We had an amazing trip to Sicily! We liked it even better than we expected, and we had very high hopes. I spent months reading these forums and keeping up with nearly every post – and all that planning paid off. Just the few tips here and there from all of your posts made our days so much more enjoyable! And of course, all the great advice from Vagabonda was invaluable – I could not believe it when I looked at my profile before I left and saw how many questions I had asked! Hopefully something here will help everyone else that is lucky enough to be planning now! I have written separate reviews of the hotels and restaurants, but this will make a few general observations, and then hit the high points of our itinerary.
Vagabonda: First, one more note about Vagabonda... everyone in Taormina wants to know who he/she is!!! If you mention Trip Advisor, they immediately start talking about her and the influence she has. It can be pretty funny because everyone is afraid of getting on her bad side.
Where to Stay and When to Go? The best way to see Sicily if you want to hit all the major sights clearly would be to travel around every few days. However, we prefer to get to know one place more in-depth and moving hotels a lot does not mesh well with child travelers (we were there with our children, ages 10 and 12). We also expect that we will return to Sicily soon (and now we know we want to!), so we did not feel compelled to see “everything.” We had to go in August for school/ work/sports reasons, and because this was our only real vacation of the summer, we wanted to spend some time on the beach at a nice hotel as part of our trip. We decided to base in Taormina for convenience, choice of restaurants, and the nice beach resorts, do day trips from there, and focus on Eastern Sicily. We spent 5 days staying in town (Hotel Villa Carlotta), and then 5 days staying on the beach (Hotel Villa Sant’Andrea).
Language. My family is Italian (my grandparents come from Sicily) and I studied Italian (a long time ago), so I speak some Italian and understand a lot more. I do think this helped – many people, including at some of the tourist sites and definitely in the stores and in the less touristy areas, did not speak a lot of English. Everyone gave it a shot and was also very kind about my attempts to speak Italian. We didn’t have any communication problems as a result, but if you know no Italian at all, you might occasionally have trouble communicating your point or getting information you want.
It’s All Relative. One general observation before I start is that what you think of Sicily depends on what you expect and what perspective you have. We are coming from Washington, DC. So...was it hot in August? Yes, but no hotter than it was at home. Was it expensive? Taormina may be expensive for Sicily, but most things cost significantly less than they do in DC. There also were a wide variety of options, at all price ranges, everywhere we went. Was it crowded? To be honest, we didn’t think so. We were there at what is supposed to be peak time, and we were actually concerned about how few people seemed to be there – how do all those shops and restaurants stay in business? But ... DC has a LOT of tourists, so again, it may just be a matter of perspective. Also, we were usually away during the day, and in town at night, so the daytime probably was a lot more crowded (though lunch time usually seemed pretty empty too).
Money. As Vagabonda frequently advises, cash rules supreme in Italy! This was somewhat of an issue for us – although hotels and restaurants (even small ones in small towns) all took credit cards, all activities (incl. our driver) had to be paid for in cash and with 4 of us, those costs added up to quite a bit. We changed some money before we left, and notified our bank that we wanted to be able to take more out of the ATM each day. Still, the Italian ATMs seem to limit how much you can withdraw (even if your US bank would allow it) so we could only take a little out from each machine and had to visit several. We spent a fair amount of time looking for ATMs so we could get cash, especially on the second half of our trip when we were in Taormina Mare (there is only one ATM in that part of town that we could find, and it was out of service).
Transportation. We used New Travel Service for all our day trips. They were purely amazing. Always organized and on time, and offered helpful ideas for where good shops and restaurants were in the towns we were visiting, where the public restrooms are, etc. They had large, clean and comfortable cards, and on the days we had Christian himself (the owner), he was particularly funny with his ideas and observations about Sicilian history, life and culture.
With these thoughts, on to the trip.