17 days in Europe, 6 cities - too much?

I think you answered your own question. You haven't allowed for potential jet lag and the time it takes to travel between cities will eat up much of the time on your travel days. Even Vienna is off your path. Would you consider Salzburg? It's a beautiful small city with interesting day trip opportunities from there.

Agree with Andrea about it being a bit too much travel between destination. Since there is a big interest in the Czech Republic and Budapest, have you considered spending a day or two in Milan to get acclimated, and then flying there? Just a thought to consider.

Quick flying from Milan to Prague and Budapest -- that would take the sting out of train rides, and the flight fees with Ryan air come to $50-70 for advance purchase. There's an idea, I could do what Andrea suggests -- focus on a tighter Milan-Venice-Munich-Salzburg-Venice-Milan cycle , and if I do have the time, fly out to Milan-Prague and/or Budapest and back. Or does that put me back to squeezing in too much?

I guess a Eurail pass wouldn't be cost effective here, and a bunch of point-to-point tickets would serve us better?

If you consider flying between destinations, don't forget to factor in the time it takes to get to the airport, arriving 2 hours in advance, the flight time, then at your destination getting from the airport to the city center. My personal choice is to take the train if it's not more than a 6 hour ride. In 7 trips to Europe in the last 10 years, I flew within Europe for the first time this May. I flew Milan to Prague. There was a driver waiting for me in Prague, so I didn't have to deal with public transportation. It was very economical to do this.

How long will you be visiting relatives in Germany, and do they live in Munich?

Why backtrack to Milan to fly home? Choose a final city and with an open-jaw ticket you fly easily home from there. Vienna and Budapest are both wonderful cities with lots to do but not nearly as hectic as Prague can be, though I've not been there in November. From Munich you could go to Salzburg as another poster suggested, and I second it because it's a gorgeous city worth at least a couple of days, then to Vienna.

It sounds as if you're considering making a rather last-minute decision to fly to Prague or Budapest. If so, I think you won't find non-stop fares anywhere near the range you cited. Those great deals are usually snapped up way ahead of time. For example, looking at a Munich-Prague round-trip, I found a fare of $109 for mid-December but $275 for next week. Anything other than a non-stop would be slower than the train.

I agree that it's a shame to waste time returning to Munich to fly home, but I assume you've already bought your trans-Atlantic flights.

Venice to Budapest is $52 non stop on EasyJet. 1.5 hours.

Budapest to Milan is $94 non stop on Wizzair. 1.5 hours.

November 7 depart US
8. Arrive Milan
9. Milan
10. Milan
11. Train Milan to Venice (about 3 hours and about 10 euro)
12. Venice
13. Venice
14. Flight to Budapest (easyjet seats currently available for $52) 1:20
15. Budapest
16. Budapest
17. Budapest
18. Train to Munich (about 7 hours and about 30 euro)
OR, Lufthansa flies direct in 1:15 hours for $238 one way or $138 Round Trip. Yes, that’s right the round trip is cheaper. Often that way with large carriers. You could “miss” the return leg if its legal. 7 hours on a train is about 3 hours more than I can stand.
19. Munich
20. Munich
21. Flight to Milan (easyjet seats currently available for $52) 1:05
22. Milan
23. Fly Home

Actually, that's a trip I would enjoy....

The EasyJet flights? by the time you pay for all the add on's they will cost every bit of $100; more if you don't pack light.

I'm planning to be in Munich for 3 days to spend with cousins who live there, and I agree -- it is a shame I have to return to Milan to head back to NYC, but it's a return flight. I got a cheap NYC-Milan return flight for mom and me -- $450 each on delta. Arriving Nov 7th in Milan, returning JFK Nov 23rd. Thanks all, for helping me with sorting this one out! I still have a few hours to cancel my expedia NYC- Milan round trip flight to come up with something more efficient, but fares for open jaw are prohibitively costly....

Well, I agree that it would be hard to turn down $450!

