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Italy Itinerary Advice Please

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We are working on finalizing our itinerary for a three week trip. We are meeting friends and visiting with Family so our locations are pretty much set, but the amount of days and order are flexible. When I showed this itinerary to a freeing who lives in Verona she said go to Lake Como first, then Venice, then fly from Venice to Lisbon. (so we don't drive across the country twice).

My girlfriend who lives in Milan says don't do that. I have no idea. Does anyone have any thoughts on this?

Also, we are debating between leaving late May or mid-June. We are concerned that towards the end of the trip (if we went mid-June) would get to hot to sightsee.

Thanks for your help!

Day
1 Departure
2 Arrive Rome - Lazy Day
3 Rome
4 Rome
5 Rome
6 Rome
7 Travel to Lucca
8 Lucca
9 Lucca
10 Lucca
11 Lucca
12 Lucca
13 Travel to Venice
14 Venice
15 Venice
16 Travel to Lake Como
17 Lake Como
18 Travel to Milan - Fly to Lisbon
19 Lisbon
20 Lisbon
21 Depart Lisbon

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