Too Ambitious an Itinerary?

but the cost of the two one ways right now doesn't seem worth it.

Don't look at 'one way'; look for "multi-city" ( aka open jaw) flights. Fly into Munich and home from Prague, would be one option.

Not having to back track is the only way you could execute your plan without running yourself ragged.

Have you looked at what your travel times between each of your desired locations?

Better to think of how many nights you will spend at each location to see how best to allocate your time

Happy travels

I’m still more of a day person than a night person, so I look at it that way.

1. Depart the US
2. Arrive Munich
3. Munich
4. Munich
5. Munich (it’s the main purpose of the trip)
6. Morning Train to Salzburg
7. Salzburg
8. Train, Salzburg to Hallstatt
9. Train to Vienna
10. Vienna
11. Vienna / Melk day trip
12. Vienna
13. Train to Prague
14. Prague
15. Prague
16. Depart From Prague Of course two weeks is really 16 days if you add the last weekend to it. Since you paid so much to get over there, stay till they force you to leave. Who cares if Monday at work you look like …. Well …. You know.

Yes, I took Bratislava out of it. Too many other better places to see first. But you could trade away Hallstatt and Melk for Bratislava

Your chosen cities are relatively close to one another, thinking of Europe as a whole. How are you planning to get from one city to another? Intercity travel can take longer than you may think and expect to spend close to half a day doing this for each city- packing up, driving/train travel, getting to hotel and getting settled.

1-2 days in Salzburg is reasonable - it's a small city. For the other cities, your travel group is going to have to decide on what to see of the highlights as your stays are short.

Schedule in time to do nothing, for each of you to do as you like or nothing - maybe sleeping in, doing laundry, etc.

Many/most of my European trips have involved many museums and churches, and I have learned that close to the end of the trip I tend to be "churched" out and want to do something else. I also break up church/musem wandering with something different like a tour out of the city or going to a park in the city.

Book MultiCity Tickets - NOT one way or round trip. It's always an option on all the airline sites and typically doesn't cost more at all.
Fly into one city and out of the other. It's how most of us always travel to Europe.

I'd do at least 3 nights in each town as that's only 2 full days, which is nothing. It takes LOTS of time to change locations. I think 4 days in Munich is too much. I'd do 2-3 w/a trip to Dachau Concentration Camp.

Salzburg is fabulous and I think needs 3 full days - you could also go to Eagles Nest & a Salt Mine (so fun).
Vienna def 3 days.
I'm not a fan of of Bratislava compared to your other places.

Prague 3 full days.

I realized I was using a travel portal that for some reason was way more expensive for multi-city. Looking on other sites I see the cost is pretty much the same as a round trip.

We're looking to do Bratislava because we've got Slovak roots/ancestors and want to see it. If we had more time I'd rather go to the Tatras instead of Bratislava, but I don't think that's manageable given the timeframe.

The Oktoberfest in Munich is overrated. It is nothing else than an expensive booze-up. Therefore I would go there on the late afternoon of your arrival. This will give you a deep sleep in the night, combining jet lag and alcohol. :-)

Regarding your schedule I would stay 3 days in Munich, 3 in Salzburg (day trip to Hallstatt), 5 in Vienna, skip Bratislava, 3 in Prague.

I realized I was using a travel portal that for some reason was way more expensive for multi-city. Looking on other sites I see the cost is pretty much the same as a round trip

Hope you are using 'travel portal(s)' just for research, but will buy the ticket from the airline.

This forum is littered with tales of woe of those dealing with a flight problem when having bought the ticket from other than the airline directly.

IMHO, the best search engine for flights is this: https://www.kayak.com/

As said before, always book your ticket directly, not via a third-party reseller.

If by portals you mean third party ticket sellers, probably not a good idea. But using something like Google Flights (there are others that people like) will show you exactly what is available from the airlines themselves (safer) and will show the lowest class price. Then you must visit the airline website and pick through the various class options to find one that suits you and see the price. But everything reasonably available will show up, with fairly accurate pricing on Google. But do book with the airlines.

We're looking to do Bratislava because we've got Slovak
roots/ancestors and want to see it. If we had more time I'd rather go
to the Tatras instead of Bratislava, but I don't think that's
manageable given the timeframe.

Then you have the one great exception to my comments about Bratislava. But do know that if your ancestors were from anyplace beyond Bratislava they probably had very little to do with the people or culture of Bratislava. Slovakia is a stunning country and worth the time. You dont even have to go as far as the Tatras to find some of the best of it. I would do Slovakia before Munich or Salzburg ..... but you already have your tickets. I did do Slovakia before Salzburg or Munich (never done Munich), three trips with the fourth in the planning for early this summer. But I live close by so its easier for me to do little parts at a time.

For Bratislava, the old town was "interesting" but very tourist structured. Very much like main street at Disney. So after you have done a half day or a day in old town, get out into the city and find something a little more culturally active. For that a guide would probably help.

Also watch the news before you go so you dont walk into a protest. Slovakia is a bit volitile right now, not sure how that will play out before you travel.

Oh, for Bratislava, if you stay the night, I stayed here last year. Nice hotel, good location for old town but still where you can escape easily to other parts of the town. Not cheap, but nothing in Bratislava is (still more wallet friendly than Austria): https://www.arcadia-hotel.sk/

We're somewhat tied to going to all of the cities

No, this isn't too much for two weeks. You have enough time to get a taste of each city. I wouild avoid the time it will take to travel back to Munich for a round trip flight. As has been suggested, look at multi-city flights for Munich and Prague. Also, if you have the flexibility, look at reversing your trip (Prague first) as an option as this my lower your cost of flights.

but if it doesn't make sense then I'll try to think of alternatives.

Your long haul is Prague. If you wanted to cut travel time and have a more compact trip, replace Prague with Budapest.

Long haul, or shorter, not nearly as important as seeing what interests you, but worrh pointing out.

Favorite Tourism Video of Budapest
https://youtu.be/1nd5AtZIrTk?feature=shared
Anthony Bourdain describing how visually pleasurable Budapest is https://youtu.be/0nd9DuDGCz0?si=aa0c19KaJHEtabkX