Wherever you go, you'll have a blast. October is ideal, couldn't have picked a better time. We were there last October
traveling with another couple,
first 10 days of October, and we had only 30 minutes of rain one afternoon in Rome, and otherwise 68 degrees daytime
and cool at night....just clear, pristine, sunny skies.
I'd say "under the Tuscan Sun" as it was meant to be, but that sounds too corny so I won't say it, lol.
We stayed in Rome 3 nights, Monterosso 2 nights, and Florence 4 nights.
We used our Airbnb 2BR apartment in Florence as our base for Tuscany.
https://www.airbnb.com/rooms/23580792?source_impression_id=p3_1565698391_MKDmG0iJ4LbK4/+6
I'll tell you, Florence is our favorite city without question.
The history is fascinating, and the people wonderful....not to mention the awesome restaurants.....the finer ones and
the small mom & pop ones too, which are just as amazing.
We did a guided day tour of Tuscany to Sienna, Monteriggione, & San Gimignano.....and that was extremely relaxing and enjoyable,
and having the guide certainly made it better for us.
Did a winery/farm, which was also much better having the guide.
Walking around Florence was like heaven.....we absolutely loved it, and we'll definitely go back.
Enjoyed our own private terrace in Florence at the Airbnb every afternoon.... could easily live there.
BTW, Monterosso is awesome too...by far the best of the 5 Cinque Terre towns...
lots of great restaurants even though someone said they didn't know of any.....that's silly, there are several great ones!
Love Monterosso.
Have a great time, and definitely report back to us about your trip.