Help with Italy Itinerary for 27 Days

Looks like a good plan. Palermo driving and parking are a nightmare so you might want to spend a couple of nights somewhere easier like Trapani. Great food and close to Segesta, Mondale doable from there. You can go to Cefalu by train, FYI.

Day trip from Florence: Lucca!

Hey! Wow, what a great trip.

I’ve been to Sicily twice - once by myself, once on a Rick Steves tour. I would do a day trip by train to Cefalu. Picking up the car when leaving Palermo, you could easily visit Monreale and Segesta on your way to Trapani and day trip to Erice. 1 or maybe be 2 nights in Agrigento Is fine. Consider a night in the small town of Piazza Armerina and then a night in the hilltop town of Ragusa. On your way to Siracusa (stay on the island of Ortigia) you should stop in Modica and Scicli.

Taormina is a summer resort so in early October it should be pretty well shut down. I’d only drive there from Siracusa for a short visit and then drive to Catania. I had a great time visiting the city itself (fish market, WWII museum) on one day and I drove up Mt. Etna the next and then circumnavigated the volcano, stopping in a few small towns along the way.

From Bologna, Ravenna with its renowned mosaics should be on the top of your list. Pisa, Lucca and San Gimignano are all good day trips from Florence. On your way back to Rome, consider an overnight in Orvieto.

In my opinion, Monreale is the top choice of your first group of options. You can do it by bus, I think, from Palermo. You can also get to Cefalu from Palermo by train. A day for each one is sufficient.

As I recall, we stopped at Segesta on our way from Palermo to Agrigento. An hour or two there is also ample time.
Montefalco and Spello are easily combined in a single day trip.

Buon viaggio. I hope you get to go.

Looks like a fun trip. I spent 2 weeks in Sicily this past Summer (into Palermo and out Catania like your trip).

1. Palermo--as it has been already mentioned, don't get a car in Palermo until you are leaving and even better if you take the shuttle back to the airport it is an easy jump onto the freeway from here. Do Monreale by bus, small crowded roads leading to Monreale and around the cathedral. Also take the train to Cefulu, easy peasy. By car, Segesta is easy stop just off the interstate about an hour from Palermo. Only good for 2-3 hours, besides the temple and amphitheatre nothing else but beautiful countryside. Could swing by here and Corleone on your way out of Palermo depending on your direction for the night. (I went to Erice for one night, great for one evening wondering the old fortress and city walls).

Agrigento is a wonderful site filled with many temples and ruins. The arch. park is about 3-4 kilometers below the old city of Agrigento. When you leave here heading for Siracuse, make time to stop at Villa Romana Casale outside Pizza Armerina. Wonderful old pallazo from Roman times. Then maybe spend the night in transit at Modica or Raguza.

When you get to Siracuse, driving was pretty easy. Road along/near coast with signs for Ortigia. (You'll want to stay on Ortigia, fantastic area for restaurants, peaceful, etc.) Upon, crossing the bridge onto Ortigia there are signs for a parking garage on the north side of the island.
Driving into Taormina is kind of difficult. Parking outside on either end of town or stay in one of the hotels clinging to the hillside just below town.
Catania was fairly easy to navigate and return car at airport.

Bologna is close to Ravenna with the incredible mosaics in the churches or a day trip to Verona and tour the arena and old town.
From Florence, most people head to Lucca or Siena. Both wonderful towns that I have stayed for days and still feel the need to go back.
Enjoy!

About Bologna and Emilia-Romagna:
Bologna is very nice and worth a ful day to be visited. I mean the historical center and the most important museums/monuments. This city is even an important train hub, so you can find connections to everywhere.
In Emilia-Romagna there are several nice cities and towns to be visited.Three of them are UNESCO World Heritage: Modena (for Romanesque Cathedral and the main square), Ferrara (for Renaissance fortress and other palaces) and Ravenna (for Bizantine mosaics). On top even Parma is a very nice city with a lot of monuments. All this 4 cities worth a full day to be visited, so you can choice one or too depending by your interests.

