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Two couples, mid 50's on first trip to Italy- 2 weeks
Please give suggestions (hotels and vinyards) and what you think!
Fly to Venice, 2 nights Venice (hotel Wildner?)
train to Florence -2 nights (Hotel Torre Guelfa)
Rent car and drive to San Gimignano one overnight outside the city???
Drive to Pisa and then to 2 nights Cinque Terre (Riomaggiore (Mar Mar or any suggestions with sea views)
Do we leave the car and ferry to CinqueTerre??
to 2-3 nights Tuscany (Castello Tornano or Vill Gignamaggio??)
To Orvieto and or Civita di Bagnoregio)
2-3 nights Rome (Hotel Nazionale)
Sooo can we do it ?? How are these hotels??
thanks!!!

Go to CT after Florence by train. Pick up car after CT, visit Pisa (or perhaps train from CT to Pisa and pick up car), visit San. G and other parts of Tuscany. Drop car in Orvieto.

Sorry - IMHO you are bouncing around like a ping pong ball and don;t really heave enough time to see much anyplace. Assuming that you haven;t been to these places before - you need to allow 1/2 day at least for travel from one city to another. If I were you I would spend at least 3 nights in Venice, 4 nights between Florence and Tuscany, 2 in Cinque Terre and 5 in Rome. (I assume your 2 weeks includes 3 weekends - so you will have 16 or 17 days - if attached to a holiday.)

I agree with nytraveler. Less is more when it comes to Italy so I would pare down the number of overnight destinations to something realistic.

What time of year do you plan to travel?

In 2 weeks I would have no more than 4 hotel changes and my suggestions would be dependent on time of year and what your priorities are for the trip, neither of which you mention.

You should stay in Orvieto, not Civita. There's much more to do in Orvieto, and although I love visiting Civita, it's a day trip, perhaps combined with exploring around Lago di Bolsena.

Two week trip-max of three home bases; Rome-Venice-Florence. No car-- all train travel. Only exception if you want to drive rent for the day. Study train timetables for daytrips from these cities which are extremely well rail-connected. Slow the pace specially since this is your first time to Italy.