From US East Coast, to Berlin or to Munich? Which city to enter first?

You can make your decision depending on choices of flights to and from Germany.

Yeah, that’s we’ve been doing, looking at flights, and it seems like either way there’s availability and cost is very similar.

It really doesn't matter. I've flown into and out of both before and there's no real advantage to either.

That said, Berlin is a bigger and more energetic city, whereas Munich is a bit more laid back, so you might want to save Munich for the second half of your trip. It's also more quaint and scenic than Berlin, so it would probably be more fun to go from a large city to the more picturesque Bavaria. Just an opinion, but I would probably do Berlin first, then Munich.

I'm not sure what the value is of "remaining vague". Might you be abducted if you give the city name? I ask because one of the few differences between the two city choices is whether you need a two-segment flight to get to/from one of them. I have had great success with United/Lufthanasa two-segments, often paying no real extra for the second flight.

I presume you know about Oktoberfest, although I don't care much for Munich. There are an incredible number of sights between Munich and Berlin. We saw Munich from Salzburg. Are you interested in Fall wine festivals? Berlin is a very rich destination, even without the many daytrips possible. You can't spend too much time there. Are you going to the mountains from Munich, or to Dachau?

I agree with Suki; base your decision on the flights.

Where I live, a layover (or a long drive to a better airport) is a must for a flight to Europe. If this is the case for you, take a careful look at the layover airports and layover times. When flying to Europe, I like to have a couple hours of cushion at my layover airport because I don't want to miss that connecting flight. On the other hand, I don't want to be stuck waiting at the connecting airport too long because it draws out the trip too much. Also, I hate getting to the airport super early, especially at the start of a trip, so I look for flights that are at 10am or later.

Do you have a preferred airline? Do you have the opportunity to fly with a foreign carrier? When given the opportunity, my husband and I like trying out the different international carriers.

For us, the deciding factor often comes down to the actual aircraft. We are almost always in Economy. (We used to be able to find good deals on Premium Economy, but those days appear to be gone.) For long haul flights, we look for aircraft with 2 seats off to the side. Not having to sit next to a stranger on an overnight flight is a big difference maker when it comes to comfort.

Is your flight to Berlin from the east coast direct and non-stop? From SFO there is a direct flight to Munich, to Berlin, there is the lay over in Frankfurt or I can take the 5.5 hr train ride fro Frankfurt Hbf.

Can't help with the Berlin airport since I don't know it but MUC is very nice, used that once for the return to SFO.

Does your mystery location have direct flights to both cities?

If so, then its really a coin toss.
If not, then its a choice of what stopover points are involved and do you want to do it on the way there or on the return.

Have also a look at special events at both destinations (example Berlin April). In Berlin end of April anually Gallery Weekend happens.

Hint: May 1st is national holiday.

late April to early May (or if not, then October)

Like major convention cities in the US, airfare and hotel prices are subject to what will be happening in Berlin and Munich on your travel dates. Munich, for example, gets more expensive during Oktoberfest.

Go direct if you can, both ways. If not, direct to Germany and connect comming back to US.

Thanks all for these wonderful responses, giving me additional things to think about.

Our city does have direct flights to Germany, though not to either Berlin or Munich, so it’ll always be a journey with at least two legs.

I do love the suggestion that flying into Berlin will get me into a big city and then going to Munich I get to see charm and while still a big city not as big as Berlin. I think that’s a top tip for me. For now, I’m leaning towards going to Berlin first, spend about 4 or 5 full days there, then go to Munich by train and spend about 3 or so full days there.

Thanks for that website of festivals and exhibitions in Berlin organized by month! What a treasure!

While I would love to see Dachau, given our schedule I think it’s a little less realistic because we do like to spend time meandering.

If you are not flying direct to either Berlin or Munich, then you must be transferring in FRA or elsewhere. Also coming from the East coast last month, my wife and I landed in FRA and took a train to Erfurt on our way to Berlin. We spent our first two nights there. We then took the train to Berlin, stayed there about 4 days and then took the train to Munich. The train station in Frankfurt could not possibly be more convenient. On our way to Munich (Feldkirchen) We passed by Dresden, a choice. I have been there often and do not have a deep affection for it. Staying in Efurd gave me a chance to introduce my wife to a bit more "low key" Germany then immediate immersion in Berlin would have been.
To be clear, Munich is not a small town and although it is not Berlin, it is not what I would describe as "charming". It can be fun, lots of fun.

To be clear, Munich is not a small town and although it is not Berlin, it is not what I would describe as "charming".

I would. I enjoyed Munich and found it very charming especially in the evenings, and it's definitely smaller than Berlin. Don't get me wrong; I love Berlin but it is three times larger than Munich, and Munich doesn't have the high skyscrapers that Berlin does, so it seems like much more of a small city.

As @Mack said, sounds like Frankfurt. But please don't tell us as we do love to guess. So for me, it would be Munich first via train. Personally, I hate connecting to another plane after an overnight flight. I perfer to get on a train and Munich is closer to FRA then Berlin.

Flying home from Berlin to Frankfurt is OK IMO. Thought, I do like to spend the last night near the Frankfurt Airport in Gateway Gardens or at the airport Sheraton. You can fly early evening to Frankfurt, then out in the AM back to the US. You can also evaluate train vs plane from total travel time and cost perspectives.

JKH is a traveler of my own persuasion. Last month we flew to Frankfurt and immediately went to the train station and took the train to Erfurt. I am not a big fan of Frankfurt. We were planning to depart from there later in the trip (and stay at an airport hotel). Erfurt was just the right place to spend a couple nights to "adjust", enjoy a few good meals and do a bit of wandering before heading to busier Berlin. We took the train from Berlin to Munich. I like the idea of landing and getting right into the trip.