Italy trip for my Dad’s 80th Birthday - need itinerary help

As I just posted in another thread, I spent 18 days in Sicily last year and it wasn't enough time to see the entire island. Move as much time to Sicily as you can. I urge you to skip Pisa; you'll be sorry you spent half a day on that side-trip when you realize what you're missing in Sicily.

Because Sicily is part of your trip, I'd tend to cut back the stay in Florence a bit, not planning as much day-trip time as would normally be included. Dealing with airports is tiring, and you will need to fly into and out of Sicily. I wouldn't want to do that for just a few days.

I don't know whether it would help your logistics (making Sicily your first or last stop might not work from the airline-schedule perspective), but you can easily get from Rome to Florence or Naples, or vice versa, by train.

IMPORTANT: Where in Sicily was your great grandfather born? Was it in or near Palermo? That would help quite a bit, because Palermo has wonderful sightseeing in terms of churches and oratorios (Monreale, just outside the city, is #1), plus possible side-trips to Cefalu and Trapani/Erice (latter extraordinarily atmospheric). So you get a lot of bang for your buck by making Palermo one of your Sicilian bases. Palermo itself is very hectic, with wild traffic, so it is admittedly not a relaxing city. I can't imagine driving there, so I'd hit the city sights either at the beginning or end of the Sicily leg before or after renting the car.

If I had time for just one other base in Sicily, I'd choose Siracusa. It has the lovely, historic Ortygia district, Greek ruins (including a theatre that occasionally hosts performances), a good museum and some wonderful day-trip possibilities to baroque towns in the interior, including Ragusa, Noto, Modica and Scicli.

The Catania airport has a lot of flights, so it will probably be possible to fly into Palermo and out of Catania, or vice versa. Mt. Etna is fairly near the Catania airport and could be seen just after you arrive or on the day before departure.

In driving from Palermo to Siracusa (or Catania) you'll have an opportunity to stop near Piazza Armerina to see the Roman mosaics at Villa Romana del Casale. It's a very impressive site. Do try to see some of the interior of the island; it's much less touristy than the coastal areas, and the countryside is very nice. Driving conditions outside the big cities generally seemed OK to me (though I was sitting on a bus, not driving), but there are definitely some narrow streets in the small towns, so you must carefully avoid parked cars and shouldn't expect to cover ground rapidly.

I took a short and inexpensive cooking class in Trapani last year. I hope that link is to the right school. We made a hand-formed pasta and Sicilian-style pesto. The teacher prepared a sort of jellied watermelon dessert, and there were some other nibbles set out for us to eat. I learned about the class from a flyer at the Trapani tourist office, I think. Your trip is short, so I think you'll be looking for classes that are only a few hours long. If you don't find something interesting via the internet prior to your trip, ask at the tourist office at each overnight stop.

For Rome, you'll need to make an advance reservation for the Borghese, and the current reports of massive overcrowding lead me to urge you to book a tour of the Sistine Chapel/Vatican Museums that gives you access before they open to the general public. (Don't do this on your first full day in Italy! It means a very early start.) There are multiple companies offering such tours, and the prices do vary, so check before buying.

First, it's great that you're doing this! It should be a wonderful and very memorable trip for everyone.

"I want to keep the price of the flights between locations down by looking at the budget airlines (Ryan Air, Vueling, etc). "

Note that Alitalia has a more generous carry-on allowance as well as one free checked bag, so it can work out cheaper than a budget carrier. For flights within Italy, Alitalia's International website https://www.alitalia.com/en_en/ has the same prices as their Italian website, but has an English language option. Their US website has notably higher prices for the same flights.

Look at Skyscanner to learn all flight options: https://www.skyscanner.com/. While I haven't looked at specifics between Florence and Sicily, Catania is a bigger airport with more flights than Palermo. I do know that Rome has, by far, the most flights from the mainland to Sicily, and Naples is second; Florence will have fewer options, but should still work.

