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Drop CinqueTerre OR Siena? Tuscany, Pompeii, Paestum itinerary

Hello kind and experienced folks, I am thinking of dropping either Siena or CinqueTerre from this draft itinerary? What your thoughts?

Italy Itinerary DRAFT (Sep 6–20, or Sep 21 2025)

Flow: Sep 5 Chicago → Sep 6 Florence → Pienza Val d’Orcia → Chianti → Siena ? → Florence → Cinque Terre ? → Naples Herculaneum → Salerno → Pompeii → OR Pompeii → Salerno → Paestum → Rome → Fly home Chicago

We plan to have a car for Florence → Pienza Val d’Orcia → Chianti → Siena → Florence and then do the rest by train.

The detour to Cinque Terre takes time away from visiting Rome so not sure whether to drop it or how to modify the itinerary. I have never been to either Cinque Terre or Siena. I have been to Naples before and I am ok with a day there for food, views, and the Arqueological Museum and as a base for Herculaneum, spending the night at B&B Orsini64 and then on to Pompeii the next day with a night in Naples or Salerno.

We can add a day to this to return home on Sunday Sep 21.
My husband has never been to Italy.
We do plan to return to Italy (Milan area) so perhaps we could leave Cinque Terre for a next trip?

Thanks in advance for your suggestions!
I’m getting there! Phew!

Posted by
12061 posts

Happy to try to help. I get your routing but I am wondering how many nights you plan in each location . Surely you are not sleeping in all of those locations in 2 weeks?

Posted by
12798 posts

You depart Chicago Sept 6 or arrive Florence on Sept 6.?

I am lost on where you plan to sleep and how many nights at each place.

What reservations have you made that cannot be changed without penalty?

Posted by
5 posts

Thanks Laurel. Haha! Apparently, I don’t plan to sleep! Pun not intended but I’m losing sleep over skipping Cinque Terre… or Siena … I know the trains can get us from city to city quickly, but Cinque Terre is the furthest point from our Southern itinerary …

Posted by
5 posts

Thanks Joe32F. My mistake: Sep 6 is arrival in Florence. Nothing has been booked yet! But will book flights this week: Chicago-Florence; Rome-Chicago. I am just seeking input on the itinerary based on car in the wine region and train for the southern part and return to Rome. And Cinque Terre looks “tricky” either way.

Posted by
1095 posts

IMO drop the CT, it’s at least a two night/ three day detour (Florence to CT, 2 overnights in CT to give you a day to visit the villages, CT to Naples) that you can’t really afford time wise. I like the Pompeii, Salerno, Paestum, Rome option mainly because Paestum happens to be one of my favourite sites in Italy! CT would be much better added on to your later trip to Milan area.

Posted by
3408 posts

Since you’ll be visiting Salerno, you could go just a few miles further and be on the Amalfi Coast. Salerno is only 16 miles from the town of Amalfi. You could take the 35-minute ferry between the two and see the Amalfi Coast from the sea.

All the time saved by cutting out the Cinque Terre allows you a few hours to see Amalfi and be back in Salerno by dinner time.

Posted by
3408 posts

Here’s one way to accomplish your itinerary: After seeing Florence, you can take a 75-minute Express bus from Florence to Siena. I would overnight in Siena after having a glass of chianti on the Campo— the place is just magical at night when it’s floodlit.
When I visit Florence, I usually stay in Siena and daytrip into Florence.

Then you could pick up your rental car in Siena — www.AutoEurope.com has car rental agencies in Siena that it brokers cars for at very good rates.
From Siena, drive one hour to Pienza and Val d’Orcia.
The wine town of Montepulciano is only seven miles from Pienza which means it’s a must since you’re already there.
After Tuscany, return the rental car to Siena and then take the bus (2:50) from Siena to Rome.

After Rome, it’s a 70-minute high-speed train ride to Naples. From Naples it’s about one hour to Pompeii on the Circumvesuviana commuter train. Herculaneum is on the way to Pompeii and it offers luggage storage to visitors. Pompeii also has left luggage service at the Pompeii-Scavi train stop.— which also is an entrance to the archaeological park. Since you’re returning to Rome for your return flight, you might see Herculaneum on the way to Salerno and then see Pompeii on the way back to Naples/Rome.

From Pompeii-Scavi, Salerno is a 1:20 train ride.
Paestum is less than one hour by bus/train from Salerno.

Now the fun part— how to allocate the number of nights to your overnight locations! Since you’re dropping Cinque Terre, you actually have plenty of days to enjoy your other destinations at a relaxed pace so you can occasionally experience “La Dolce Far Niente.”

Have a great trip!