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Italy Itinerary Help!

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This is the itinerary that my husband and I planned for our trip to Italy at the end of May. It's his first time to Italy and I studied abroad in Rome 9 years ago and got to travel around quite a bit and am in love with Italia:

- land in Rome in the evening, hopefully sleep off the jet lag

- 4 nights in Rome

- day in Pompei

- 3 nights in Arienzo (right outside of Positano)

- 3 nights in Florence with daytrips to Val D'Orcia and Chianti

- 1 night in Venice (just to show it to him, but I don't particularly love it and think 1 night suffices)

- 2 nights in Lake Como

- 1 night in Milan

- Fly out of Milan

It is of course very difficult to cut anything out of the itinerary, but I also don't want us to be so rushed or to spend so much time on trains/buses that we miss the biggest joy of Italy (which is the beautiful lifestyle of relaxation).

Some specific questions:
- Would it be better to spend the last 3 nights in Milan with a day trip to Lake Como and then 1 day wondering around Milan before we fly out the next day or does Lake Como really deserve an overnight stay? Neither of us has been to Lake Como, so not sure what to expect (other than beauty).
- Since we are only staying in Venice for 1 night (IF we don't cut Venice out of the itinerary altogether), would it be a bit help to stay close to the train station? We found a hotel very close to the station, but it got mediocre reviews. We found a better option that's right by the San Salvatore water bus stop.

The biggest travel time in this itinerary is going from Positano to Tuscany. Since we want to see the Val D'Orcia and Chianti, is there a better Tuscan base other than Florence that we should go to?

Any and all suggestions are greatly welcomed!

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