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Italy/Portugal Planning Assistance

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Hello,

I am planning a trip for a friend and for all of my travels have received some great advice here, so I figured I'd ask for some more help.

The travelers are a VERY active, recently retired couple who love great food and shopping, being outside, the ocean, and some cultural activities, but not too much. My biggest concern about their plans so far is if they will have enough time in the Cinque Terre and in Florence.

Any feedback on their travel plans, itinerary, or suggestions for places to eat/things to do would be greatly appreciated. Thanks in advance!

Leave Tuesday, from Newark, 6:30 PM and arrive in Milan at 8:40 AM nonstop.

1 night in Milan
Train to Cinque terre, possibly Monterosso?
3 nights in Monterosso
Train to Florence
3 nights in Florence
Train to Venice
3 nights in Venice
Fly to lisbon, rent a car
6 Nights in Lisbon area (this portion of the trip isn't optional - they are receiving a free stay in a friend's vacation home as a retirement gift.
Fly home nonstop to newark

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