My wife and I got to talking about plans for the new year today, as you do, and have sketched out our plans for May. I could really use some input into routings and maybe together we can find a creative solution that minimizes expenses. Broad strokes are as follows:

• looking to leave MSP on either May 14 or May 15
• need a one-night stopover somewhere on the way to our first destination (MXP, BLQ or somewhere else nearby) - this can be either somewhere on the East Coast (not ATL) or a destination in Europe we can get to nonstop from MSP (AMS, FRA, DUB, CDG, maaaaybe LHR, probably not KEF)
• absolutely need to be in Ravenna on May 17th (the day before the F1 Grand Prix in Imola)
• planning on spending the 19th in Ravenna, then making our way to Venice for a couple of days
• we then need to make our way to Czechia for about five days, split between Prague and Brno, order doesn't matter
• on or around the 28th, need to position somewhere either, once again, in Europe or the East Coast for an overnight before flying home
• we've got about 120K Delta miles, 37K Virgin Atlantic points, 200K Amex points, 120K Chase points and 150K Alaska miles to play with

So far, the best I've come up with is something like this:

• MSP-JFK
• JFK-MXP on Emirates (30K points plus taxes per person, A380 is a big draw as I've not flown on one yet, but it's not mandatory)
• Rent a car at MXP, eventually drop it off in Venice OR just stick to trains the whole way in Italy
• One of two options here: either (1) fly Treviso-Prague, spend a couple days there, make our way to Brno and then either to Vienna or back to Prague, or (2) train via Vienna to Brno (or fly), spend a couple days there, then train/drive to Prague and fly home from there
• Depending on which choice we make above, fly home from either Prague (one direct flight to JFK, but can also position to a hub in Europe) or Vienna (likely more options)
• Fly home either back from JFK or wherever we end up picking in Europe

I'm sure there are plenty of things I'm missing here, so any help optimizing this trip would be hugely appreciated.