I would look for a flight from Vienna to Dubrovnik. 6 to 8 hours by train from Vienna to Zagreb plus another 6 to 8 hours to Split plus 4(????) hours bus to Dubrovnik does not seem like a fun day. Try www.europebyair.com as many Air Croatia flights honor their $99 flight pass.

Ferry from Croatia to Italy will be tough in January. There are frequent ferries in summer with a greatly reduced ferry schedule in spring and fall. I don’t know if there’s any service in winter. Try
http://www.find-croa… for ferry scedules
You will find fast (roughly 4 hours on the EurostarItalia trains) and frequent train service from either Bari or Ancona to Rome.

Have you bought the rail pass? A 21 day pass would save $200 and since you wouldn’t need to validate it until you left Amsterdam and it could expire as soon as you got to Rome, it should work. A 10 day flexipass would save another $100 and probably cover your trip. A Select pass to cover France, Benelux, Switzerland, Germany and Austria and a couple of cheap
flights and point to point tickets will be cheaper still.

About your destinations. Brussels: 1/2 day see the medieval square, eat a waffle, have some chocolate, then head to Brugges for the rest of the time or take day trips to Brugges and Antwerp. Vienna 1 day playing tourist (schonburg palace and wandering around) rest if the time in Bratislava or taking day trips to Salzburg and/or Innsbruk

Thanks for the advice! As far as the pass goes, yes I already have it. I looked at what you said about the select pass and flights etc but decided to spend the extra money for the one month pass so I don’t have to worry about anything. Also, I plan on taking at least one day trip from each of the dest by train. Again, thanks for the info, and if you think of anything else please let me know!