If you fly home out of Pisa, you can spend your last night there, or if the flight is late enough in the day, you can stay in Florence (it's only about 90 minutes from Florence to Pisa's airport, but I do understand not wanting to take chances with missing flights). If you are ending in the Florence area, price flights out of Bologna as well as Pisa and Florence; all three can work from Florence. Or, again, you could spend the last night in Rome and fly home from there. Florence to Rome is only 90 minutes on high speed trains, which are cheap when booked in advance (non-refundable).

If you tell us which airport(s) you can fly from, people can give you more tailored flying advice.

I definitely agree on cutting down Florence by a night or two, and putting the time toward Sicily. I was there 10 nights and ran around a lot, but still just hit some highlights. In case you want ideas (or more about logistics), my VERY detailed trip report is here: https://community.ricksteves.com/travel-forum/trip-reports/sicily-palermo-caltanisetta-siracusa-taormina

The subject of Naples is very divisive. I learned to like it, but others are very put off (even as a New Yorker who found Rome and Palermo not to be difficult or stressful, Naples was a handful). I'm not sure a quick trip there (which is easy to do from Rome) would be pleasant, unless you had specific goals in mind. In his Italy book, Rick does have a recommended day in Naples (Archeology Museum, walk around the center, pizza). If you don't mind a tiring day, this could work; the Archeology Museum was a true highlight for me.

Hi
Before locking in you should consider, going from Rome to Florence, by train, much easier, then return to Rome and off to Sicily. I'd increase the days in Rome, allowing a day trip to Naples, taking them off Florence

Thanks for the advice so far. Very good ideas. I did check out flights on Alitalia and I did notice the luggage allowance which make the price more equal to the budget airlines. I agree that I need to cut off some days from Florence. The only reason really to go to Pisa would be if we were flying out of that city to the US. I will add Bologna to my flight searches. We are flying out of the Washington DC area airports. Dulles (IAD) seems to have the most flights and best prices). I haven't booked the flights yet. Have been tracking some with a non-stop from IAD to Rome and then a flight with one stop from either Florence, Pisa or Palermo back to IAD. Prices are running around $1,550 per person. I don't know if that is good or not. That is booking through the airline (United or Lufthansa) directly. I want to stay away from booking through a 3rd party or online travel agency.

Ideally I can find a reasonable flight where I can go to Rome first, then to Florence by train and then fly to Sicily and then back to USA from there. It just seems that that sequence is a lot higher. But it might be worth the difference to cut out another flight in the trip.

We just got back from a 3 week trip to Italy. Spent six days in Florence. We went to Cinque Terre and Tuscany. Saw the Accademia and Effuzzi. Liked the Effuzzi better. We then took a train to Rome for 3 days. Then took a train to Sorrento(actually Naples then Sorrento). Flew from Naples to Sicily. Flew Voltea. Relatively inexpensive but quick. Spent six days in Sicily. There is a lot to see in Sicily. We stayed east of Palermo.In hind sight if I was doing it again, to cut down some of the traveling time in Sicily,I would stay a few nights in a location and move around closer to where I wanted to go. It made it a long day going from one side of the island to the other by car
.

Thanks Paul for the advice. I agree that to have one lodging base in Sicily makes for more travel time on the road. For me I think it will depend on where we are flying into or out of. I think my best bet personally, based on other posts on the forum, it to either start on the east side of Sicily and work over to the west side (or vice versa) - given that we definitely want to see Palermo.

It looks like there are non-stop flights between Dulles and Rome - maybe from other area airports, I stopped looking when I found one :-). I always prefer that to having to change planes. Of course, prices matter, more so when there are 3 of you, but do consider the ease/comfort/convenience factor. Both Naples and Florence are connected to Rome by high-speed trains that are no longer than 1-1/2 hour rides. It would be easy to fit your itinerary into round-trip Rome flights. Another consideration in choosing flights is that you will have to go through passport control, collect your bags and go through customs when you first land in the U.S. So if you are connecting through, say New York, you have to do that, then recheck your bags and maybe go from the int'l terminal to a domestic one to get back to the DC area.

