Plane or train

Train time from the Fiumicino Aeroporto to Forenze SM Novella takes about 2.5 hours; direct at 13:53 or changing downtown.

Florence to Lecce I would choose an intermediate stop or two to break up the journey.

Tim,

We're going to Lecce from Rome and are taking the train (5.5 hours). I'm 100% in agreement with wanting to avoid the airport experience -- while the flight itself from Rome to Bari or Brindisi is an hour, the whole journey will probably be roughly the same time as the train with WAY more uncertainty and stress, IMO. Plus there are the CO2 considerations (yes we will be flying across the Pond to get there originally, but that doesn't mean we shouldn't do what we can when we're there).

All this said we've never traveled in this part of Italy before, so take my plans with that in mind!

Carrie

Hi,

Taking a fast train from Termini to Florence could indeed be a more convenient option, especially considering the potential challenges of short or long connections for a flight to Florence. With only carry-ons, the train journey provides a hassle-free and efficient means to reach your destination, avoiding potential delays and uncertainties associated with air travel. Additionally, the scenic train ride offers a pleasant travel experience, adding to the overall enjoyment of your journey.
Florence to Lecce: Direct Train vs. Airport Experience

Opting for the 7.5-hour direct train from Florence to Lecce not only eliminates the uncertainties of airport experiences but also allows you to relax and appreciate the scenic beauty of the Italian countryside during your journey. The direct train offers a more straightforward and potentially more enjoyable travel option, especially if you prefer avoiding potential hassles and are interested in taking in the landscapes along the way. Considering the overall travel time and potential scenic views, the direct train could be a more favorable choice.

In both cases, your considerations of convenience, potential delays, and the scenic aspects of train travel appear well-founded. It's always a good idea to prioritize a travel option that aligns with your preferences and offers a more relaxed and enjoyable journey. Safe travels!

Usually people does not understand that Puglia is quite distant from the rest of Italy - Lecce is further east than Vienna and mountains make slow any trip between Tyrrhenian and Adriatic areas. After a lot of experience (when I was a boy my family lived in Bari but we had relatives in Firenze, making the trip by car four to six time per year), I would prefer flying if I had to go to Bari. But you are going to Lecce that has no airport, the closer one is Brindisi. Florence to Brindisi will involve a change in Rome, then add a transfer from Brindisi to Lecce - so it looks that train could be a better choice. If you can go with the direct train it will be long but much easier.

Maybe I’m getting too old but I would try and find the quickest way to get from Chicago to Florence. A 3 1/2 hour train ride coming off an international flight sounds horrid. At least from Milan the fast train ride is 1 hour 40 minutes.

There are options beyond ITA to book an open-jaw with one connection into Florence and non-stop from Rome to Chicago. The single itinerary would be a mix of carriers within a code-share/JV alliance, but it would open more options.

Train time from Milan MXP to Florence is 3:38, from FCO 2.5.

From Chicago to Florence there are only two reasonable ways:
1. Fly non stop to Rome than take the train (2.5 hours including the change at Roma Termini)
2. Fly to Florence via Frankfurt or Munich (with Lufthansa/United). American (Chicago is also an AA hub is not a great option if it involves using London Heathrow since British Airways has only one daily flight to FLR.

From Florence to Lecce, you basically have 3 options:
1. A long train journey via Rome
2. A flight to Bari (non stop) then a shorter train journey.
3. Drive 9 hours on a freeway (plus pit stops)

As lachera said, Puglia is very far from Tuscany (almost 600 miles from Florence to Lecce, more than Chicago to Toronto), and Puglia is also a very long region.

On ITA its either a short connection or long connection for flight to Florence

As you do not mention when this trip would be, I picked random date in April on the ITA site and found the shortest ORD-FCO-FLR stop in Rome is 1hr 45m

I would not see that as 'too short'.

I see they also offer fly/train pkgs.

Thanks everyone with your thoughtful inputs. Many, but not all, of the suggestions I've looked into and still considering.