tabacchi. Note that the funicular across the street goes only partly up to town [Piazza Cahen]. Here are the buses:

Bus 1: Railway Station to Piazza della Repubblica.
Bus A: Piazza Cahen to Piazza del Duomo.
Bus B: Piazza Cahen to Piazza della Repubblica.

Train schedules for day trips:

https://www.trenitalia.com/tcom-en

From Orvieto you can visit Castiglione del Lago and Cortona; from Arezzo Perugia and Assisi [or Spello]. Cortona the stop is Camucia-Cortona. Fixed taxi fare from the station up to the center of town [Piazza della Republica] is €12. If no taxis are present there is a sign with numbers. No amswers, walk up to the cafe and have a drink; they will call one.

One critical Orvieto note: the best gelateria in town is across from the rear of the Duomo on the left side.

Note these are regional trains, which have no discounts, no seat assignments and never sell out. No matter how you buy a ticket you specify a date. On the app or web site, tickets are good for 4 hours from the selected time and are not validated [date stamped]; tickets bought locally are good for the entire day and are validated before boarding.

Easter Monday is a holiday, but that's the only day affected after Easter Day. Cortona would be an obvious day trip choice if you haven't been there. I would prioritize that over Castiglione del Lago. We visited Sansepolcro by bus from Arezzo - kind of a long day. Passing by Anghiari made us think we would like to visit that town. Arezzo is great - we really enjoyed it. (Orvieto too.)

As mentioned, there will be closures on Easter Monday. Some restaurants and grocery stores will be closed.

Are train schedules affected Easter Monday? That day we may use the main Florence to Rome line.

Also, any recommendations on what to see and do in Cortona? Any points to view the beautiful countryside that are fairly walkable once we take a bus up there?

Also, would really like to visit Montepulciano for a day trip from Arezzo. What are the best options? Car for hire seems like the quickest, but I heard it can be pricey, like 120 euro one way? Does anyone know a good private care service from Arezzo? How is bus service from there? How about taking a train down to Chiusi then taking a taxi or bus from there?

I have never been to Italy in April, but I would imagine that this year's train schedule for Easter Monday (April 13) would be a reasonably good guide to what will be available next year (April 5).

You can check this year's schedule on trenitalia.com and italotreno.it.

The two towns are quite different, and there is "more to do" in Orvieto. But I think they are good choices for "no car." You probably should look into local bus service, which I have never used.

One of the charms of Castiglione del Lago is the local lake beach, which is quite busy in hot weather. I don't know if it is open in April (to enjoy the local life .... not so much the swimming!). You would also want to check if the civic Museum is open in April, just because it's not the busiest place in Tuscany/Umbria. But it's a good visit. I've read there is good food there, but we didn't have a meal on our schedule: We were going (by car) to the relatively nearby, Avigonesi Winery, which has a magnificent, open-air, fine-dining, lunch restaurant with wine pairings. If you can get there, I recommend it. Pre-payment required. You won't want dinner that night.

I personally avoid AirBnb because I prefer hotel services, and because AirBnb tends to be harmful to local housing practices. It's no longer the case that starving locals rent out one room to backpack-budget travelers. AirBnb's all have to have espresso machines, WiFi, ice machines ... Units get taken off the rental market and priced so high that local's can't afford to live there anymore.