Trip Planning Help for Parents 50th Wedding Anniversary July 2019

I have stayed in Florence but only visited the city itself while there.I ave stayed in Tuscan villages many times and did a day trip to Florence once. I wish you had more time for Tuscany. I have never combined Tuscany with Amalfi/Sorrento
but understand you will be in Calabria already. I would take time from Sorrento to add to Tuscan countryside. Stay in a place with a pool in Tuscany. Your son will love it after touring during all day.
You should rent a car in Tuscany, drop it off in Chiusi or Orvieto and take train to Rome, or easier, drop car off at Rome FCO, take taxi into the city to your hotel. Or rent the car at Naples airport and drive north to Florence or more rural Tuscany. Excellent highways, similar to interstates. It will be so much easier than taking the train with five passengers and luggage. Congratulations to your parents on their 50th anniversary.

For sure upon landing and connectingto fly to calabria then stay 1 day u will be exhausted , then after 1 day travel to Sorrento. Slow down abit. Stay in florence at least 3 days then daytrip to one tuscan town like Siena, very easy.
Remainder could be or Rome.
Sorrento and AMalfi area should not be missed for sure.
Book lodging early by January ,as u are going peak season and need multiple rooms. U did not say your budget but realize ac is not a given.

First of all, congratulations to your parents on 50 years! My husband and I are on #49 this year, and we are 72 years old and in good health but slowing down. Having read your itinerary, I am wondering if it will be too exhausting for them. We were in Italy this past May,, and we went to 4 places, spending about 4 nights at each place. We found that traveling days took a lot out of us. I understand that you are trying to make this a special trip, but there are 3 generations traveling, all with different levels of energy! Have your parents traveled to Europe before? Do they know their stamina level for this experience? Maybe it would be a good idea to review this itinerary with them to get their input.

If at all possible, add a day to your stop in Amentea. I'm close to the same age as your parents. To have 2 travel days with only 1 in between
would leave me exhausted, and I'm very active. Give them an extra day to recover.

I have traveled into Rome or Naples for the last 15 years as my daughter lives just north of Naples. I've also had the luxury of most of them being a month long.

If you can't find a private driver, there's a bus that connects SUF with the train station, takes under 5 minutes. Then a train to Amentea about an hour.

I'd probably rent a car for a day or two, since you plan on going to Fognana Castello.

Edit: it's a beautiful area, if you decide to drive, drop the car in Salerno and ferry from there.

For the trip to Sorrento, try to take the 8:00 train to Salerno, just under 2 hours, then the ferry to Sorrento, 1hr 45 m. Note, you will have to switch ferrys in Amalfi but this combo is your fastest transportation to Sorrento.

If your parents have not been to Florence, are interested in art and beautiful architecture, spend 2days there. Remember the city sits in a river valley, so if it's hot it can be miserably so. Make sure your lodging has AC. There are several easy day trips from the city by both bus and train, you just have to decide if leaving is worth the lodging change and car rental. If you stay, you then have easy rail access to Rome.