Having trouble deciding on destinations

I think your concern lies mostly with what other people will think of your choices. Of course you can enjoy those places in Poland as much as more "blockbuster" places if your mind is open to them - why not? They're interesting in their own right - no need to compare against Prague or Budapest. Moreover, you'll enjoy them on a much smaller budget as Poland is very inexpensive. I would add Zakopane, Zamość, Malbork Teutonic Castle, Kazimierz Dolny, and Łódź to your list. Look up any other UNESCO sites and see if they are interesting to you. You can easily have a long vacation just in Poland and you can easily get around via train or Polski Bus. May is a nice time to visit (it can get crazy hot in June).

You can take a look at this thread as well
https://community.ricksteves.com/travel-forum/trip-reports/poland-what-a-bargain

Why should people be shocked when somebody with Polish roots is visiting Poland and not neighbouring countries? It looks quite natural to me. And why would you enjoy those Polish places less than the popular destinations such as Vienna, Prague or Budapest? It's not all about major museums and magnificent churches.
The former poster has given you a good list of interesting places to visit. I can add beautifully situated Torun, and Czestochowa, famous for the pilgrimage for the Black Madonna.
Travelling is best done by train. Except for some express trains, they can be slow, but punctual and very cheap.

Mike, it is hard to suggest destinations when we don't know how many days you got. Let people be shocked that you did not see Prague, Vienna, Budapest. If you have two weeks go for Krakow (from there day trip to Auschwitz), nearby Zakopane in Tatras mountains. From Zakopane take a trip to one of the most beautiful mountain lakes anywhere - Morskie Oko (Sea Eye). It's right under the tallest mountain of Poland - Rysy. Then Warsaw. While it's not an immediate eye candy like Prague or Budapest, you will still be pleasantly surprised. It has some kind of charisma. Visit museum of Warsaw uprising, famous Stalin's skyscraper called by locals Stalin's dick, park Lazienki - huge, with a lake and chateau inside. Old Town was beautifuly rebuilt. It has authentic feeling unlike in Munich which center was also rebuilt but I cannot help myself, feeling is artificial. Then Gdansk. Very pretty, I consider it even more than Krakow. Take a boat to see Westerplatte where WWII started. Visit excellent Museum of Solidarity. That's where the beginning of the end of communism started. In the docks of Gdansk. Go and see castle Malbork, the largest gothic castle of Central Europe if not all. You can do it as a day trip from Gdansk or on your way from Warsaw to Gdansk or vice versa. Between Gdansk and Gdynia there is a spa and beach resort Sopot worth visiting. Then go farther to the end of long and narrow peninsula. At the end is a little town with an interesting name Hel (just one L but sounds the same). When we were there in last May it was cold and drizzly. We sent few postcards to our friends: Many greetings from Hel. We expected it hotter here.
With 3 weeks I would still stay in Poland and see more of it. Torun, Wroclaw, maybe Mazurskie Jezera (Lakes) in summer. With 4 weeks I would start thinking about including Prague, Vienna, Budapest. All above mentioned trips are best done by train. Exception: Krakow - Zakopane, Zakopane - Morskie Oko. Those by bus.

Mike, since you have Polish roots, why not try to find the place of your family origins? Assuming that it is within current borders.

My personal preference is to visit one country at a time and see as much of it possible. People who will say you should have gone to Prague, Budapest, and Vienna, are just repeating things they have heard or really want to talk about their trips.

Wow, the wealth of knowledge on this forum is unmatched! I really appreciate the insight. Looks like I'm going to Poland :)

One last question: Would there be a specific order of seeing these cities? Should I fly into Gdansk to begin and end in Krakow or vise versa? If it doesn't matter, no big deal but I thought I'd ask.

I'll probably give myself 2-3 weeks for this trip. Thanks again for the amazing recommendations.

-Mike

Should I fly into Gdansk to begin and end in Krakow or vise versa?

If you're flying from the US, it's likely that you'll find the cheapest fare and best connections into Warsaw (of course, you should confirm this as I may be wrong), so I would start there. Any flight to another city (Gdansk, etc) will go through Warsaw anyway so that would entail an additional stopover. From Warsaw, you can take trains in any direction.

As a first step, price the flights and see if open-jaw tickets are doable (otherwise, flying into and out of Warsaw may be best).

Let's put it this way: last May I spent 8 days in Poland and then went on to Prague; Prague is beautiful but honestly, if I had spent the rest of my trip and then some just in Poland I would have been ecstatic and completely satisfied. I chose Poland on a whim because I also love history, particularly WWII, and it far surpassed all my expectations. It stands out as a country that I will definitely be re-visiting, hopefully soon. I have also been to Vienna and Budapest and loved them, but perhaps this trip could just be all about Poland for you.

