Flying to Florence (June 2022)

Erin if you use Google and type in Florence and then Akron you’ll find a 14 hour plus flight with two stops.

Either you choose that option or fly to NY or Boston and board direct flights to Florence.

It will be all about time and money.

Is this area your main itinerary? If you plan to visit Venice at all during these 2 weeks, it's usually best to fly into and start Italy trips in Venice- which is also super relaxing and a nice, easy start to a great Italian vacation - , then take the train to Florence. Now, if Venice isn't part of your tour, then certainly begin in Florence - but we usually fly into Venice, Train to Florence with day trips into Tuscany, then fly home from Rome. Florence has a smaller airport and we've just not had as good luck with beginning in Florence, but it's certainly doable. What is your itinerary? Florence is one of our favorite European cities.

Florence has no direct flights to North America. The runway is too short (5200ft) to accommodate anything but short haul regional jets for intra European flights.
The only options to fly to Florence from North America are currently through the following European hubs:
Paris CDG (Air France)
Amsterdam Schipol AMS (KLM)
Frankfurt FRA (Air Dolomiti, a subsidiary of Lufthansa)
Munich MUC (Air Dolomiti, a subsidiary of Lufthansa)
Zurich ZRH (Swiss Air, a subsidiary of Lufthansa)
London is not a good option because British flies from Florence to London City ( LCY) but not Heathrow (LHR) therefore you would need to transfer from LHR to LCY by ground.
Alitalia is folding down next month and I don’t know if the new company ITA will resume flights from Rome to Florence, but Rome to Florence is just as easy by train.

Florence has a pretty small airport, in my opinion you should also look at flights to nearby Pisa. It is very simple to get from Pisa airport to Florence.

Although Pisa has a longer runway and can accommodate larger planes, there are still no direct flights from/to North America since Delta discontinued the direct flight Pisa-JFK a few years ago.
The options to fly to Pisa from other European airports using a traditional airline are even fewer than to Florence. Pisa has lots of flights to many cities, but they are almost exclusively with the low cost carriers (RyanAir, WizzAir, Volotea, Easyjet, Norwegian Shuttle) which do not fly to North America, therefore the connection in Europe would require separate tickets with separate airlines. AirFrance discontinued the flight from Paris, so if you want to fly to Pisa from the US the only viable option would be with Lufthansa/Air Dolomites via Frankfurt, but at that point you could do the same to Florence which actually has more Air Dolomiti flights.
Frankly, considering that you are flying from a State that has no direct flights to Europe and you would need to have two layovers to fly to Florence, I would opt to fly to Rome, then take the train to Florence from the Rome airport. That way you would limit your air journey to one connection only somewhere in North America. Rome has lots of non stop options to North America. Venice has a few non stop from North America as well, but unless Venice is one of your Italian destinations, going to Florence is easier from Rome airport.

Not sure when you are going but I would definitely limit any transfers you need to do within the US. With things being so unpredictable due to Covid you don’t need to be keeping track of entry requirements in different countries. We have flown into Rome and then train to Florence and it is pretty easy.

AirFrance discontinued the flight from Paris, so if you want to fly to
Pisa from the US the only viable option would be with Lufthansa/Air
Dolomites via Frankfurt, but at that point you could do the same to
Florence which actually has more Air Dolomiti flights.

To Pisa, other options are Aer Lingus via Dublin and SAS via Stockholm, Oslo or Copenhagen. But even if Pisa is not that much bigger, it will give you more options. Airline pricing can be very unpredictable, and if Lufthansa's tickets to Florence are way too expensive, the tickets to Pisa might be cheaper.

Milan can also be worth considering as it has a couple of non stops to North America.

I greatly appreciate the help and opinions offered so quickly. Thank you!

We would fly from Cleveland or Canton-Akron. It looks like our best bet will be to fly in/out of Rome and just pop up (via train or plane) to Florence from there.

In terms of an itinerary, during the first 20 days of June, we anticipate:
3-4 nights in Florence
1-2 nights in Assisi
perhaps 1-2 nights in a seaside town that is not CT, and yet to be discovered by us
7 nights in Rome

We would like to relax as well as sightsee and so far are interested in also seeing Orvieto, Norcia... history, art, good food, sunshine and the Saints. Thank you again for your input and sharing from your experience.

In your case flying to Rome is the best option.

Regarding Pisa, SAS flies from Scandinavia (OSL, CPH, ARN) only seasonally starting the very end of June.
Aer Lingus has canceled its flights from Dublin, and I don't know if and when they will be resumed in 2022.
That's why I didn't mention those options.

Pisa is primarily a European low cost airline hub, therefore not a great option from North America with traditional airlines.

Since you are at the airport (probably Rome) I would fly to Florence under an open jaw (multi-city ticket) and return home from Rome. In the end probably cheaper and more convenient than flying into Rome taking a train to Florence.

In terms of an itinerary, during the first 20 days of June, we
anticipate: 3-4 nights in Florence 1-2 nights in Assisi perhaps 1-2
nights in a seaside town that is not CT, and yet to be discovered by
us 7 nights in Rome

We would like to relax as well as sightsee and so far are interested
in also seeing Orvieto, Norcia... history, art, good food, sunshine
and the Saints. Thank you again for your input and sharing from your
experience.

Are you open to car rental, which I think you would need for Norcia? I'm not proposing taking the car to the large cities, but perhaps after Florence, take a train to Orvieto, rent the car from there and do a loop into Umbria. You could also do a seaside stop before returning the car and finishing in Rome (I'm partial to the southern Tuscan coast).

Did you see this recent article? It made me want to go!
https://www.nytimes.com/2021/09/23/travel/castelluccio-di-norcia-italy-travel.html

If you fly into Rome, it’s an easy train ride to Orvieto. We’ve done that as a day trip, and also spent a couple nights in Orvieto and picked up a rental car there.

Diana

You could do a multi-city routing with Lufthansa

CLE-FLR; FCO-CLE

You may want to check that out and calculate the TOTAL travel times and costs vs r/t to Rome and taking trains

A quick check of random dates in June looked like the multi city option would be cost competitive with the alternative(s)