Thoughts on Itinerary for 2 weeks Venice/Florence/Amalfi Coast/Rome

Hi MissHaley! Welcome to the forums!

Can I back up a little? This concerns me a bit:
3) 3 nights outside Florence
a. Wedding
b. Florence Museums
c. Possibly Pisa or Tuscany Vineyard(s)

Where exactly "outside Florence" will you be staying? Do you know how you're going to get there? I'm asking as locations in the countryside aren't always accessible via public transit...which would affect your sightseeing plan for B and C. That brings me to your "B" day: one day is very little time for a city FULL of wonderful museums. Trying to cram them into a single day is asking for serious museum burnout! Also, the State Museums (Uffizi, Accademia, etc) are closed on Mondays so if your single day just happened to fall on THAT one....

Editing to add, just in case you didn't know: Certain of Florence's museums also require advance, timed-entry reservations. Apologies if this is not new info to you. :O)

Honestly? I'd scrap the Tuscan vineyards/Pisa idea and opt for a 2nd day in Florence. You can drink wine in there too. :O) You could also steal a day from Rome: 4 nights/3.5 days is a minimally OK intro to the Eternal City.

Day "A": looks like you're planning to travel the same day as the wedding? Is it in the evening?
Sorry this doesn't answer your Naples/Sorrento/Amalfi Coast question but we'll get it, promise!

I count trips in nights, but for example you say three nights outside Florence. That would mean two full days--one for the wedding, so on the other full day you would have time to explore Florence or do a day trip, but not both. You would have a little time on arrival day.
It is a bit rushed, but I actually think you are okay with your Naples/Amalfi coast plans. The day you arrive, you could explore the archaeology museum and do some kind of tour or grab pizza that evening or the next morning before departing. And while in Sorrento, one full day for Capri and one full day for the Amalfi coast. Since you are seeing Pompeii the day you depart, it looks like it will all work out.

Rather than devoting an Amalfi Coast day to a boat trip, I recommend a diy or private guide land trip. If I’m remembering correctly, RS has recommendations for driver/guides, which would be more efficient (though lots more expensive) than the buses.

Positano is the least interesting among the three main towns. It is full of tourist-oriented shops and little else. My advice is to skip it and visit Amalfi and Ravello, instead.
Amalfi has a pretty cathedral, with a small museum. Ravello has two beautiful villas, one with a gorgeous garden and stunning views of the coast. The coast is much better seen from above than down at sea level.

Kathy, Thanks for the questions around Florence... Here are additional details that hopefully make more sense... maybe?? lol ... the plan in Florence is:
Day A - Arrive on the AM train from Venice, store our luggage, spend the rest of the day sightseeing, then pre-arrange private driver out to the venue (about a 45 min drive outside of the city).
Day B - is Wedding Day. It is an evening wedding, so considering a short trip out to a vineyard or (Possibly Pisa if enough time) via private driver.
Day C - The wedding party has already pre-arranged a shuttle to take guests into Florence for the day and then back to the venue.
Day E. - AM Shuttle to Florence train station (not sure yet if the wedding is providing this for guests, if not then will arrange private driver) then on to Naples.
None of the days in Florence are on a Monday :-), and I am aware that museums need advance ticketing and timed entries, but thanks for the heads up! :-).
Rosalyn, Thanks for the suggestions on Positano vs Amalfi and Ravello... I think we are going to stick with a boat trip rather than traveling the road from Sorrento. While I have navigated white knuckle drives before (like downtown New Dehli in a TukTuk :-O) I want this trip to be relaxing. I will look for a boat trip that includes Amalfi and Ravello...

ALSO: If y'all had the choice... would you stay in Naples (I can stay on Marriott points) or in Sorrento to day trip out of?
Thanks Bunches!

It seems right to have a night in Naples and a few nights in Sorrento given what you have laid out, but if you wanted one base, you can get to Capri from Naples, and you can take a train to Salerno and hop on the ferry to the AC. I'd also much rather see the coast from a boat, with stops in a village or two of course.
You will find fairly strong opinions about Naples vs. Sorrento here--they are quite different, so it just depends on what you are after, but splitting the stay does give you a bit of both.

Thanks for the additional details, Haley. :O)
Naples or Sorrento to day-trip out of? Sorrento, hands down.
Oh, and you don't need an 'organized' boat trip to Amalfi and Ravello. Just use the ferries + a good guidebook.
Capri is not difficult to do on one's own either (we have.)

This tour (Mondo shared tour's Pompeii Walk) of Pompeii has been highly rated amongst RS posters whom have done it, although I don't personally think 2 hours is enough time. You don't HAVE to leave when the tour is over, though; just don't go outside the security area and continue to explore on your own with a guidebook.

https://www.sharedtours.com

IMO one night in Naples would be a big mistake. Add a night to Sorrento and do a day trip, the commuter train to the Garibaldi station [downstairs at Napoli Centrale] taking an hour:

https://www.sorrentoinsider.com/en/naples-to-sorrento-train-schedule

Note Pompeii Scavi is the stop for Pompeii.

This is not to say that the train is convenient, but you could visit Pompeii on the way to Sorrento; there is a luggage drop.

If planning on a driver to take you to your Sorrento hotel, arrange to be picked up at Napoli Afragola.