A lovely place to visit and a good time. You may find some rain but the big advantage is that the island will not be flooded with tourists (well, unless Israelis descend there while getting away from home). Wineries
By far the most interesting will be Planeta. They have several wineries on the island and you will be receive a warm welcome as the owning family has a fine relationship with Israel. Also very good to visit will be the wineries of Cusumano, Tasca d'Almerita and Donna Fugata, all producing some excellent and interesting wines. Be sure in all cases to phone ahead to let them know when you are coming.
With special regard to Planeta, see my recent tasting notes at http://www.haaretz.com/hasen/spages/1017732.html
If you want to make a few "points" print that out and bring a copy for the family when you visit. Dining Out
Many good trattoria style restaurants in every city and town on the island, and for those best bet is to go by your senses and play your hunches. Three places that I recommend highly:
Principe Cerami, piazza San Domico 51, in Taormina. Excellent traditional food with a distinctly modern touch in an extraordinarily lovely setting. Excellent local wine list. Expensive but worth the investment.
Casa Grugno, via Santa Maria de'Greci 1, in Taormina. Excellent Sicilian dishes with a unique Northern-Italian touch. Good wine list. Moderate-expensive.
Scrivano, via Bonaventura 1, in the village of Randazzo. A super-homey place, nothing complex in the décor but warm and welcoming with classic Sicilian dishes. Moderate prices. My personal favorite in Sicily.Miscellaneous
To read about several traditional Sicilian dishes, see my little piece athttp://www.stratsplace.com/rogov/recipes_of_sicily.html
To read a bit about Sicilian culture and dining habits, the piece athttp://www.stratsplace.com/rogov/sicily_at_easter.html
For a bit more on Marsala winehttp://www.stratsplace.com/rogov/marsal ... oking.html
Have a great vacation!