sicily Italy

Six days is just long enough for one location and day trips or two locations, no day trips. Stay on Ortigia Island, Siracusa’s original ancient location. Take a train or bus for a day trip to a Baroque town such as nearby Noto.
Or split your time between Ortigia Is and Noto, Ragusa, or Modica, the Baroque towns.
Or Palermo with day excursions to Agrigento and Trapani,Segesta and Erice.
There are plenty of day tour exxursion companies out of Palermo. Cefalu is another possible day trip from Palermo.

We love Palermo, and have always stayed at the Ambasciatori, in walking distance from the train station. The train station is where the airport bus will let you off. We love the Ambasciatori, but I have no idea how many stars it has. There's a wonderful rooftop terrace where breakfast is served. Also a restaurant and bar on the roof level. The elevator doesn't quite go all the way up to the top, if that's a concern. The staff is wonderful.

I just wanted to say that a $250 price range per night is probably too generous in most of Sicily, even at a 4-star hotel (the exception being Taormina which is much more pricy and geared toward luxury travel). I stayed in a very nice 4-star hotel (Grande Albergo Alfeo Hotel) although in Siracusa, at a fraction of that price. Sicily in general is not that expensive (especially in comparison to Northern Italy). If you land in Catania, I would highly recommend Siracusa for a few days with perhaps a day trip to Noto and Taormina if you have extra time. Six days is rather short, but you can cover a decent part of one region (but not likely more than that).

We just did the RS Sicily tour, and of the places we visited (Palermo, Trapani, Siracusa, Catania, Taormina), Siracusa (staying in Ortigia) is the one I'd go back to. With maybe an excursion to the Valley of the Temples near Agrigento.

We did a Southern Italy tour/Sicily tour 3 years ago. Our time in Sicily covered the Eastern region. Our tour ended in Taormina. On our own we took the train to Ortigia and spent 4 nights there and did a day trip to the Barogue towns of Noto, Ragusa and Modica. That said, you could divide time between Ortigia and one of the Barogue towns. We spent our last night in Catania. If you chose Ortigia as a base, we can highly recommend a lovely B & B, La Via Della Giudecca. We had an apartment with a patio and view. Very quiet, delicious breakfast. Highly recommended on Booking.com and RS
Forum. We booked directly with the B & B. Walking distance to sites and restaurants. Ortigia is absolutely magical at night.

You haven’t driven on your trips on The Continent, and maybe that’s not a consideration for your time on Sicily, but for what it’s worth, on two trips, we’ve found the driving to be a lot easier than in many place in Europe. Roads are toll-free, and in good condition, drivers are courteous, maneuvering and parking are pretty easy. If you’re not driving, are you planning on booking tours, or using buses for your day trips?

We were able to have more than 6 nights each trip, so were able to fit in more locations. Each time we flew into the Palermo airport, which is actually quite some distance west of the city itself, and picked up our rental car. With enough time to cover some ground, we took the car ferry back to mainland Italy on Trip 1, and flew out of Catania, “open jaw,” on Trip 2, avoiding having to backtrack to the Palermo airport. Stayed mostly in 2-3 star type, less expensive places, which left more money for food and transportation.

Some highlights, some of which can involve steep terrain if you wander much about town, and which aren’t necessarily close to each other, and may not be easy to connect via public transportation within a 6-day timeframe, included: in the West, Segesta, a fabulous Greek temple and theater from when ancient Greeks made Sicily part of their greater empire, and Erice, a wonderful village perched high above Trapani. To the South, Agrigento, a bigger city with an old town up high, and the best collection of surviving Greek temples anywhere. Southeast is Syracuse and the chocolate wonderland of Modica. East is Catania, jumping-off point for volcanic Mt. Etna, and Taormina north of Catania, with magnificent views overlooking the ocean. Interior, at Piazza Armerena, is the Villa Romana del Casale, an amazing Roman Villa with magnificent floor frescoes. Hopefully you’ll have time to see some of these, and the means to get to and from them. They’ll be 6 fabulous nights, with days thrown in!

I was in Sicily two weeks ago. Two things you must realize....it is a hilly place and public transportation is not great. However, it is an amazing place. You might want to look into day tours to get to the major sites.

That time of year it is going to be very hot.

public transportation is not great

But it's still "good enough" and gets the job done, and at pretty unbeatable prices. It definitely underwhelms on Sundays, but both buses and trains took me everywhere I wanted to go in the SE portion of the island. The regional train was a typical local train, not blazing fast and stopped at every station...but it did the trick. Buses were very nice and modern. There are many very good connections via bus from the Catania Airport. If you can't or don't want to drive, you'll still manage.

If you haven’t viewed this, yet, Sarah Murdoch, co-author of the new RS Sicily book shares lots of helpful info and suggestions. I will be taking her class this Saturday at the RS store in Edmonds.

https://m.youtube.com/watch?v=sId0ICT9Wfo

Agnes is right about the prices. I just went back to check, and a couple of years ago we paid €55 a night for an off-season double at the Ambasciatori. I don't know what there rates are now, but even doubled that comes in well under your limit. As I recall, the other hotels we looked at were all under €100.

If you decide on Palermo, we liked Hotel Plaza Opera, a four star hotel way below your price range. We enjoyed Palermo as a city much more than Catania (although Taormina outside of Catania is lovely). We used Alex Travel as a car service for pick-up from the airport to the hotel. We arrived in mid-October last year and it was very warm (although not so warm for swimming). You could consider a staying a couple of days in Cefalu, outside of Palermo which has a nice beach area.

There are places in Sicily that are comparatively flat (Ortygia, the historic section of IrSiacusa; Catania; Trapani; at least parts of Palermo), but it's true that many wonderful places do involve hills.