So many options...what to chose?

Terri,

You are indeed very fortunate in having family in Italy. A few thoughts on your plans.....

• a day trip to Lago di Como is easily possible and I'd suggest going to Varenna and take the ferry across to Bellagio if you're so inclined.
• your two night stops are only going to allow one fully day for sightseeing - will that be adequate?
• I'd suggest adding at least one and perhaps two nights to Florence, as it's a great home base for touring that area. For example, you can easily do a day trip to Siena by bus, so you wouldn't have to waste one night there which would in reality only provide a few hours for sightseeing. You could also easily do day trips to Pisa or Lucca.
• for the days 6/10 - 6/14, you could perhaps spend two nights each in Assisi and Orvieto. I wouldn't bother "return north" as your next stop is Salerno.
• your friend might enjoy at least having a look at a few of the sights in Rome, so it would be nice to fit two nights in there if possible.
• you mention "Day 15 Milan or day trip to Lake Como" - that was covered at the beginning?
• I'm not sure I agree that the weather in the Cinque Terre can be unpredictable in June - http://www.holiday-weather.com/cinque_terre/averages/june/ . If you haven't seen that area, you'd probably enjoy a couple of nights there, but of course you'd have to adjust your other destinations accordingly. Pre-booking rooms as far in advance as possible would be highly advisable. You'll also have to decide which of the five towns you want to stay in. Each of us here have our own preferences, and I prefer Monterosso.

The RS Italy 2018 would be a good choice (IMO). Be sure to get a "tutorial" from your family on using the trains and public transit in Italy, so that you don't incur hefty fines. If you could provide an indication of your "must sees", I'm sure the group here could suggest a workable Itinerary.

Good luck with your planning!

Wonderful suggestions. Thank you!

Day 1 and Day 15 were interchangeable. If we stay in Milan the first day (jet lag and all!), we would go to Lake Como on the last day. If we go to Como, then we stay in Milan the last day.

For Venice, we would arrive early afternoon (2 pm) and stay that night and another, leaving for Florence late afternoon (arriving at 6 pm). So, with that in mind, I like the idea of extending our stay in Florence and taking a bus to other towns -- Siena, Lucca or ?? I am not crazy about Pisa. I have been to San Gimignano and feel like if we see Siena we can skip San Gimignano. Any other towns?

I have been to Cinque Terre once for two days. I thought it was very crowded and expensive. But it was lovely and the focaccia is amazing. I will check out the weather and make a decision. My kids feel Rome is better than CT, but I have been so many times! I am sure I will still enjoy it though. My girlfriend is in her late 60s so I don't want to push to hard and fast.

I really appreciate the time you took to reply. I will give it lots of thought and get the 2018 guide book to fine tune.

I'd try to get a sense of what your friend likes. Would she enjoy hiking in the Cinque Terre or around Lake Como? Does she enjoy art museums? If it were me, I'd love to spend a couple days with your daughters and their families, just hearing about their lives in Italy, maybe going to the market, cooking a real Italian meal, hearing what the kids learn in school, in other words the backdoor experience par excellence.

I'd spend more time in fewer places. 2 nights gives you only one day in a place, and a lot of moving time every other day. I'd skip the CT, not because of unpredictable weather, but because of unpredictable crowds! Weather will probably be good, crowds probably huge. If your friend is a big art fan, stay 3-4N in Florence and day trip to Siena. Otherwise spend 3-4N in Siena and day trip to Florence. From my experience, Florence is always crowded and the weekends are worst. Same with Salerno - it's too far to go for just 2 nights giving you one day to visit the Amalfi Coast or Paestum - you won't have time for both. If your friend would enjoy the beach, spend an extra night in Salerno - beautiful sandy beach.

I can't imagine a 2 week trip to Italy without at least 2 days in Rome (3N) - one for ancient Rome, another for the Vatican.

We are on the SAME wave-length!

I woke up thinking that we would be away the ENTIRE time and my friend would miss out on life and culture. Sometimes, less IS more -- here more enriching. In Milan there is quite a bit to do during the day/evening (museums, shopping, Duomo, Galleria, great restaurants, cooking with my son-in-law or his mother) that we probably would not experience as tourists in other locations. I am actually thinking we should stay in Milan the first 3 days - go around the city and take a couple of day trips. I never thought of taking my friend to my granddaughter's school for an hour or so and observing the class! I am checking with my daughter about Venice for a long day or just one night (there are early morning fast trains and its about 2.5 hours). Since it is only a couple of hours, we could get to Venice by 10:30 am, spend the day and night and head to Florence late afternoon (4 pm train) the following day (in time for an aperitivo) and then plan to stay in Florence longer with day trips around Tuscany.

I want to see Umbria because I have only been to Orvieto on a day trip from Florence and I have always wanted to return and see more of Umbria.

As for the trip to Salerno, we may have to cut it in favor of Rome and just meet my daughter/son-in-law there (where he also has family).

Thanks again for the suggestions. I am feeling better about planning the trip and am going to pick up the 2018 travel guide to do some more reading.