Hello,
I've finally almost locked down my itinerary with help from all of you. Based on the below, can you please let me know what will be most efficient/best use of my time?
Most specifically, will it make sense to just go straight from Florence to Amalfi or will it help to break out Rome into 2 segments as shown below.
My flight in/out dates are fixed from Florence/Rome, everything else is still flexible. Any other feedback is appreciated! Thank you!

Option 1
9/8 (land 6pm) to 9/12- Florence (including a daytrip to San Gimignano)
9/12 (arrive early afternoon by train) to 9/14 - Rome
9/14 (arrive early afternoon by train) to 9/16 - Amalfi coast (staying in Positano tbd, flexible)*
*Train to Naples; transfer to Sorrento; use car service to hotel
9/16 (arrive early evening by train) to 9/20 (flight 7am)- Rome

Option 2
9/8 (land 6pm) to 9/12- Florence (including a daytrip to San Gimignano)
9/12 (arrive afternoon) to 9/15- Amalfi coast (staying in Positano tbd, flexible)* Train to Naples transfer to Sorrento; use car service to hotel (unless there's a faster option)
9/15 (arrive afternoon by train) - 9/20 (7am flight)- Rome

I think 3 nights in Florence, 2 nights in Rome and finish your trip on the Almalfi Coast. Can you fly out of Naples or spend your last night back in Rome.

I recommend Hotel Adriano in the Pantheon area. You are with in walking distance to most sights. I loved Rome and all the historic sights.

Florence is fabulous!

We are taking our first trip to the Almalfi Coast in September.

Good Luck and enjoy your trip!

I like option two- less checking in and out of hotels.

Have you looked at taking the train from Florence to Salerno and then either a bus or boat (my preference) to Positano? I think it would be easier and less expensive ( no car service) than your current plan. It's probably faster too.

I'm in agreement with zoecat. Going to Rome twice doesn't really make sense. And the train from Florence to Salerno, and then the boat to Positano, is a wonderful option.

Another vote for option 2. Gives you more time actually enjoying Italy, rather than traveling.

Another vote for option 2. But I am curious, why is option 1 even in contention at all? If by train, Florence to Napoli is only a 2 hrs 51 min ride. You cam compute easily that option 1 costs more because you have to pay to do extra Termini-hotel-Termini trip, as well as time to do these.

Option 1 has 3 full days in Florence, 1+3=4 full days in Rome, 1 full days in Amalfi coast, and 5 partial days.

Option 2 has 3 full days in Florence, 4 full days in Rome, 2 full day in Amalfi coast, and 4 partial days.

Notice that the option 2 gains one full day in Amalfi coast without taking away hardly, if any, time from Rome.

Ah thanks everyone! At first it seemed like train from Florence to Amalfi will just be such a long day but I decided to use Sorrento as a base so train from Florence to Naples then Sorrento doesn't seem so bad.

Ok nevermind, it looks like Florence to Salerno then Ferry ride to Positano is not as long as I thought...I will go with that. Thanks again!