Itinerary

Good, you have the big three, Venice, Florence and Rome.
Not sure how many days for your trip or for each location.

I don't suggest that you do a day trip to Pompeii/Amalfi. You need 3-4 days to do the Naples area right. If you do go, you will have a hard time visiting Pompeii and the Amalfi coast in the same day, especially with all the travel time from Rome.

You should plan on visiting Pompeii, Sorrento, Capri and the Amalfi Coast.

You will need 2-3 days in Venice, 3-4 in Florence and 5-6 in Rome. One more day in Florence if you do a day trip to Sienna.

Good stuff, thanks. Yep, we're a long way from knowing days, but this helps, major. Sounds like the itinerary is doable? Specifically, there's decent train service between all points, correct?

Frequent (like hourly or more) high speed train service by 2 companies, Trenitalia and Italotreno.

Save places south of Rome for a separate, future trip.

Hey there, Brian - welcome to the RS forums!
Sure, your plan looks doable as long as you give it enough time. Pompeii/Amalfi coast? Can be done in a (looooong) day but I don't recommend it. The Naples/Sorrentine/Amalfi regions deserve the lion's share of a week so I'd save it for a separate trip, if at all possible.

The other issue with trying to do Pompeii AND Amalfi Coast in a day is the amount of time you have to spend sitting on transport. Doing JUST Pompeii would help but I sure wouldn't short your time in Rome to do it, depending on how much time you have to devote to the Eternal City, unless you've a keen interest. For Rome alone, I usually recommend a minimum of 4 nights/3.5 days. That missing 1/2 day would be your time transiting from Florence; subtract a 1/2 day for any other relocations from one city to another.

Rome (Fiumicino) would be a good airport to fly home from.
As Sam said, all 4 of your main locations have rail service. Siena does too although a lot of folks prefer bus service to that one; it gets you closer to the center of the city than the train station. You can get to Pompeii via a combo of "fast " train to Naples and Circumvesuviana commuter rail to the station right in front of the main entrance to the ruins. This is a good overview on how to get there.

https://www.seat61.com/places-of-interest/day-trip-to-pompeii.htm

What season are you planning your trip for? It can make a difference in how soon you want to put the giddiyup on for booking hotels, and there will be attractions that require advance reservations too.

Hello brian.westbye, and welcome to the boards,

With the exception of Fano this sounds like many first trips to Italy - Venice, Florence, Rome are called the "big 3" for a reason. Fly into Venice and out of Rome and train everywhere in between.

I would recommend two weeks for a trip like this - depending on how long you intend to visit family in Fano. Add an extra night in your landing city because you'll effectively lose at least part of a day to jetlag and culture shock - I'd say 4, 5, 5 nights with 14 days and then add nights for Fano. If you can spend more time that's great but I'd start on a schedule in this range and adjust.

Fano is on the eastern coast so you could do Venice > Fano > Florence and not back track through Florence but it's a difference of a few hours on the train so it's not crucial.

List what you want to see in each city, decide what you have time for and book tickets for must see things once you have dates. Siena is a great break from the big cities and can be easily visited by bus or train. Pompeii is a really long day trip from Rome so I would consider Ostia Antica for an easy day trip (less than an hour) out of the city with at least some of that 'lost city' experience instead.

Sounds like you're on track, keep planning and have a great trip,
=Tod

The Amalfi Coast is a victim of its Instagram success- it's very crowded three seasons of the year, and shoulder season is no longer less traveled. Compound that with poor infrastructure, narrow roads, traffic congestion, and poor public transportation. There is no quick and efficient mode of travel, it's very different from areas north of Naples. The Circumvesuviana train doesn't always run on time, is pretty gritty, with no air conditioning. You need lots of patience- and time- to explore the area.
Safe travels.

I think Fano might fit better after Venice.
Train means change in Bologna either from Venice or Florence but from Venice to Fano then to Florence is a bit less time and I believe fewer changes.

Rome2rio.com is a fun tool- you can play around on it to see what your transportation options are but always go to the actual train site to confirm and purchase tickets.

Trenitalia- fast trains and regional trains - also has easy to use app-
https://www.trenitalia.com/content/tcom/en.html

Or ItaloTreno- fast trains only ( does not service Fano) also has an app
https://www.italotreno.it/en

I’d suggest a couple overnights in at least one smaller touristic town as a change of flavor; something like Lucca or some Tuscan hill town/agriturismo. Overnight in Siena doesn’t suck either.

There are no trains to the Amalfi Coast towns. Your last transportation leg would be via ferry, bus or private car. The nearest rail stations are in Sorrento or other points along the southern end of the Circumvesuviana route or Salerno (on the main rail line). I wouldn't recommend visiting Pompeii from Rome, but it can be done if you're satisfied with a 2- to 3-hour visit of the massive site and are up for a long, tiring day.

The Amalfi Coast takes longer to reach and has several towns people want to see, so there just aren't enough hours in the day for a reasonable visit there. To see the Amalfi Coast I'd want to base either somewhere on the peninsula (note that Sorrento isn't on the Amalfi Coast, though it is a very popular option) or in Salerno.

Thank you all so much! It's all starting to come together!