Sicily

That's a painfully short amount of time to be in Sicily, which is more like a 2- to 3-week destination. You'll need to concentrate on one part of the island.

Are you flying? If so, into which airport and out of which airport? Exactly what time of day are you arriving and departing? Do you have five nights in Sicily?

Are you willing to rent a car?

What are your interests: Greek sites? Picturesque small towns? Medieval city centers? Scenery? Beaches? Churches? Food markets?

If you're not locked into this, I'd postpone Sicily until you can spend more time there.

I would do some research and pick only one region that has a concentration of sites you're interested in to minimize travel time. You can only cover so much in 5 days (probably not even 5 full days, right?). I don't know if you ruled out using public transport but it's fairly easy.

This site has a bunch of ads (unfortunately), but also good info and good road map:
http://www.bestofsicily.com

I agree with the above replies. In 5 nights you won't be seeing "Sicily," but only a small part of it. Depending on what part you pick, you may not want or need a driver. You can drive yourself, or can use buses and trains.

Which part to see, as stated above, depends on your interests. Do you already have your flights? If you do, tell us what they are, as that will determine what parts of the island are easiest to see. Also, what else are you seeing on this trip besides Sicily? This way, people can suggest places that will complement the rest of the trip. For instance, if you're going to beaches on another part of the trip, you will probably want to use your Sicily time for places other than beaches.

Here's my trip report from April-May 2014. I went with a friend and had 10 nights, and we really raced around to "hit the highlights." As you'll see, he did the driving, but didn't find it difficult. https://community.ricksteves.com/travel-forum/trip-reports/sicily-palermo-caltanisetta-siracusa-taormina