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1st Trip to Italy: Must split up trip last minute! HELP!!

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Everyone who has helped my husband and I plan our first trip to Italy has been so helpful, and well, we could really use your help now as my husband has just thrown a little loop. He will not be able to travel for very long in September now so we will have to plan two trips. A longer one and shorter one and one trip will have to be end of june or july. (only time we can travel without messing with work and yes i know its not the most ideal time to travel there) We could really use some advice. This is what we have come up with so far:

We will be leaving NYC and flying to NICE
Day 1: arrive in Nice
Day 2: NICE
Day 3: Trips to Monaco and ??
Day 4: Train to Santa Margherita
Day 5: SM and Portofino
Day 6: SM or Portofino or Cinque Terre
Day 7: Train to Venice
Day 8: Venice
Day 9: Verona
Day 10: Venice
Day 11: Back to NYC

Should we add on 2 days to see another city or Lake Como? We obviously enjoy the sun, the sea, sightseeing, relaxing, not being stuck in museums all day, but seeing some amazing sights. Being that we have to travel now in the heat of the summer for Italy, we thought being by the coastal areas would be nice.

Our shorter trip which will take place in September is planned like this:
Day 1: arrive in Rome
Day 2: Rome
Day 3: Rome
Day 4: Rome/ Train to Florence
Day 5: Florence in the AM/ Rehearsal & Dinner for brother's wedding
Day 6: Wedding
Day 7: Florence and/or Pisa to see Tower
Day 8: Back to NYC

One question is: Will we totally be missing out on the Amalfi Coast? I have always wanted to go, but can always keep that as a separate trip to make us come back. Ive heard it can be just too crowded in the summer??

Please help with any advice or opinions. Its always greatly appreciated!!! Thanks!

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