Hi Tyler,

my first comment is that if you are going to travel in October/November, you might like to rethink going to the Amalfi, as by then, I gather, it has more or less shut up shop. you might substitute Puglia or Siciiy. but not only will weather probably be better in May then in oct/november, but the days will be longer too.

the next consideration, is where to fly into and out of. Venice is very popular as an arrival airport - arriving in the city by water is seen as very romantic [by some!] and venice makes a pleasant and traffic free introduction to Italy.

were you going to the Amalfi, i might go there next, then Florence, the CT, and Rome. [there's no simple way to get easily from one to the other unless you go strictly from north to south, and even then it's difficult to know where to fit in the CT].

why end in Rome? once you've been there, everything else will seem tame!

Working north to south in November would put you on the Amalfi Coast at a very quiet time. Some hotels and a few restaurants will have closed for the season and public trans will be on reduced schedules. Possible bad weather could prevent your being able to get to Capri and overall negatively impact your enjoyment of the area. Or not. There's no way to predict/guarantee the weather. You could improve your chances a tiny bit by heading to the AC after Tuscany and ending the trip in Rome, but public trans schedules would still be reduced.

But have you checked your flight options into and out of various cities in May and October/November (this year, anyway)? That might have some bearing on the order. For us, departing Venice for home almost always involves a painfully early departure and from Naples the connections don't always work very well.

FWIW, we usually travel in mid- to late-October. Some years have been better than others, but we've generally had very good weather on many trips to Italy at that time.

May for sure!
Longer days, better weather, and spring flowers.

Tyler, I agree with May. Assuming you are traveling using public transport, consider this flow. North to South. Venice, train to CT (at least to Rapallo just nort of CT)apx 5.5 hrs Freciabianca (express) train, one change in Milan. CT to Florence (Tuscany) by train, many choices with train change either in Pisa or La Spezia. Florence to Rome, again many train options (express) apx 1.5 hours. Train to Amalfi. This would require a back track to Rome assuming you fly out of FCO

Have fun planning and traveling

In October Venice will be chilly, but if you go in May Amalfi area and also cinque terre will be hot and busy

... its a personal preference question... what weather are you more comfortable with while exploring and do you like more people around or do you want it quiet.

It would be May for me. You will have just about perfect weather everywhere. Summer crowds won't be there yet, but everything will be open and boats will be running on the AC. I would start in Venice and fly out of either Naples or Rome.

Thanks for all of the advice everyone. We will begin our planning in depth this summer once we return from a trip to Costa Rica. I look forward to bouncing my questions off of you guys!