Fly into Florence and out of Rome, or into Rome and out of Florence?

I don't think it matters. It might be cheaper to fly in and out of Rome. The train ride to Florence is ~90 minutes, so could be done on a departure day or the night before and stay in an airport hotel if you have morning flight...

Where do you live? What is your home airport?
Flights availability and number of required layovers will make the whole difference.
You can fly to/from Florence only from selected European hubs with limited airlines (basically CDG, FRA, MUC, AMS, ZRH, FCO), whereas Rome FCO is served by many from many cities around the world. As such, also depending on your home airport location, sometimes it is cheaper and more convenient to fly in and out of Rome, and use the train since Rome and Florence are only 90 min apart by fast train.

I will be flying out of Portland, OR. I didn't realize the train trip from Florence would be so short, so I will check flights and see if I could fly in and out of Rome. Didn't realize that was a possibility. That's why these forums (and you guys!) are so great!

Thanks

If you already know that you're looking at specific dates then price them now. Which location seems cheaper for your starting/ending dates? Look at flights. Look at possible hotels. What's the total cost for starting in Rome? For Florence? Are hotels showing availability now? If not, then consider rearranging the itinerary.

Flights are available, and about the same price whether I fly home from Florence or Rome. No need to make the extra train trip this time but I will keep it in mind for future trips.

I will check hotel prices on both ends and see if that makes a difference. There are hotels still available in Florence. I wanted to plan out the whole itinerary before I started making reservations but perhaps if I get moving on that then I could make the trip work the way I prefer. I'm thinking that I will like Florence more than Rome so would prefer to stay just 2 nights in Rome, then go to Siena, Assisi or Orvieto, then end in Florence.

Thank you

I asked about your home airport because that determines if you have non stop flights to the European hubs that have flights to Florence. If your home airport is not connected to those European hubs I mentioned in my previous comment above, flying to/from Florence will entail an extra layover compared to flying to Rome.
In your case PDX has non stop flights to Frankfurt with Condor Airlines and Frankfurt has several daily flights to Florence (with Lufthansa). Otherwise your only chance to fly to/from Florence is with two layovers. If the Frankfurt route doesn’t work for you, then I would rather fly in and out of Rome, if that means one layover only. I hate two layovers.
If you fly in and out of Rome, it’s probably best to go to Florence upon landing in Rome (there is a fast train every 15-30 min). Then I would spend the last few nights in Rome before flying back home. You need to be in the city you fly out from on your last night because flights to North America are generally early in the morning.

I'm thinking I might not mind two layovers. I get restless being stuck in a tiny airplane seat for long periods of time. I like to get off the plane and walk, get food, etc. I do realize the plane is not landing in the middle of the ocean though and one of the legs of the trip will be long no matter what. Maybe best to get it over with?

Is it a hassle to get off the plane in a foreign country? Do you have to go through extra security or anything like that?

"Is it a hassle to get off the plane in a foreign country? Do you have to go through extra security or anything like that?"

That varies with which airport you are coming from, which airport you are changing in, which airport you are going to, and which airlines are involved. I know that's as non-specific as an answer can be, but it's true.

Also remember that customs (control of goods), immigration (passport control) and security are three different things. You may go through one but not the others, at various points. And although in the US people often say "customs" to mean one of the others, in Europe they use the terms correctly. (I saw someone in Dublin ask if he had to go through "customs," be told no, then be confused when he had to go through immigration).

If you specify which airlines and routes you are looking at, people can give you specifics. However, realize that even if the information you are given is accurate at the time you are given it, it can change. For instance, until about two years ago, a flight from the US through Madrid to France did not require going through passport control on arrival in France (only in Spain). Now, there is a second passport control step on arrival in France. So, be prepared to go with the flow. You won't be allowed to skip any necessary steps.

I live on the west coast (my home airports are SFO, OAK, SJC) as well, and I go to Florence every year.
My preference is to fly non stop to a European hub (10-11 hrs flight) then connect to FLR (1.5-2 hr flight). Doing so allows me to be in FLR within 15 hours from take off from California, including one layover time.
Connecting back east in NY or ATL etc. then again at another hub in Europe would prolong my arrival in Florence by many hours.
From PDX you can fly non stop to London Heathrow and Frankfurt.
Frankfurt has several flights to FLR, so you could look into that flight.
Unfortunately no direct flights are available from London Heathrow to Florence, but there are flights from LHR to Bologna and one to Pisa. Both Bologna and Pisa are less than 90 min from Florence. Or you can fly in and out of Rome.
In any case, if you want to get to Italy faster you need to fly the first leg non stop from PDX to Europe, via the Arctic route, without stopping back east.

If the price is the same, I might be inclined to fly into Florence and out of Rome. That said, I did it the opposite way in October-Novemebr 2016. I flew on miles so I think it might have been based on flight schedules from San Francisco. Rome is very intense and you might want to work up to that intensity after you have your travel legs on. But, arriving at FCO and catching the train into town couldn't be easier. A taxi ride to FCO is on the long side, the taxi to Florence is not long and it's cheap at around 25 Euros as I recall. (Now I'm talking myself into saying it's a toss-up). November 1 is All Saints Day and Rome was mobbed with Italian tourists when I was there. I think a lot of people take the whole week off. Otherwise the weather was really nice, in fact quite warm in Rome and I barely had any rain for my entire twelve days on the ground (only significant rainfall was my Vatican day when I was mostly indoors). Your weather experience may differ but I found this time of year was a good time to be there. Siena was also crowded, but I think it might have been on a weekend. Orvieto and Florence not at all. You'll have a great trip, I'm sure.

Having done it both ways, I'd say that a return morning flight is easier and quicker from Florence since it's a smaller airport that is a very quick and not expensive taxi ride from the city center. You won't have to get up at 3:00am. If it's an afternoon or evening flight, leave from whichever city that makes sense for your itinerary.

November is a great time to go!

Thank you all so much for your advice. It sounds like it's not a big deal either way. I think I will go straight from PDX to Frankfurt, and then either Rome or Florence depending on ticket price and arrival time. Ticket prices are about the same right now but they keep changing daily.

Either way it should fine. Thanks again.

Book one ticket. Do not book a separate ticket to Frankfurt and a separate ticket to Rome or Florence.

Sometimes flights into Pisa are less expensive, if you are starting North then going south to Rome.