If you care to dig you'll find my trip report from June 2015, and there's recently been passionate discussion about Poland on another's trip report ("Poland--What a Bargain!"). I was there the 3rd week of May and it was not horribly crowded, just a pleasantly busy vibe that I really liked.

In short--I started in Krakow for 4 days (day trip to Auschwitz by guided tour, otherwise completely solo), took the train to Warsaw and spent 4 days, with a long day trip to Gdansk by train--don't miss seeing the Westerplatte, where WWII began in Europe. Then I flew to Prague. Poland is well-served by rail so you could easily get around to various smaller towns that way.

I faced this same dilemma last year. I decided to go for almost three weeks in Poland rather than visit some of the top cities in Central/Eastern Europe. I had a great trip. But since I haven't been to any of those other cities, I can't tell you my trip was better. I feel pretty confident that you will have a great time with either option. Since you are Polish, that sounds like a good reason to focus on Poland.

For us, it made sense to fly from the US into and out of Warsaw. We then did a circle - Warsaw, Gdansk, Torun, Poznan, Wroclaw, Krakow, Zakopane and back to Warsaw. Please be aware that the trains in Poland are quite inexpensive and super efficient. Every train we took left and arrived exactly on time. So you will find it very easy to get around.

I wrote a trip report which you can find under Trip Reports (duh); it's called Poland - What a Bargain. You might want to look at it for some ideas about the cities we visited. I have to tell you though, that I have zero interest in nightlife, so it won't help you there.

Mike, last time I looked, LOT (United partner) flies direct to Warsaw from Chicago, JFK, and Toronto. So that would be your best option, either coming or going or both.

If you have interest in nightlife, university cities with a lot of young people around (Krakow, Wroclaw, etc) will do the trick...Warsaw as well.

I also recommend spending more time in Poland. I am pretty well traveled and went to Poland for the first time in 2014 and was blown away by the beauty, the museums, historical sites, restaurants. It is so much more sophisticated than I had imagined (based on my impressions of my American-polish relatives...)

Poland is also a great bargain. We are going to return this year. I also recommend trying to find family there. I made the effort in the past year and found relatives in two families that are very excited to meet us!

Mike, I think your Poland trip will be fantastic. As others have suggested, if you are coming from the US, you will probably find flying in and out of Warsaw works well, with train travel to the other cities you mention. Be sure to visit Malbork Castle outside of Gdansk.

I realize many tour companies package together the main cities from Poland, Czech Republic, Austria, and Hungary. However, these are culturally and historically very different countries and I think it's difficult for a traveler to really appreciate any of these stops when they're cobbled together as "The Best of East Europe." Imagine if someone wanted to learn about the Americas by doing a blitz tour of Quebec City, Washington DC, Mexico City, and Cuzco? What a tiring and confusing experience that would be! I think your plan to explore one country at a time is a good one. Enjoy!

Mike, My husband and I are taking a 16 day tour of Poland in June. The tour takes a circular route beginning and ending in Warsaw.

Hi,
I am not of Polish background, no matter, went to Poland on three separate trips starting in 2001, very hospitable, lovely people, aside from being very affordable, good food, etc. You need not concern what others think by your not visiting Prague, Budapest, or Vienna. If you have the time and the desire, then add these places to the itinerary, or save them for the next trip. Of course, I started my visit to Poland by visiting Warsaw first, then Krakow. My priorities on these three trips were to focus mainly on cities...Warsaw, Krakow, Gdansk, Torun, day trips to Malbork to see the fortress and also Chelmno in the lower Vistula area. Choose and prioritize which places to see based on history, museums, night life, etc. What's your overriding interest in Poland?

Would I make another trip(s) to Poland? Absolutely, numerous places of interest to me historically, places like Poznan, Szczecin, Grudziadz, Wroclaw, the lower Vistula area with such towns Gniew (survived the war intact ie, the war passed it by), Kwidzyn, Pszczyna (southwest of Krakow, missed it after the visit in Krakow because of a tight time schedule), Katowice, Malbork (the town itself), Tczew, ( where the train to Malbork stopped), Przemysl (eastern Poland).

On your interest in WW2...include Westerplatte when you visit Gdansk. Definitely Krakow and Warsaw where I ran into in each city a big memorial to Katyn, in Warsaw the Polish Military Museum, as well as the Warsaw Uprising Museum with explanations on the front wall given in at least 5 languages.

Hi Mike,

I take it at this point you're planning to just focus solely on Poland? If so then that's an excellent choice, for in my opinion you can visit Prague, Vienna and Budapest on a future trip.

Five months ago I was in Poland for three weeks, spending time in Kraków, Warsaw, Toruń and Gdańsk. It's safe to say my time in Poland was one of the most wonderful and enjoyable trips I've ever taken, and I'd love to return to Poland at some point. :-)