I think James E has pretty much nailed it. I'd enjoy that trip too. The only thing I may change is to make Milan an overnight stop on the front end instead of the back end.

As far as using one leg of a round trip flight, be very careful. As I understand it, only do this if you are using the first part of the trip. If you miss the first leg the airlines often cancel the second half. Also consider that this may violate the terms of your membership in the airline's FF club with penalties that may include cancellation of your account. I doubt they would but you never know.

Nice looking schedule there, James. Looks like I can add Budapest, and it would be preferable to Prague given that Prague is quite a bit up north. It keeps me within that upper Munich-Salzburg-Vienna-Budapest line. Flights Budapest->Munich and Munich->Milan are a nice touch for the long legs of the trip. It follows Andrea's idea of flying if the train ride exceeds 6 hrs. Rocket's got a good point, though -- I need to look into what are the repercussions for taking only the first leg of a return flight. If the price is so cheap, I'm not concerned about the points, but if there are legal issues involved, this merits looking into... :)

I'm no attorney and I am hopelessly honest so I have never done it (I would buy the RT or ride the train), but these are all individual legs so what ever happens on that RT leg wont affect anything else. Since its the return you would not be showing up for I cant see how they could hold you liable or punish you for missing a flight.

As for the days, if you make any changes you have to do more research because discount carriers don't always fly the same route at the same price every day.

With just a little research you could come up with other combinations including Prague or Vienna or ....... I'm just a big fan of Budapest I knew about some of the flights so I could find them fast. I use Google Flights to do the searching.

Your Milan return trip I don't think is bad. Its movement in the correct direction. Just split your time coming and going to see Milan so that way the trip home is a little easier.

As for plane vs train I don't have absolutes, but everything else being the same I figure:

Plane:
Getting to airport 45 min
Arrival at airport 2 hours early
Flight time
1 hour late and getting bags
45 minutes to town
So that's 4.5 hours plus flight time (if it were Budapest I would say 4 hours and if it were Heathrow I would say 6 hours)

Train
1 hour to get to the station plus a little time to find the right track, etc.
30 minutes at the back end to get to the hotel
So that's 1.5 hours

The difference is 3 hours longer by plane, so I will take a 1.5 hour flight (total 6 hours) over a 6 hour train ride (total 7.5 hours). If its a train station I am familiar with I can shave 30 minutes off the train time. But I prefer sitting at a restaurant or a bar in an airport to sitting on a train.

So appreciative of the advice from everyone here! Thanks all for the comments on taking flights vs trains; I'll keep the short legs for trains and long legs for flights. Oh, and some new developments...

My elderly mom suddenly has a big interest in exploring more of Italy and going to ... LONDON. This came out of nowhere but since that I'm setting up this trip really for her, I'm trying to see how I can squeeze THIS one in! Sigh. So maybe I'll need to postpone Budapest for early next year...

Nov 7: Milan early morning arrival from JFK, one night in Milan
Nov 8: Milan to Florence train, 1 night in Florence
Nov 9-10: 2 nights in Florence
Nov 11: Florence to Venice train, 1 night in Venice
Nov 12-13: 2 nights in Venice
Nov 14: Venice flight to Munich, 1 night in Munich with German cousins
Nov 15-16: 2 nights in Munich with German cousins
Nov 17: Munich train to Salzburg, 1 night in Salzburg
Nov 18: 1 night in Salzburg
Nov 19: Salzburg flight to London, 1 night in London
Nov 20-21: 2 nights in London
Nov 22: London flight to Milan, 1 night in Milan
Nov 23: Milan to JFK

Net net, this whole trip comes out to:
2 nights in Milan
3 nights in Florence
3 nights in Venice
3 nights in Munich
2 nights in Salzburg
3 nights in London

I hope that sounds reasonable, and it's still early enough to make adjustments. Will need to buy plane tickets soon before they spike up. Any suggested alterations? Thanks!