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First time in Italy (2-week Itinerary)

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Hello! Looking for some guidance on my travel plans for Italy (for the first time ever) with my husband in May. Our plans are:

Fly into Venice. Stay 3 nights.
Take the train to Tuscany and rent a car (perhaps in Siena). We will be bypassing Florence.
Stay 4 nights in Montalcino (with day trips to San Gimignano, Siena, Pienza).
Drop off car in Orvieto, take train from Orvieto to Naples. Hire private driver from Naples to Positano. Stay 3 nights in Positano.
Use the same driver to take us to Matera. Stay 2 nights.
Back to Rome (via local train/bus to Bari, then express train to Rome). Stay for 2 nights. We will fly out of Rome.

I know we're not giving much time to Rome because I really want to see a lot of countryside. But I am debating adding an extra night at the end to Rome, if we can. We want a romantic and relaxing trip, great food, beautiful/unique scenery, and as few train changes as possible!
I was originally thinking of visiting the Dolomites for 2 nights after Venice, instead of Matera, but Matera just seems so amazing. Plus, there don't seem to be any cable cars open until very late May in the Dolomites. Also, Venice seems quite pricey to fly into, but it just seems more convenient to fly in than fly out of Venice. Any advice would be much appreciated!

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