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Italy Recommendations 9/9 thru 9/21

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Returning to Italy for my first time to hit some big cities for a 2 week vacation. It has been some time since I last visited and was just to see a friend in Paderno del Grappa and to see Venice so looking for some help. Reading up in travel books and online but would love to hear from those that have been.

There are 2 couples travelling together and we're more than happy to break off at points since our taste for what to see may differ. Open to pretty much all suggestions. The idea was to pack the beginning of the trip with the bigger tourist cities to see the history and art and then relax more on the back end.

Dates/days on trip:

Rome - arrive 9/10; depart 9/13
Florence - arrive 9/13; depart 9/16
La Spezia - arrive 9/16; depart 9/18
Lake Como specifically Varenna - arrive 9/18; depart 9/20
Milan - arrive 9/20; depart 9/21

With La Spezia, the idea is to head into Cinque Terre and walk/hike between the towns and just enjoy the scenery/food and wine. We have vacation rentals in each city with the exception of Milan where we have a hotel. We're actually headed to Munich for the last few days of the trip to enjoy Oktoberfest and see a few sites there as well. We are looking forward to eating/drinking our way through the country so if there are any great restaurants or wineries to suggest please do.

Any suggestions or tips are welcome. Thanks!

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