I certainly agree with the suggestions of not having a rental car in Palermo. Pick it up on your way out. Palermo is very walkable or you can arrange for a private driver to get to sites further out. That will save you time and frustration. There is also a free shuttle bus in the city although I have never used it. This past September I spent a week in Palermo as part of a 22 day trip around the island of Sicily. It was still very hot in September. It was my second trip to Sicily and there were so many places that still I did not get to see. We used Palermo as our longest base, staying there six nights. I suggest a visit to the Regional Archeological Museum Antonio Salinas. When choosing daytrips from Palermo, you have so many great choices. Monreale is quite close by and the mosaics in the church and cloisters are beautiful. The catacombs are on the way towards Monreale. I was somewhat leery of going there but they were ok. I enjoyed a visit to the Sanctuary of Santa Rosalia in Monte Pellegrino. Cefalu is a longer day trip. Take the train. The train station is an easy walk into the historical waterfront area. It is a great town for strolling around and the area is quite compact. If you do have a car you might combine Cefalu with a visit to one of the Madonie towns or Caccamo. If you decide on a visit to Segesta and you have a car combine it with a visit to Erice and Trapani. Speaking of ruins you said you are going to Agrigento. On this past trip I went to Agrigento and Selinunte. Both were beautiful, both have lots of ruins, but I actually preferred Selinunte over Agrigento. Agrigento, in September, was absolutely packed with people, all vying for that perfect photo. Selinunte, which is an extensive site right on the waterfront, was nearly empty. We stayed two nights in the town of Mazara del Vallo and visited nearby Selinunte by public transportation (a short train ride and then a bus) as a daytrip. Mazara del Vallo was an unexpected gem of a town. I saw it featured in the youtube series titled “Sicily Unpacked. One of my favorite places on the whole trip! I highly recommend that you view that video before your trip. It will give you lots of great ideas. It was recommended to me by one of the Forum regulars when I was planning my trip.
As far as suggestions for daytrips out of Bologna, I very much enjoyed Ferrara.

Thank you all for your suggestions and advices. My husband and I will be taking all of this into consideration if and when we make this trip. This forum is wonderful!

Can't comment on your Sicily portion, never been there.

Your plans for Umbria (staying in Assisi) interest me, since we plan to spent a week in Umbria, using Perugia as our base. We plan to take the train to visit Spoleto, Assisi, Spello, and more. Parking can be an issue, so we won't be renting a car.

As for Bologna, been there, it was OK, but we weren't wowed. Still, don't miss Ravenna

From Florence, Siena is a great day trip. Pisa and Lucca are must see places, but you probably don't want to try them both on a day trip.

Car rentals are not available in Assisi; when there last year we rented our car in Perugia. While staying in Assisi we took day trips to all on your list except for Spoleto. Gubbio was a pleasant, low-key day--be sure to take the "bird cage" lift UP, then visit the Sant'Ubaldo basilica and the surrounding grounds. There is a pleasant bar/cafe nearby with incredible views (and a pretty tasty Spritz:)!). Then you can walk back down to town on a well-maintained trail with interesting stops along the way. My other recommendation is Spello, both the old town and the Villa of Mosaics. You can pair Spello and Montefalco.

I agree with the recommendations to day trip from Bologna to Ravenna. It will be a very full day, but you won't regret it! While in Bologna, you might be interested in the walking tour offered through the Tourist Information office on Piazza Maggiore; it was both informative and entertaining. The Bologna Welcome website can provide you with excellent suggestions for your time in Bologna.

Hi there,

About Florence and beyond, Day trip to Cinque Terre worth the money and time. Also you can opt for San Gimignano and Siena, you can't do both is the same day. Or we did just a private wine tour with this company https://www.florencewinetour.com/
Pay attention on traffic limit area in Florence ZTL, whole city is cover by gates where if you pass rent a car company will mail you the fine of 98 Euro each time you pass through this "entrance".