Europe - deciding where to go

Why not try to fly into Florence instead of Milan?
7 - 8 days is not a lot so stay in Florence 4 days and/or just stay in Italy the entire trip.
Otherwise you will be spending too much time trying to stay awake in transit to Amsterdam.
Or if you absolutely want to go to Amsterdam, fly there from Florence. There are direct flights

Thanks for your feedback! We did purchase Global Eurail passes on sale, so we were trying to see a few different countries (although flying from Italy up to another northern city is definitely an option). Ideally, we would choose a city or two in between Florence & one of the more northern European cities, ultimately flying out of Amsterdam (or somewhere else up north, really).

Our goal is to see a variety of countries/cities/cultures while we're there, since we've never been to Europe.

Thank you!

Have you booked your flight yet?

Limit yourself to 3 cities for 2 weeks and spend 4 days in each city so that will give you 12 days.
The other 2 days can be a travel day and the departure date.

We have not booked our flights yet. We're flying from Chicago (probably May 30 or 31) and trying to figure out which city would be best to fly into. Chicago - Milan seems to have some more affordable flights, but we're definitely open to some feedback about flights, too.

If you want to save money, then buying a Global Pass is not a terribly good start, I'm sorry to say. You should first figure out where you want to go. With your timeframe, pick 3 locations. Europe is a big place and flying might be a better and much cheaper option. Try to select cities that are closer together.

I also recommend two cities to visit in addition to Florence and Amsterdam. How about Venice and Paris?

Re: flights. I would look at multicity (aka open jaw) flights Chicago-Milan/Amsterdam-Chicago. You will save some money if you can leave on 5/30 (a Thursday) . If you fly into Milan, you will be taking a bus or train from the airport to the Milan train station, then a train from Milan to Florence. In this case, I would consider staying in Milan overnight before proceeding to Florence,

Flying into Florence would be a lot more expensive than Milan.

Our favorite airline is Aer Lingus, which offers the benefit of going through US customs and immigration in Dublin on the way home.

I'd recommend looking at travel times. We enjoyed Innsbruck, Austria a lot on our trip. You can get there by train from Florence in 5.5 or 9 hours, depending on the train. I'm not sure which trains your pass will cover, so that's a consideration. I wouldn't want to spend more than 8 hours on a train each day. Maybe 2 nights in Innsbruck, then to Frankfurt or Stuttgart, then to Amsterdam? That's potentially 3 eight hour days on a train for the 7 - 8 days you have... so break it up somehow that makes sense for your travel style.

You're trying to do too much. Sorry, but you won't see a lot of Europe from a train, and that train is going to take time away from your being in the places that you want to see. Since you already have the Global Pass, the farther the cities area from each other, the more time you will lose sitting on the train getting there. So, try to find a direct route from Florence to AMS and choose cities on that route. Either through Switzerland and Germany, or through France and Belgium. Then pick the two cities you want to see on that route (say Paris and Nice, or Paris and Brussels, or Paris and Bruges, or Bern and Munich, or Munich and a small town on the Rhine. Etc). Then calculate how long the train rides are and whether there are any sleeper trains (for example, if you were going from somewhere-in-Italy to Paris as one leg). If you spent a night on the train you wouldn't lose a day from site-seeing. You could also save Italy or AMS for a future visit (because once you go, you will figure out how to go back for less than this trip) and make a more circular route from, for example, AMS-Paris-Strasbourg-Munich-AMS. Have you looked at Seat-61 for information on the most efficient use of trains? That may help once you start figuring out a route.

Just saw this. Maybe it is useful for you too :)
https://community.ricksteves.com/travel-forum/general-europe/rome-to-munich-trip-ideas

A suggestion for your future trips: It is not a good idea to buy a rail pass (even if on sale) before you know where you plan to travel. If you pin down your itinerary early and are willing to commit to non-refundable/non-changeable tickets, buying individual train tickets well in advance can offer very good prices--far less expensive than a rail pass. Your research for this current trip may lead you to focus most of your time in Italy, in which case it might well be better to fly from somewhere in Italy to Amsterdam.

Well since you have already purchased the Rail Pass all the (good) advice to fly is useless. Since you have to travel by train, and you want a "taste" of different cities then you might as well just pick a sampling of cities in the countries between Florence and Amsterdam. If flights are substantially cheaper going into Milan then you could take the train later that same day to Florence. Four nights would then give you three full days, enough to take one day trip (Siena, bus bus). Then train to Switzerland - this will take most of the day but will have some nice scenery - though nothing like the 'best' of Switzerland. I would probably spend two nights in Interlalken which will give you one full day. If the weather is good do a day trip into the mountains, if it's not then do a day trip to Bern and another small city in that region. Then on to Luxembourg or Trier Germany. Neither of those is a 'highlight' of Europe but they are both nice enough, and more importantly they are 'on the way' and you are going to be spending a lot of time on trains as it is without detouring. Then to Belgium. Brugge is the most 'charming' town but Antwerp or Ghent are worth seeing as well. Since they are all so close you could do two nights with a day trip to one of the other towns in between. Then to Amsterdam. The whole trip will be very rushed but some people like that pace and that would give you five countries in 12 days. Almost everyone who has been to Europe a few times agrees that it is almost always more enjoyable to slow the pace and see fewer places but you have the rail passes so you are kind of locked in. I hope you got a really good deal on them. Definitely fly open jaw into Italy and home from Amsterdam.

An alternate route would be Italy - Strasbourg, France - Paris - Belgium - Amsterdam. That wouldn't be my first choice simply because you need at least 3 or 4 days to do any kind of justice to Paris and that doesn't give you enough for the rest. I think it would be frustrating.

Check flights to Bologna and Florence - we found Bologna cheaper than either Milan or Florence. And if your read enough you'll find that almost 1/2 the flights into Florence end up diverted to Bologna due to wind and the short runways in Florence.