Flights from Venice to Naples are 1 hr 10 minutes and running $169 ow right now. The train is almost 7 hours so I don't think I would want to spend that long on the train.

I would head south that time of year for better (warmer) weather, but I don't like cold.

You could catch a 7 am flight from Venice and have lunch on Capri.

I will also be in Italy during that time - so BellaStar and Starrs wave hi to the frazzled Mom and daughter you see ;-)

I would add one of the extra nights to Venice and the other two to Rome or all three to Rome. Both cities are well worth the extra time and both have easy day trips you could take (Padua or Vicenza from Venice/ Orvieto from Rome)
Where in Tuscany is your rental?

Bella here again.
MomDD-there is no place better to feel frazzled than Italy, so I'll wave if I see you!

Starrs-It doesn't look as if you'll get to the AC, but just in case..
Your birthday is quite close to my birthday, and I spent it this past year on the AC. I always plan my trips for a full moon, and this year the October Full Moon will be on the 14th- so if you get there, or Capri you'll have an unforgettable moonlit sea to gaze upon.
The best way to do that is with a cocktail firmly in hand. I recommend a special refreshing cocktail to celebrate which is popular in Positano-the Sgroppino- a concoction of Prosecco, Vodka, and lemon sorbet with some wild strawberries swimming on top served in a Martini glass-maybe a splash of limoncello might be thrown in for good measure. They make great ones at Tre Sorelle down by the beach. Just one idea among many.... :)

That make just clinch that deal, bellastar. That sounds magical. I love full moons. I love warmer weather. I love the water. I love Prosecco, Vodka,lemon sorbet and strawberries. You just painted a magical picture. :-)

FF and I talked last night about the possibilities. He perked up about the Lake Como idea. He shares a dentist with George Clooney, so I'm SURE we can network an invite to his little cottage - or maybe even a ride on his boat! LOL! But, he loved the idea of Capri and area too. So many choices - as he said, how can we go wrong?!?!

kybourbon, I shared the flight idea and FF thought it was a fabulous one! Dawn, I still hope we can find ourselves in the same general area for a mini-GTG one afternoon - and other Fodorites who happen to be there too.

I do want to see Venice and Rome as well. I wasn't sure about Rome because my sister absolutely hated it - but the board has convinced me otherwise.

Ah, what a delicious quandry! Thanks for all the suggestions!

It looks as if we will be in Italy, too, for part of that time.

Starrs, we once had a gondola ride under the full moon in Venice. Absolutely unforgettable!

Byrd

Byrd, wouldn't that be a trip! We could "talk Southern" and share travel stories! kybourbon switched her dates, darn her!

Venice at full moon sounds wonderful too!

starrs,

We're still planning, but it's likely that we'll be in the CT for a few days probably starting the 15th, so we'll miss you there.

After that our plans are still up in the air, but may include Siena as a base for festival-and-winery visiting.

John and I will be traveling with another couple, with whom we've shared trips many times!

Somehow I don't think we can miss each other in Bella Italia! I'll be wearing my Fodors pin.

Byrd

It is a busy time for Fodors in October in Italy - I will be in Florence from Oct 5 - Oct 18 :))

My dearest gf might be joining us for a few nights in Italy - she is going to be in London and Germany on business in Oct as well.

It's a nice thought-I guess we'll all be "sotto la stessa luna" (under the same moon)....