Should I rent a car in Sicily?

The drive from Catania to Taormina is an easy one. Parking in Taormina can be a pain so if you stay overnight get a hotel with parking. I didn’t stop in Messina so can’t speak to driving in it, but the road up to it is fine.

I can't imagine parking in Taormina is easy or cheap. The town basically hangs off a mountainside, so flat spots are at a premium.

Also make sure your $44 deal is all inclusive, Some insurance is required in Italy, plus taxes and other fees add up. Your credit card car rental insurance may not cover Italy, and does not replace the required Liability insurance.

But, if where you are going to look at the family homestead is in the country, then that may be your only option. If just going into Messina to look around, then take the train.

If you find a hotel or apartment rental in Taormina with its own private parking, please let me know! I have been searching unsuccessfully online for weeks.

The drive to Taormina, as throughout Sicily, is easy. We had no problem parking in the Lumbi parking facility, which was the most convenient to our accommodation, and taking the shuttle to the city center which is pedestrianized:
https://www.traveltaormina.com/en/how-to-reach-us/parking.html

@Susan - In Taormina we stayed at Hotel Bel Soggiorno Via Pirandello 60. It is half way up the hill and has its own free lot. The lot can fill up, so an earlier arrival is better. The link is the view of Mt. Etna from the breakfast area.

Thank you everyone!! Super helpful.

@susan we are staying at hotel II piccolo giardino and they shared this parking info after I booked.

"We can offer you a private parking service with valet, at a cost of € 20.00 per day, with active delivery from 08:00 to 20:00 in Via Circonvallazione 14"