Appreciate Help for Route including Prague, Vienna, Budapest, Krakow

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I'm so happy I found this website; I'm having a very challenging time trying to determine an itinerary and would very much appreciate any assistance that can be provided.

My husband and I are travelling to Eastern Eujrope on Sunday, October 9 and hope to return Monday, October 24.  We are flying from Toronto, Canada and would like to visit Prague, Vienna, Budapest, Krakow. I'm having difficulty trying to determine the best city to fly into and out of and whether to go clockwise or counter clockwise.  We are in our mid-60's, fairly active and can travel on any mode of transportation; would of course prefer to book beforehand because we'll be challenged with the languages.  Your advice please? Thank you!!!

Taking into consideration your desire to book tickets in advance, probably the best way to travel is Prague-Budapest-Vienna-Krakow, because for all those legs you can actually purchase discounted international tickets online, so it will serve two reasons at once - having online tickets in advance and paying less because all those are sold with discounted fare.
Prague-Budapest: easy to use Czech Railways eShop - https://www.cd.cz/eshop/international/search_int.aspx?tt=4 (Prague-Budapest tickets start from 19 EUR).
Budapest-Vienna: Hungarian Railway website is a bit more complicated, because interface is only in Hungarian now, but manageable with google translate - http://www.mav-start.hu/imap.php?mid=ausztria . Discounted tickets start from 13 EUR. If you don't want to involve with their online system, then you can actually purchase same tickets at the counter in any Budapest international ticket office, purchase in advance (at least 3 days in advance required). If you aren't lucky to get discounted tickets, then regular fare is 25 EUR.
Vienna-Krakow: Austrain system is rather easy as well - https://ticket.oebb.at/bin/frame_ticket.pl?ticket=jticket.pl&LANG=EN (various time options and tickets from 39 EUR).

p.s. if you actually have really good offer for flying in/out other cities (not Prague and Krakow), then let us know, because change in itinerary isn't really crucial, so it might make sense to save on airplane tickets, but change sequence of visited cities.

Thank you for your sage advice which is valued and for the time you took to respond to my inquiry.  I have on hold, a fairly good airline ticket Toronto-Krakow - we would then like to visit Budapest-Vienna-Prague and can leave from Prague. Would the same ticket references apply?  Or, we could change our flights to arrive in and out of any city at a rate which is almost the same.  I'm more concerned about how to travel by train inbetween these cities and the most efficient city to fly into and then out of. 

Hmm... Krakow as starting point and Prague as final destination...well, it is doable as well. The only problem here is that Polish Railways doesn't sell international tickets online, so the only way to get them is already in Poland (or use an outside agency=pay comission).
Krakow-Budapest: limited amount of discounted tickets as well available, but again purchase in advance required, thus you will need to try to buy them as soon as you get there, but even then no guarantee that discounted ticket will be left for your date. Couchette from 39 EUR, sleepers from 45 EUR. Regular tariff for the route is rather high - 79 EUR + sleeper reservations. (it is possible to avoid such high fare, but then you will need certain tariff tricks, so if you are interested - we are ready to explain your moves here)
Budapest-Vienna: already discussed above
Vienna-Prague: same website as before - https://ticket.oebb.at/bin/frame_ticket.pl?ticket=jticket.pl&LANG=EN , discounted tickets start from 29 EUR.

Well this is starting to make more sense to me and thank you for taking some of the mystery out of the options.  If we wanted to keep this route would you recommend it the opposite way?  Fly into Prauge-Vienna-Budapest-and leave back to Canada from Krakow? Would that be easier to book? The challenge seems to be to and from Krakow. Would it be easier to book Budapest to Krakow than Krakow to Budapest?  I apologize in advance if I'm being obtuse; I;'m usually pretty savvy at booking independently but find the train system between the countries confusing.  Thank you again!

If we wanted to keep this route would you recommend it the opposite way?  Fly into Prauge-Vienna-Budapest-and leave back to Canada from Krakow? Would that be easier to book? The challenge seems to be to and from Krakow. Would it be easier to book Budapest to Krakow than Krakow to Budapest?

Well, Prague-Vienna in Czech railways website eShop start from same 19 EUR, but Vienna-Budapest start not from 13 EUR (on the contrary to Budapest-Vienna), but from 19 EUR, but at the same time already mentioned Austrian railways booking system is easy and in English. Budapest-Krakow can be bough from Hungarian railways website in advance (offer Sparnight, fares already mentioned in the first post), but the only inconvenience is partly Hungarian language interface (as we said, rather manageable with google translate or we always happy to clarify anything not clear).
So at the end, the actual question the your flight tickets. If offer to one of the cities is much better than to the other one - rail travel is manageable in all of the cases.