You will want to fly in and out of Sicily to the mainland. One possibility is booking open-jaw from Dulles to Sicily (changing planes in Rome) and back from Rome. The price is likely to be no more (and possibly less) than booking a separate flight to Sicily. Of course that means starting your holiday in Sicily - maybe not a bad idea to be there a little earlier in the summer. Don't consider doing the reverse, though. If your int'l flight is delayed, there'll be more flights to Sicily that day. But if you fly out of Sicily to FCO and are delayed, you'll probably miss the only flight of the day.

Palermo and Etna are at opposite ends of Sicily. Etna is a day trip from Catania. Best to fly into one end and out other. If you only want to visit those 2 places, then 2 nights Catania, train or bus to Palermo and 3 nights there. If you want to see more of Sicily - and really, you should (so many wonderful sights), you need more time. Then it might be worthwhile to rent a car and traverse the island over another few days.

If Florence is on your list mainly for the Academia, you really could just do it as a long day trip from Rome. That would leave you with time for Naples (Pompeii?) and more time in Sicily.

So I am looking at the following itinerary starting June 7th (probably) based on the advice from this forum (which I truly appreciate). Flying from Dulles (Washington DC area) to Palermo (with a short layover in Munich. 4 Nights in Palermo area and then 3 nights in eastern Sicily with flying from Catania to Rome. Then 4 nights in Rome. Then high speed train to Florence and 5 nights in Florence. I might be able to squeeze in an extra night in any of the locations but it depends on when I book the transatlantic flights and how many snow days my husband's school has used at that point (he is a high school teacher). I know that there are probably much more days needed in Sicily but this trip is to maximize my dad's experience figureing that he will not have an opportunity to return to Italy. Rome, Florence and Sicily were on his "bucket list." The idea for the 5 nights in Florence would be that a day trip to a winery to Tuscany would be included.

Let me know if there are any other ideas regarding this itinerary. I am watching flights and currently find Dulles to Palermo with return from Florence to Dulles (near DC) to run around $1370 per ticket round trip. I am not sure whether to wait and hold out for a better price or to just book and not look back. Further advice would be appreciated!

There was a huge airfare sale this week, check right away! The cheap tickets may be gone (or will be soon).

What a great experience that you will all have together!

Rome: A cooking class that we really enjoyed was cookingclassesinrome with Chef Andrea. I would limit Florence to 3 days and add one of those days to Rome. There's a lot to see in Rome, but it will also be tiring for your dad.

Accomodations: try to pick hotels, etc. that are right in the center of the sites. It won't zap your dad's energy if you're able to be at sites very quickly, and he also would have the opportunity to take a short nap and join you later. Our hotel in Rome was minutes from the Pantheon, and we loved being able to go there in the evenings and enjoy the ambiance.

Definitely skip Cinque Terre this trip.

I'm disappointed in that price, for your sake. I'm not comfortable predicting whether prices for that itinerary are more likely to move up or down.

I looked at round-trips to Rome and flights returning from Milan or Pisa rather than Florence, and still most of the fares were in the same ballpark, though some odd/undesirable routings were cheaper. There have been some great deals recently to Rome, but they were for April and May flights.

I was using flights.google.com for my exploration, and at some point the website advised me that I could save quite a lot by flying out of Newark NJ. There are some sub-$1000 options if you fly in and out of Newark with two stops each way. The price drops about $50 if you can extend the trip until July 2. I think you'll be able to take a look at the connections on Delta.com if you're interested.

As you continue to look at prices, remember that sometimes Milan and Rome are substantially cheaper than Florence, and both are accessible via relatively short train trips from that city. You'd need to spend your last night in the appropriate city, rather than in Florence, however.