How is this beginner Itinerary
 

Just trying to start sketching out something for 14 days (including travel) for trip to Italy in September :

Day 1 Fly to Rome
Day 2-5 - Rome
Train to Naples/Pompeii area
Day 6-7 Amalfi Coast
Rent Car and drive through Tuscany up to Siena (as base)
Day 8-11 Siena w/ Day trips to Florence/Pisa and Tuscany
Drop off car and take train to Venice
Day 12-13 Venice
Day 14 Fly Home from Venice

Like many other itineraries, I think it's a bit too agressive. For a 14 day trip I would probably limit it to maybe 4 cities or areas. Yes, it's possible to do much more but then it becomes a "drive by" tour of Italy. You won't see anything well but a lot of things poorly.
I would consider dropping the Amalfi coast for this trip and spend your time in Rome, Tuscany, and Venice.
Those 3 days you have in Tuscany with seeing Siena, Florence, Pisa, and perhaps other Tuscan towns will be a blur in each city. A day trip to Florence will leave you cheated on a great city, concentrate on Siena, Florence, and maybe a hill town or two in the Siena area. Pisa is about a 1.5-2 hour drive each way. Just my opinion.
[email protected]

Do you think if I split the 2 days allocated to Amalfi and added an extra day to Rome and an extra day to Siena/Florence that we could then do a day trip from Rome to Pompeii?

It would be way too much for me, but everyone has their own style and pace they are comfortable traveling. For a two week trip, myself I'd only go 3 places tops.

I think you're trying to do too much also. The 5 1/2 hr. drive from the Amalfi Coast to Siena will be a killer - consuming a good portion of the day.

I would skip the Amalfi coast, and then do the "classic" Italy itinerary

Rome 4 nights

Train to Orvieto, see Orvieto, pick up a car, & stay in the Tuscany countryside (near Pienza is my favorite area) for 4 nights. Visit many of the small hilltop villages (Montalcino, Montepulciano, San Quirico, Monticchiello, Montisi, etc), Sant Antimo abbey, walk/drive around in the scenic Val d'Orcia, soak up the beautiful Tuscan countryside.

Drive to Siena (1 hr from Pienza), visit, then drive to San Gimignano (get there after 4:30 to avoid the crowds) & stay 1-2 nights. Visit Volterra, San G. and perhaps Pisa (if stying 2 nights)

Drive into Florence, dump the car & stay 2-3 nights,

Take the train to Venice & stay 3 nights

Thank you everyone....StuDudley I really like the sounds of your itinerary!!