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Help with trip planning, Rome to Milan fall 2015

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This is long, but I'm of the opinion that too much info is better than too little, so here goes. Thanks in advance for your time and help.

I’m looking for some advice on where to spend a week to 10 days between Rome and Milan this fall.

My husband & I are in our late 50’s, love ruins, history and walking, enjoy museums but prefer seeing art in place in Churches. We like good food but aren't foodies, We prefer to spend our vacation $ on espresso in a cafe in the morning, a simple lunch while we are out and cook our own dinner in an apartment before going out for an evening stroll and gelato. Or should I say passeggiata! We do not want to rent a car on this trip, but instead use trains or buses. We like to stay in one location for at least 3 nights whenever time allows. (I feel like I’m filling out an application for a online dating site.)

We were in Italy our first time in 2010; 3 nts Venice (explored using the Church pass), 4 nts Florence (gelato & Michelangelo), 4 nts in Monticiello (car trips to nearby towns, Assisi), 5 nts in Rome. Rome was the highlight of our trip, loved it all, the forums, the Churches, the piazzas, the fountains, the people. We stayed in apartments the whole trip.

Finally, we are going back. We are not rigid about exactly when, I’m thinking late September/early October. We have 2 wks or a bit more, again, not rigid about time this trip but don't want to be away from home too long.

I had planned to fly into Rome spend 7 nts, train to Naples, spend another week to 10 nts visiting Pompeii, the Amalfi Coast, staying for awhile in Sorrento or Positano then flying out of Naples or Rome dependent on cost.

While looking for flights, I’m finding airfare into Rome is considerably more than Milan:$1400. ea. prox for Rome rt or Rome/Naples opposed to $900.ea.prox for Milan rt. With a price difference like that I’m rethinking our trip.

We still want to spend 7 nts in Rome. But since we would be flying into Milan I think we should plan the rest of our trip for North of Rome instead of South.

What do you all recommend when arriving in Milan? Should we reserve train tickets for Rome that day? Or spend the night in Milan in case of problems with our flight so we don't have to worry about missing the train? We are flying out of Buffalo NY so jet lag is an issue. Maybe spend a couple nights in Milan at the beginning of the trip before heading to Rome? I’m on the fence about this.

So, we get to Rome, either first night or later. I have a list of things we didn’t have time for the first trip, including a lot more time spent just sitting in piazzas or cafes. After I get the broad plan in place I will be back for more questions on Rome.

When it’s time to leave Rome (boohoo) to ease the pain we take the train to???? Orvieto for 3 nights? Or Sienna? Both? Somewhere in the Cinque Terre area for 3 or 4 nights from where we can take some walks/hikes? I know CT gets blasted for being too touristy, but we are tourists too and can deal with that. The area sounds beautiful and would be our alternative to the Amalfi coast. If not CT, where else can we get to via train that we could spend some time walking in the countryside? I’m open to all suggestions.

At the end of the trip we are back to Milan for our return flight. We would want to be there at least a day before our flight. If we haven’t spent time there on the front end, should we plan a few nights at the end? I don’t know if we could get tickets to see the Last Supper, but from what I’ve read the Duomo is worth seeing and there is the Expo thing going on, don’t know if that would be crazy busy or not?

I can't wait to get your ideas. Thank you again.

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