JES

And any hotel recommendations would be appreciated too. Small, charming with great local character if possible.
Thank you in advance

Mimar

When are you going (what time of year)? What are you interested in doing? What is your budget?

TDudette

Read about Palermo and Taormino and pick between those two IMO. If neither of those call out, try Siracusa.

For your timeframe, Palermo might be more efficient in terms of travel and taking a side trip to Monreale, but Taormino is perhaps more scenic and intimate.

From where are you traveling? Hot weather? One of the islands? Other posters can tell about those.

JES

Thank you for your responses and advice so far. Sorry, I'm going the first weekend of May.

gertie3751

I reckon either Palermo or Siracusa. From Palermo you can get to Monreale and Cefalu, even Agrigento if you want to spend a day doing that. Plus all kinds of stuff in Palermo itself.
Using Siracusa as a base you can see Taormina in a day (vastly overrated in my view) and get to Noto and Ragusa, even Catania and Etna. Stay in Ortigia of you want a charming medieval town atmosphere.

ekscrunchy

Siracusa.

You are going for a short time, so limit your sightseeing to one corner of the island.

This hotel would fit your needs well; they are very helpful and the place has charm:

http://www.sistemia.it/domusmariae/english/albergo.htm

zeppole

You really need to post more information to get good advice. Are you flying into Palermo or Catania or taking a ferry or train? Do you mind a lot of other tourists? Do you want stunning beauty or stunning sights or a unique experience that bypasses most of the tourists? You want a beach?

The cities of sicily are real cities. Nothing small about them, and charm is in the eye of the beholder. You might do some google searches for Modica or Ragusa, Ortygia, Cefalu and Castelmola and see if anything rings your bell.

TDudette

Forgot about hotel-in 2002 in Palermo we stayed at Cristal Palace that describes itself now as elegant at its site but it wasn't a word I would have used then. It was fine and within walking distance of big theatre. We took taxi to Monreale and bus to Mondella.

(http://cristalpalace.hotelsinsicily.it/?source=googleh)

In Siracusa, it was a Holiday Inn but it was inconvenient to most things. At least a 30 minute walk to Ortygia area.

We found the 3 bus systems in Palermo rather confusing-different ways/places to get tickets. Part of the fun though.

JES

Thank you for all of the great advice. Ekscrunchy, I agree with picking one area since I have such limited time for this trip, and your hotel recommendation looks great. In terms of other questions, I can decide on fly, train, drive I think after picking the best location and see what makes the most sense dependent on that. I will be coming from Milan so I will probably fly into whichever airport is closest to the destination I want to go and get a car from there-if that's what's recommended.

zeppole

Can you fly direct to both Palermo and Catania from Milano?

From Palermo airport, there are some destinations where it wouldn't make sense to rent a car. Less so for places like Ortygia, or the "Catania" side of the island.

nametaken

Sicily is a lovely, historic island and,as you probably already know,deserves more than a long weekend to explore all the charming places. My trip there was for 17 days--I was lucky. However, for your time frame I would opt for Palermo with maybe a side trip to wherever you wish. The markets there are fun, and the historic areas(Greek, Roman, Norman & Spanish) are there for you to explore. Check out a travel guide such as Eyewitness to Sicily and see what you are interested in seeing. Monreale cathederal is a must see. Have a great time;Sicily is wonderful.

zeppole

I don't understand why, when a poster says they want a small, charming town as a base, they are steered toward a large, chaotic city.

nametaken

Poster asked for a hotel recommendation for a small, charming place, not a charming small place as a base. Check it out.

JES

Zeppole & nametaken, you are both right...
I didn't clarify that I actually would prefer a small charming place as well as hotel.
I want a place with stunning beauty and unique experience that bypasses that of most tourists per Zeppole's question above. I want more of an authentic local experience than being one of many tourists.
I guess I'm now considering Cefalu, Taormina, & Syracusa.

Zerlina

Taormina offers stunning beauty (the view rather than the town itself) but it is wall-to-wall tourists.

I've stayed in Cefalu, Modica and Ragusa, but I think you'd be hard put to find enough to do even for a long weekend in any of them. From Siracusa, there is frequent bus service to the Baroque towns, including Noto, a World Heritage city not yet mentioned.

nametaken

Perhaps you could consider a long weekend on the western coast of Sicily. There is a charming, comfortable pensione there that serves a tasty, gourmet evening meal at a very reasonable price. Pensione Tranchina in Scopello meets all your requirements. It is very popular with travelers who like to go off the beaten track. In the vicinity there is an assortment of places to see--Erice, Segesta, Selinute and even Agrigento. If you prefer to hike and explore there is a nature preserve next to the Pensione. You will need a car. The guest house is a short drive from the Palermo airport. I would suggest you check their website Pensione Tranchina, and if you are interested you can rent directly with the owners.I loved the three days we spent there.

zeppole

JES,

Check out Castelmola above Taormina. You can escape the tourists but still get the stunning beauty. With a car, you can be adventurous, in the direction of Etna or small towns around Messina.

I don't have Zerlina's problem with boredom in the Baroque towns for a long weekend. I could spend weeks there. Noto has had a problem with its best sights being covered in scaffolding, but perhaps that's over now, but I would check. You don't get stunning natural beauty in Modica, but you do a get a real town with great food.

Siracusa is nicely located, but I didn't see a lot of stunning beauty to the town, but maybe I was in the wrong part of town. The island fraction called Ortygia has a nice personality, although its beachy-boutique in some parts, like typical high-toned American beachy towns (think a Sicilian Cape Cod? Just joking Fodorites!)

I also think that finding an off-the-beaten track place with meals might work for you. I have this fascination with this place I've never been to: Sant'Angelo Muxaro, near Agrigento

(be careful where you open this site -- it has a soundtrack)

http://www.valdikam.it/en/valdikam.htm

Another area to look for an agriturismo or pensione would be near Lo Zingaro nature preserve, I would think.

http://www.thinksicily.com/Villas-ne...o,-Sicily.aspx

zeppole

I think this place looks lovely, with a car. It's not far from nametaken's suggestion.

http://www.casecolomba.com/testiing/galleria1.htm

Mimar

I really think Taormina is where you want to stay. Shouldn't be too crowded in the beginning of May. We're planning to stay at this hotel on our upcoming visit: www.hotelvillaschuler.com. It comes recommeded at www.tripadvisor.com as do several other options.

JES

These are all fantastic recommendations, thank you so much. I have briefly perused the links and love everything. I will buckle down to make some decisions now.

Another question. While I know the food is going to be incredible everywhere, is there a certain area of Sicily it is known to be exceptional?