We have firmed up our plans and are flying Toronto-Vienna-Krakow and then from Krakow to Budapest by train in October.  We would like to take a one way overnight direct train Krakow-Budapest departing Krakow 21:57 arriving Budapest 8:35.  First of all, confused as to the difference between a couchette and a sleeper.  My husband and I would like a bed-type accommodation rather than sitting.  I have been unable to find a typical Sparscheine fare for this journey and have contacted an agency who are quoting 514PLN for 2 passengers + 30 PLN to pick up the ticket in Krakow.  I can't find anywhere, what the actual Sparscheine fare is to see how much I'm paying for commission.  Are these type of tickets sold out early and would we be taking a risk of having to pay full fare if we wait until Krakow?  I was hoping to be able to purchase in Krakow three days prior to our journey but I'm worried that a sleeping accommodation won't be available and of course, I would prefer the lower price. Can you please advise if you know what the sparscheine fare is this trip and if it's a good idea to wait?  Many thanks.

First of all, confused as to the difference between a couchette and a sleeper.

Couchette is either 4 berth or 6 berth compartment, looks something like this - http://upload.wikimedia.org/wikipedia/commons/c/c4/Liggvagnskupe.jpg , berths on both sides of the compartment
While sleeper it's max 3 bed compartment (which is as well sold as double or single), look something like - http://infokolej.pl/files/thumbs/t_wlabouz_monciak-krup_wki_tourist_116.jpg , beds will be only on one side of compartment.

My husband and I would like a bed-type accommodation rather than sitting.

There is no sitting carriages in this case, so it's either couchette or sleeper for direct overnight Krakow-Budapest.

I have been unable to find a typical Sparscheine fare for this journey and have contacted an agency who are quoting 514PLN for 2 passengers + 30 PLN to pick up the ticket in Krakow.

Discounted ticket (in this case specific type of Sparscheine called SparNight) cost 45 EUR for one person in 3 bed sleeper or 49 EUR for one person in double. For which type exactly they quoted you 514 PLN? If the later, then you will overpay around 30 EUR + those additional 30 PLN, if the former - around 40 EUR + 30 PLN. But make sure agency didn't quote you the couchette fare
Also be careful with agencies, sometimes they might not serve you well and you will end up with no ticket and trouble returning money.

Are these type of tickets sold out early and would we be taking a risk of having to pay full fare if we wait until Krakow?

Well, the number of discounted tickets is limited, usually only few out of whole carriage are sold under such discount, but it's difficult to guess when SparNight tickets will be sold out. Everything depends on day of the week, regular or holiday season etc., thus we can't guess definitely here. From our experience in general, 3 days in advance your chances are rather low, but still you might get lucky. Full standard fare Krakow-Budapest ticket+sleeper reservation (double) on the day of departure will cost you 100 EUR per person.

Just wanted to extend greatest appreciation for all of your ideas and for taking the time to answer my questions.  We have booked our overnight sleeper from Krakow to Budapest with an agency (Polrail);  we wanted to ensure that we have the tickets at a bit of a discounted rate and with our limited time in Krakow, we won't need to spend any extra time at the train station navigating through the language and purchasing the tickets.  You provide an excellent service to travellers.  Thanks again!  G. Clamen, Toronto, Canada

We unfortunately had to reschedule our trip to Eastern/Central Europe in October because of a death in our family and are rebooking for middle of May.  I had purchased tickets in advance through an Agency for 2 adults in a sleeper overnight Krakow to Budapest at the Sparscheine rate of 98E total for 2 and received good service and got the tickets well iin advance by mail.  Can you  please advise what the fare would be if I had purchased the tickets at the train station in Krakow?  We were not able to use the tickets because they were non-cancellable and non-refundable so lost the $$$  and are wondering whether it's worthwhile waiting until we get to Krakow this time.  Or, if there isn't much of a difference between the agency fare and buying at the station, I just might try the Agency again to avoid any possibility that the tickets won't be available.  We will have 4 days in Krakow before leaving for Budapest.  Any advice please?

Sorry to hear that you had to change plans because of such unpleasant event. Concerning your question

Can you  please advise what the fare would be if I had purchased the tickets at the train station in Krakow?

In case you purchase it in advance (>3 days) you still have a chance to get same Spar tickets for 45 € (3 bed sleeper) or 49 € (double). But during the high-season chances to catch such Spar tickets only 4 days in advance are pretty low, since there are only a few of those sold per carriage, thus you will have to settle with regular standard fare tickets instead (can be bought up to departure). In this case full fare ticket Krakow-Budapest (for the route of the overnight train, thus via Czech Republic) as of now cost 79 € + 21 € for the double sleeper per person. So in total 2 passengers pay 79*2+21*2= 200 €, which is basically twice as much as you payed for the Spar tickets.

Regarding advice, we would probably recommend not to make any moves now, since anyway tickets for May aren't on sale yet and won't be any time soon, plus there are might be some change in the Spar offer itself, timetable etc., thus it's better to come back to this issue like early spring, when all the options will be clear and definite, afterward again reconsider all pros/cons and make a choice.

That's good advice.  Thank you.  Will check back in April on this board.  Wishing you a good holiday season!

Will check back in April on this board

You can do it even in March, since ticket sale for this route should start around 60 days in advance

Wishing you a good holiday season!

As well wishing you the best and hope long waited trip to Europe will worth your while