Flying in/out Florence, Rome Pompeii, Calabria

Allison, I think first you have to map out your interests as this will determine the perfect itinerary. Depending on where you fly in & out will play a huge factor in your intinerary. You left out a favorite city of mine, Venice, which is absolutely magical!

I'm traveling with 12 others and we thought Venice may be for another time. I've been and I agree that it is indeed magical!

Interests:
Rome: the ancient ruins and St. Peter's Basillica
Florence: I felt like there was just too much wonderful art to skip it! Staying in the Tuscan countryside is very appealing...going in to the city for day trips
Pompeii: I've heard that there is a town very close by that has incredibly preserved remains of the vesuvius eruption
Calabria: hometown of my aunt's late husband..she wants to go for sentimental reasons.
Thoughts??

For your desired itinerary, flying in and out of Rome makes the most sense. Calabria isn't a typical tourist destination, so I assume you're including it for other reasons and that it will be an important part of your trip. It's a long train trip, so it might be efficient to fly directly from Rome to Reggio Calabria and take a train or rent a car to your final destination. You could then work your way north to Pompeii (maybe stay in Sorrento), then Florence and finally Rome. For a 10 day trip, you should drop either Calabria or Florence. For a 14 day trip, the 4 stops are doable even with the long travel distance from Calabria. Start by planning 3 days for each destination and 1-2 days of travel time (2 if including Calabria), and then refine your itinerary based on everyone's interests.

You might consider that some of the smaller airports do not have flights in and out from the U.S.A. Florence is one. Pisa does have Delta flying in and out from JFK. The big internationals in Italy are Venice, Milan and Rome.

If you don't mind connecting somewhere in the EU or Switzerland, you can fly into and out of most any airport you wish. When we went two years ago, we wanted to fly into Florence from California. We did exactly that and it was quite nice and uneventful. However, we had to connect via Frankfurt.

I've never been to Calabria so I can't comment on that but this is what I would do:
Probably fly in and out of Rome but this means backtracking. Florence for 3-4 nights (maybe day trip to Sienna), Rome for 4 night (get RS's recommended tour guide Fransesca Caruso to see the sights with, she is fabulous!!!), Sorrento for 3-4 nights, from here you can do a day trip to Pompeii and see the beautiful Amalfi coast.

Flying in and out of Rome is usually the least expensive (and there are nonstop flights!) so, unless you have found an airfare sale to Florence or Pisa, I'd fly into Rome. How dead set are you on Florence? If you are interested in Rome, Pompeii, Calabira, etc., that would be the place I would save for another trip...but it is easy to get to by train from Rome, so do-able if you want. I would head to Florence first probably and make my way down...and get a local flight from Lamezia Terme to catch your flight back to Rome (I guess you could do it the other way too though...or even head straight down to Tropea by train and then up) There are places in Calabria that are VERY touristy...like Tropea (and that whole coastal area actually)...you can get there by train...and there are inland spots that are difficult to reach by car and you would need to know the local bus lines and schedules to be able to travel there - if you plan on exploring your heritage (and your family is not from the coastal area), it will be difficult without a car. With a tight time-frame, I'd base myself in Naples for the Pompeii excursion - I know some love Sorrento...but it would add extra travel time and excursions along the coast from Naples are terrific as well....or even Salerno if the train times work better for heading to Southern Italy (I don't know the schedules - check on the trenitalia site) Good luck with the planning!