Vehement Solutions for Trivial Problems: Italy and Switzerland- Planning a Trip with a Detailed Itinerary

For our summer family vacation, we gave our son the same offer we gave his older sister- in celebration of his high school graduation, he could pick the destination. He loves mountains, and he told us whenever he saw a beautiful mountain photograph come up on his Microsoft Screen Saver, 90% of the time it was Switzerland so he wanted to go there. He had also taken Latin in high school, and frequently talked about his interest in Roman history, so we easily talked him into a combination with Italy, as well.

This year it was really hard to find two weeks in the summer when our schedules could all align, but we finally identified 2 weeks in August that would work. While this isn't an ideal time to visit Europe, as it is THE peak travel and vacation month, it was the only timing that would work for us and Andy got started planning.

The first step was finalizing the high-level route and areas we would visit. Andy and I have been to parts of Italy and Switzerland two times before, so we had an idea of things we really wanted the kids to see (or not). Venice was a must, as was Florence and Lucerne. I wanted to go to Milan, and Andy wanted to see Lake Como, so gradually a route emerged- we could fly into Rome, travel north through Florence, Venice, Milan, Como, Lucerne, and fly out of Zurich (avoiding backtracking by flying in and out of different locations).

With a route planned, and at about six months prior to the trip, Andy's next step was to figure out the number of days to allocate to each location, what to prioritize doing in those days, and finding any cool stops along the way when traveling from one place to the next. There are a ton of travel books, websites, etc., Andy always loves the Frommer's travel guides, as they have a good rating system of what to see, so I picked up copies of their Italy and Switzerland books. Rick Steves has good advice on the best things to see, as well.

Since August is such a peak travel time, we learned there are long queues to get to see many of the best sites and museums, or you might not even be able to see them at all if you don't book tickets in advance, so for this trip more than any other, we planned and pre-booked a daily itinerary with a great level of detail. This turned out to be challenging and time consuming for several main reasons:

Many of the advanced tickets were sold on basic websites that didn't have great functionality. The websites were in Italian only, and while we could use Chrome to translate the page, we learned for some sites you could only see and push the purchasing buttons in Explorer. So we had to use two laptops side by side, or try to hold our phone up to the screen with Google Translate to get the job done
For some tickets, there was no note on when tickets in our date-range would be released, and the release pattern we observed didn't fit much of a predictable pattern. For a few of the tickets, Andy had to check the sites regularly for several months before he could buy ones for our date
da Vinci's Last Supper in Milan were the toughest tickets to get. We had heard from several sources that the tickets can sell out the same day they're released, so we set our alarm for 2 AM on the date they were to be released (given the time zone difference) and had a bit of a frantic time using two computers figuring out how to get it to work under time pressure. It took about 45 minutes. But we got them!
One of the BEST pre-booked tickets turned out to be breakfast at the Vatican. We got in the door a full hour before general admission, and were able to spend about 45 minutes in an uncrowded Sistine Chapel

With the ticket-booking effort well underway, Andy started to plan how we would get from place to place. We love taking trains, but the train costs for 4 people were a lot higher than the cost of renting a car, so we went with the car, knowing it would be a pain and extra expense to park in some locations. Andy learned that the cost of taking an Italian rental car into Switzerland to leave it there was very high (about $800), so we opted to rent two different cars- one in Italy that we picked up in Rome (on our way out of Rome, not for use while we were there) and dropped off in Milan, then taking the train into Lugano Switzerland, where we picked up a different car that we dropped at the airport at Zurich. Most credit cards don't offer their usual rental car insurance in Italy (one of the few exception countries), so you'll want to look into coverage options separately.

Finally, Andy figured out the lodging. Hotels in Europe are generally sized for 2 occupants in a room, so Airbnb turned out to be not only a better deal for 4 of us in most locations, but gave us the added advantage of being able to cook our own breakfast, and in several of them, do a couple of loads of laundry. Andy found some wonderful places to stay, including an apartment in Rome overlooking the Vatican from its balcony, a charming B&B in the old pedestrian-only section of Como, and an actual farmhouse in Lucerne, with a herd of dairy cows right outside the door. I will say that Airbnb can be great, but we had a terrible episode trying to connect for two hours to do a key handoff in Milan when our phone carrier wasn't working and we couldn't find any wifi at all, so there are some downsides. This was also the place an apartment that was newly remodeled, but none of the three installed air conditioners would work, so we had some very hot nights.

For this trip, we emphasized seeing as many things as possible, and we kept a busy pace. This type of travel isn't for everyone, but we like to pack in experiences, and everyone did great- the frequent Italian espressos helped, too! As the trip was winding down, we all agreed that this was our best family vacation yet, and it was a testament to the tremendous amount of planning (probably at least 40-50 hours) that went into it. It's also likely to be one of the last vacations with the four of us, as the kids get ready to start careers of their own, etc., so it was really great to have this experience together.

Here is Andy's itinerary. (T)= ticket is already booked.