Sicily in June. Pinch me!

You could start from here:
http://www.bestofsicily.com/
Rick Steves also has something about Sicily in his guides.
You don't say how many days but Sicily will easily take at least 10-12 days of your time. If you have 18 days again, you may want to add the Gulf of Naples area (Naples, Pompeii, Sorrento, Positano, Amalfi, the islands of Capri, Procida and Ischia, etc) for at least 4 or 5 days.
Sicily is far so I recommend the airplane. Rome has lots of connections to the island. From Naples you can use Volotea airlines. There are also ferries from Naples but it takes the whole night.
For Sicily I also recommend a rental car but not while in the big cities like Palermo, which is too congested.

What Roberto said.

From Naples, you could also consider taking a sleeper train, in a 4-bunk compartment. The train gets loaded onto a ferry for the crossing to Sicily, pretty neat huh?

Arrange to skip Rome altogether with your international flights - only making it a connection point if you must. Look into arriving directly into Naples, then either leaving from Catania or Palermo airport.

Once you know which will be your return airport, then you will know in which direction you'll be headed within Sicily.

If you go home from Palermo, then from Naples you can fly into Catania and drive/bus to Taormina, or take the train and get off at Giardini-Naxos for Taormina. The rental car gets picked up either at Catania Airport or directly in Taormina. It gets returned at Palermo Airport, before you start a 2-night stay in Palermo.

If you go home from Catania, from Naples you can fly or train to Palermo. Stay 2 nights, then pick up a rental car from Palermo Airport and return it to Catania Airport.

Once you know how the flights play out, then you could decide how to: a) split your time between southern Italy and Sicily, and b) plan your itinerary within Sicily.

Last April we went to Sicily and loved it. We flew into Naples went to Sorrento for a few days and headed South. From Paestum we took the train to Milazzo, no problem and the ferry crossing is so cool. If you are going to drive you will want to avoid driving in Palermo, pick up or drop off only. Palermo itself was a pleasant surprise. The interior was beautiful, green with lots of wildflowers and sparsely populated. Do think about the Aeolian Islands, Lipari is a great base. The valley on the North side of Aetna around Francavilla di Sicilia is full of small vineyards with lots of B&Bs and agritourismos. I found the Lonely Planet Sicily guidebook very useful for trip planning. The wine is good, the food is excellent and the prices friendly Go

For our October 2010 trip to Sicily we flew into Catania and based in Taormina for 4 days. Beautiful scenery, fantastic history, spectacular cuisine. It's still my favorite regional food in Italy to date, because it's such an amalgam of Spanish, German, Greek & Arab influences, besides Italian, of course. Took a wonderful private cooking class at one of the restaurants in town, first shopping for foodstuffs at the Mercato Comunale, then back to the chef's restaurant for a hands-on lesson. Intense but great.

We used Sicily Life for a private tour to the nearby medieval towns of Forza D'Agro, Castelmola & Savoca, the latter of which was where the Sicilian scenes in Godfather I and II were filmed. Also, in the fog that day, we toured some catacombs where mummified remains of the town's ancient mayors, priests, etc., are dressed & propped up to be seen. Weird and incredible.

Our next trip to Sicilia, whenever that is, will tour more of the island, because I can tell we missed so much first time around!

Hi Alexandra -- There have been several postings about Sicily lately, so you can probably learn a lot just by scrolling through the Italy section of this forum and reading through those comments.

Also, there have been several long trip reports recently about Sicily that could be helpful. Go to the Trip Reports section of this forum and look for those. Zoe and I both wrote one this past summer, and I remember one from Harold maybe a year ago, and there could be others. I don't think search is working, so you'll just have to scroll through a few pages.

Other than that, my only other suggestions would be to go as early in the summer as you can (it gets hot in Sicily!) and spend as much time as you can. Sicily is a large island, and it takes longer than you might expect to get from one place to another. There are so many wonderful places that your biggest challenge will be deciding what to see and what to skip til the next time!

Have fun planning.

Instead of the search function on this site, use google's advanced search, putting in the RS travel forum (community.ricksteves.com/travel-forum) in the "site or domain" box.

If you are limited to traveling in the summer, bear in mind that southern Italy and Sicily are quite hot then.

Thank you all for your inspiration and helpful tips! I will definitely search through the trip reports. I think we will travel early June after school lets out. Probably fly into Rome and travel to the Amalfi coast for the first leg before joining up with Italian friends to go to Sicily. Ciao!

Here's my Sicily trip report from a trip taken April-May 2015: https://community.ricksteves.com/travel-forum/trip-reports/sicily-palermo-caltanisetta-siracusa-taormina