Having trouble making a decision, need your thoughts please

Have you considered Krakow?

I liked Prague for the 5 nights we were there, but I feel like that was enough. We were in Vienna for 5 nights, on the other hand, and liked it so much, we returned the next year for a week. I could easily go a 3rd time. There is just so much to do and see; art, architecture, history, music, strudel . . . Maybe that's an argument for Prague, since you have only https://www.ricksteves.com/travel-forum3 days.

"...the things I hear to be negative...." That all depends how you personally deal with it, a matter of perspective, whether that will deter you, or you ignore it, or you will go ahead regardless. Who has not heard negative "stuff" pertaining to Berlin, Vienna in particular? My take, who cares? On my first trip in Vienna in 1971, I did have a negative experience, but I figured in the whole scheme of things in Vienna, that negative experience was irrelevant, obviously, not one to deter me from a return and longer visit.

What you could encounter in Vienna in May 2018 (that's when I plan to be back again....the last week) is the heat, not yet oppressive, or rain, the crowds, always there from May to Sept. some tourist sites (Karlsplatz, am Graben, Staatsoper, Stephansdom, Cafe Sacher, Schönbrunn, etc) swamped with tour groups, no AC, (if you need that, I don't)

"...huge history buff...." I can suggest sites, memorials, monuments prior to/turn of the century in Vienna that pertain to Austrian political or military history, such as the Schwarzenbergplatz, literally a few minutes down from the big Soviet WW2 Memorial, the Deutschmeisterplatz, the Archduke Karl (Charles in anglophone historiography) statue, and of course, Prinz Eugen, to name a few , depending on your interest.

If you are there on a Sunday, there is also Deutsch Wagram, but the museum only opens once a week, Sunday. The S-Bahn from Vienna gets out there.

If you do want to spend a few days in either Dresden or Leipzig, I'd spend my overnights there, rather than trying to see either one as a series of daytrips from Berlin. So, this solves the "negative" of too many nights in Berlin.

I flew from Vienna to Berlin on Air Berlin; the flight was fine and easy. In 2004, it would have been €40 if I had booked when I first looked; by the time I actually bought the ticket a few weeks later, it was €100. So, if you do want to fly this leg, book as soon as you are sure of your plans.

I am not as fond of Vienna or Dresden as many others are, although both certainly have plenty to see that meshes with your interests. I liked Leipzig and really liked Prague. I don't think you can go wrong with any of them, so if you're really still stuck, flip a coin.

Prague!! It's so awesome there. Yes lots of tourists, but you can get away from them.

Hmmm, Stockholm would be my choice. It's a beautiful city with much to see and do in my opinion. Cheap nonstop flights to Berlin as well.

Berlin is well-situated for anything. I'm dubious about daytrips to Dresden and Leipzig - I've slept in both of those, on the same trip, for multiple days. But it depends on your travel style, and how complete you want your visit to be. Just to pick one example, anyone interested in history would want to go to the Military History (that's not the right name ... recently added to with a modern addition by architect Daniel Liebeskind ) museum in Dresden. But it is well away from the main center of attractions, and could easily occupy two or more hours, after the bus ride to get there.

I wish I had visited Prague sooner. It's just great. We did Berlin-Budapest-Prague one two-week period (5+4+4 nights), with places like Cesky Krumlov thrown in. Another trip was Insbruck-Salzburg-Munich-Vienna, very suitable for train travel.

first time I can home I brought a Sicilian who I married. next time I'm going for a German. good thing my upcoming trip is to berlin.

Berlin has two airports, both are easily accessible. Visit the wiki page for each. Toward the bottom you'll find a table with all the airlines and destinations for that airport. The world's your oyster! There's not much of anywhere that's easier to get to Berlin from by train.

If you've really narrowed it down to Vienna or Prague, I'd choose Prague with an overnight in Dresden on the way to Berlin. Dresden is a little far from Berlin for a day trip and it is beautiful after dark. Vienna, Prague and Berlin are completely different from each other.

I have not visited Prague, but of the suggestions offered, Chani's make sense.

My only other comment is that there was mention in the thread of Stockholm, and I think Stockholm is the most underrated city in Europe.

This would work better if Berlin was first stop and Como third - there's plenty in between.

What is the arrival and departure flight plan? Stockholm has been suggested for first stop (which would at least give a logical progression) but I'm thinking Helsinki. Finnair have been known to offer cheap transatlantic crossings. But that leaves the return, nearest airports for Lake Como would be Milan or even Zurich (for a PM flight).

Or possibly start in Belgium, which would from a triangular trip. Plenty of history there. Brussels has good flight options.

While "money is not really an issue" I put in a random date for a one-way flight to Stockholm (ARN airport code) and the prices were fantastic. While Helsinki is suggested as a gateway city, and having visited there and Stockholm....Stockholm is clearly the winner in my mind.

I'd suggest Vienna, as well. Between Vienna and Berlin you'll see the whole sweep of the modern era, from the antecedents of WWI up through the Cold War and Europe's recovery from it. Plus pretty art, lovely music, delicious cakes, laid-back elegance...

If those two destinations are etched in stone then you will be flying between them or spending a lot of time with ground transportation. If you are flying anyway you can throw in any other destination that has direct connections to Milan or Berlin...look at Google Flights (map) for ideas. Logistically Florence (or Italy in general) would be easy from Milan by train. You are in between seasons for Switzerland and maybe early for Lake Como but who knows with the weather anymore.

If you haven't been to Eastern Europe, you might want to consider Zagreb. It's very nice, friendly, and relatively cheap. Germanwings flies from Berlin to there.