I have never signed up for a travel forum before, so thank you for your patience--and please let me know if I have broken any forum etiquette with this litany of questions embedded in one post.
My family and I (two teens, two adults) are hoping to get our plane tickets this week for a trip primarily to Italy but also Vienna. We plan to go after the first week in June for 2 weeks--so maybe leave June 12, come back June 26th, but have flexibility in arrival and departure date as long as it is 2 weeks and is an affordable option. We are seeing that it is much less expensive to fly into Munich and leave out of Milan--than it would be to fly into and out of Rome or Vienna, for example). In terms of itinerary, we were thinking
Munich to Vienna (daughter loves classical music and plays piano and cello so to her this is a must), Vienna to Venice, Venice to Rome, Rome to Tuscany, Tuscany to Milan. The first few days would be in Munich and Vienna and the rest would be in Italy. I wasn't thinking more than a full day in Venice, either, so we could spend more time in Rome.
My husband wanted to do southern Switzerland, too (originally we were going to fly in and out of Zurich because it is cheap), but he has since realized that this is likely not possible due to time constraints. Flying out of Munich instead of Zurich seems to be about the same price and also puts us a little closer to Vienna--so saves precious time--and it's way cheaper than flying in and out of Rome or Vienna.)
My questions--in no particular order except for #1, and no need to answer all if multiple queries are just plain obnoxious:
(1) Does it make sense to fly into Munich and out of Milan? This is my #1 priority question because we want to get the plane tickets asap. They seem to be getting more expensive by the minute!
(2) Is this itinerary (including my time allotments) completely nuts? I am betting a lot of you will say cut out a couple destinations, but given that we have four different brains weighing in with their preferences, my aim is just to try to please everyone! (I guess it's three brains weighing in on preferences, because I have already been to most of these destinations. :) ) I feel a little bad that my husband is giving up the desire to see Switzerland, but I am not sure there is much we can do.
(3) Eurail pass: Worth it for all countries? Or should I just by a pass for Italy? If no Eurail, do you have recommendations for alternate ways to secure train tickets?
(4) Is there still a direct overnight train from Vienna to Venice? I am seeing mixed information on that. We want to do an overnight train (OBB Nightjet) but I am seeing there are 2 changes in between, which I would like to avoid because we will probably be sleeping.
(5) We would like to go to a beach while we are in Italy. (This was a request of my teenagers because they have heard about the beautiful beaches in Italy and also would like a day to "chill.") I have researched beaches but don't know which ones are the best for a family with teens.
(6) Any favorite to-dos in Tuscany--within the context of our time constraints?
(7) Car or no car in Tuscany? Again, we are hearing it's great to rent a car there, but to me that could be a logistical nightmare. And I am reading that there are no cars allowed in some areas (e.g., beach areas).
(8) Any other gold nuggets of wisdom to offer?
Thank you so much for reading this long post--and for any and all recommendations/advice!