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Eastern Europe itinerary in 20 days

My friend and I would like to begin in Talinn, after visiting Moscow and St. Petersberg, and continue on to Riga, Vilnius, Gdansk, Warsaw, Krakow, Prague and Berlin. It's ambitious and we could look at deleting but would really like to include it all. Not sure about the routing either: Vilnius to Warsaw and then Gdansk, Berlin, Prague, eliminating Krakow? Vilnius to Gdansk, then Warsaw, Krakow, Prague, Berlin? In looking at transportation (busses, trains mostly) some distances are many hours. Flying is a possibility but we'd like to see the country from the ground not the air. But, do we trade that for more time at the location? Really need some direction from those who have done it or are locals. After Berlin (or Prague) it's on to Venice and Verona before leaving from Milan. Air to and from set. Many thanks!

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I haven't been to Poland or the Baltic states, but judging by Rome2Rio.com (not always safe to do), the fastest non-flying route from Vilnius to Gdansk involves a SimpleExpress bus to Warsaw and then a train. If that's accurate, it appears that Vilnius-Warsaw-Gdansk (skipping Krakow on this trip) would be the best order.

I'll issue my usual warning here: It's a good idea to buy tickets (with seat reservations) for border-crossing buses ahead of time. I've seen such buses sell out in the Balkans. Although I'm a decide-at-the-last-minute sort of traveler, I buy cross-border bus tickets as soon as I know what day I will be moving on, and the first thing I do when I arrive in a new city is check on the bus schedule for my next planned stop. Although rail schedules are readily available online, I've found that online bus schedules can be inaccurate or incomplete, and there's no substitute for going to the bus station for on-the-spot information.

I think you should trim a few of your planned stops to allow for the time it's going to take to move from place to place and to have decent visits to the remaining cities, especially since I suspect you may not return to that part of Europe anytime soon.

Berlin, in particular, has a huge number of sights, especially if you happen to be interested in World War II or Cold War history. The art and ethnographic museums on Museuminseln are very large, and each could take the better part of a day. Furthermore, Berlin is a sprawling city. You'll spend more time moving from sight to sight in Berlin than you would expect, so the city needs more time than you'll be able to allow it if you stick to your tentative itinerary. Of course, you could do the more eastern cities and omit Berlin on this trip, since it will be easier to visit on a later trip.

One other thought: I gather that you are young and energetic, but keeping up a hectic pace through large cities with frequent long travel legs for five weeks (?) is very different from moving at that pace for just 10 or 12 days.