Trains in Italy

Once you are in Italy any of those towns are easily accessible by train. I'm not certain about Assisi, but the others are connected by high speed rail (Assisi you may need to take a slower train). Booked in advance, fares are dirt cheap compared to flying and city-to-city travel is city center to city center (booked in advance high-speed quiet-zone business class from Bologna to Naples: 49.70€). I flew into Florence last September and simply took the tram into the city proper, getting off just a few blocks walk to my hotel. When I left Rome, I had a one-block walk to the metro, got off at Rome Termini and took a direct train to the airport.

Suggest going Venice to Florence to Assisi to Rome.

Venice airport into town can be handled a number of ways. My preferred is to take the bus from the airport door to Piazale Roma in Venice, then by vaporetto tothe closest stop to your hotel. Then vaporetto back to the train station and get a high speed train to Florence. Buy this in advance as they are like airline tickets, seat reservation required and prices at max when bought last minute. There are 2 companies that run this route, Trenitalia and Italo Treno. Take your pick.

Florence to Assisi is by regional train. Always the same price and no reservations. Same applies to Assisi to Rome.

Remember to pack light if you want to travel easily.

To get from Florence to Assisi is a little complicated.

You'd catch a train down to the Terontola Cortona train station. There you'd catch a 45 minute bus to the Perugia train station. There you'd switch to a short tram ride to Scale Mobili - Pincetto - Minimetrò (6 minutes and 3 stops).

It's easier to get there from Rome, but there's no reason to go that far south and then double back north. It's just a little hassle to get there from Florence.

When checking Italian train websites remember to use the Italian names - Roma, Firenze etc. Rick’s Italian guides have all sorts of useful info on using the trains in Italy. I have traveled solo and found the trains easy to use.

For hotels a lot of us on the forum use a site like Booking.com to find info on hotels butt then book directly with the hotel. One reason is that on Booking.com iit will say no availability but if you go to the hotels’ web site there is availability and often a better rate. Booking.con is good for hotel reviews as well.

Transport between airports and city centres is straight forward in Rome, I would use taxi, it’s a set rate. Or arrange to be met by a driver; Rome Cab is recommended, cost is on a par with taxi. There is also a train but you will need to get from the station in Rome to your hotel, so for two of you taxi or car is probably the easiest.

Google Florence to Assisi and you will find info in day trips, unless you plan on staying in Assisi this might be the way to go.

Good luck with your planning.

You'd catch a train down to the Terontola Cortona train station. There you'd catch a 45 minute bus to the Perugia train station. There you'd switch to a short tram ride to Scale Mobili - Pincetto - Minimetrò (6 minutes and 3 stops).

I'd rather take the Tram from Florence to the Villa Costanza parking, then the Flixbus direct bus to the Assisi suburb of Santa Maria degli Angeli.

The Flixbus bus departs at 6:15, 13:35 and 17:25.

Thank you all for the responses. I am printing everything out that you said to help me plan. I'm still nervous!

I did some googling and it showed that Rail Europe does have a direct train from Florence SMN station to Assisi. Is this accurate or something I am missing since Trenitalia and Italo were the ones suggested to use?

Rail Europe does not run any trains. It is simply a ticket reseller, like Expedia or booking.com or other similar sites.

Rail Europe does have a direct train from Florence SMN station to Assisi.

RailEurope is a reseller (with an awful reputation). They do not run any train. There are 7 direct trains each day between Florence and Assisi, the first departs at 8:02, the last one at 21:52.

On trenitalia.com, if you want to see only direct trains between two cities, make a search and click the "Back to search" button. Then turn on the "without changes" toggle button.

Only buy Italian train tickets from Italo or Trenitalia.
There are websites and apps for both.
You can get a direct train from Florence to Assisi , then a short 8 minute bus ride up to the main part of the town.
It takes around 3 hours, and it’s not in the least complicated!
No need to be backtracking around with multiple stops!?

Our family of 4 travelled to Italy for the first time last year. We found the trains in Italy easy to use and our purchase ran the gamut from booking online, to in person with a clerk at the desk, to using a machine.

You might start with this article from this very website https://www.ricksteves.com/travel-tips/transportation/trains/italy-rail-passes. However, ignore the advice about passes in Italy. Rail Europe is a ripoff versus buying point to point tickets. Always buy from the train company website (Trenitalia or Italy) in advance for the high speed trains, I.e., Venice to Florence. Advance tickets are available at a discount but must be used on the specific train booked, much like an airline ticket. Local trains (called Regionale) can be purchased at the station before travel. These will serve you from Florence to Assisi and Assisi to Rome.

I know it seems scary when you’ve never done it, but it is as simple as buying tickets, getting to the station 20 or 30 minutes before your train, finding the right platform, and getting on board. Pay attention to the stop you want and get ready to get off a few minutes before the train arrives if it is not the last stop. If you buy a Regionale ticket at the station, be sure to validate it before boarding.

Spend some time on the site www.Trenitalia.com looking up schedules and prices so you see how discounts and advance purchases work for the high speed frecce trains. You may not be able to see the dates you need this early as there are schedule changes (usually minor) in early June, but you’ll get a feel for it.

There is also a direct Siena - Assisi bus, it's run by Flixbus,

Also look at the site called The Man in Seat 61.
Not for booking, but to get an idea of how the train systems work in Italy.
It's very easy once you've taken your first train and figured it out!
I look forward to my train travels every time I go to Italy.

The Man in Seat 61 is an excellent resource. We traveled from Rome to Venice on the train (i live in Southern California where we all have cars and no one knows how to ride a train) and it's not hard to buy your tickets from the machines at the stations. We stayed in Padua and took a regional train to Venice for 5 EU. The regional trains are slower, with more stops, but are very budget friendly.

Don't be nervous!

My sister who hadn't been overseas since the late 1980s did a mother-daughter trip with her 24 year old over Christmas/New Year 2020 with a very similar itinerary to yours and they had no problems at all travelling around by trains. I think my 24 year old niece did most of the logistics; in most of the photos my sister is just sipping Prosecco and looking at sunsets.