What a wicked trip.
You have struck a good balance between seeing as many places as possible whilst still giving yourselves time to actually enjoy the places you visit.

I think you are going to enjoy this trip a lot.  At least I certainly hope so.

Sounds like a great trip! I think the Eastern part will certainly be worth it. If you decide to skip Zurich, you might check out the Como region of Italy, it’s great. Only other suggestion would be to visit Chefchaouen in Morocco if you can. It’s in the guidebooks, so a bit touristy, but worth it. Bus or taxi are the only ways to get there, but no worries. You’ll likely want 2 days there. Have fun!

Since I was in Bulgaria and northern Greece about the same time last year I figured I would comment on that part of the trip. I found Bulgaria somewhat interesting because it still seemed stuck to a certain extent in the Communist era. It was interesting to see the way that Bulgaria has changed since then and has learned to live with its communist past in some ways and change in others. That being said, you can probebly do Sofia in a day and maybe use another day to go to Plovdiv (which I found more interesting than Sofia if you only have one day to spare). I’ve also heard from a friend who lives in Bulgaria that the Black Sea area in the country is ridiculously inexpensive. As for Northern Greece I found Thessalonica quite boring. I was there for 1.5 days and wouldn’t recommend spending more than a day in the city. I think there are some nice day trips from there that you can take though. It is a necessary stoping point between Sofia and Athens, so it might be worth a few hours to check out and see some of Greece other than Athens and the islands. I found the most interesting part of the city was walking around and seeing the everyday life of the Greeks since I wasn’t so concerned with seeing the sites. You also might wanted to consider adding a day in Athens, I think you would be super rushed in only 2 days.

The trip looks super nice and I am quite jealous.

thanks for the comments, 
 
yabio9 did you just travel between greece and bulgaria or did you come from any other eastern courtries, romania, hungary? the travel distances are very long between these coutries to get to greece and all the way down to athens. Is it gonna be worth it for just a handfull of eastern european cities? 
 
in retrospect i wish i hadn’t purchased my eurail flexi pass, i didn’t anticipate spending this time in the eastern coutries and so little in the west.&nbspart of me thinks i should focus on the west and save the east for another trip. a trip though, that may never happen…
 
I think I will ad Interlarken or Lauterbrunnen instead of Zurich as to experience the scenic alps, but is that enough alps or should i be considering Austria too? Also i will ad a scenic route through western Germany as recomended by eurail, and ad Berlin.
 
Anyone have any opionons on skipping one of Venice Florence or Rome? and adding Cinque Terre as it does looks very nice and interesting.
 
Worst case sceneria I run out of time and have less time to spend in Spain Portugal and Morocco. Another 2 weeks would have been perfect, now i’m just getting greedy.

Romania and Bulgaria are definately worth the time, especially if you want a variety of experiences.  Its a good idea to go into the trip with a relaxed itinerary, no need to stress out and hurry through anything.  You have 3 months, just visit however many places time allows, even if that means droping a country at the end.  After a trip like this, its a good bet that there will be a next time. 
 
First off, unless you just have some diehard fascination with seeing Bran Castle (which for some odd reason a lot of people do), I would suggest substituting Sibiu for Brasov.  Its the ’07 cultural capitol of Europe and is much more friendly and charming IMHO. 
Secondly, you need to worry about getting from central Romania to Bulgaria, and about the only way to do that is through Bucharest, which is a long way from Sofia.  Why not skip Sofia, visit Veliko Turnovo for a couple days and then bus to Plovdiv and then be on your way to Greece.  If you happen to find any extra time, I’ve heard very good things about the Black Sea coast. 

I flew from Barcelona through Rome to Athens, then took a train from Athens to Thessalonica. From there it was a train to Sofia (the most interesting train ride of the trip I might add for reason I wont get into) and then I flew out of Sofia. I have a Bulgarian friend we stayed with so I’m not sure what the inter-Bulgaria travel is like as we took a car from Sofia to Plovdiv. So sorry I can’t be of help with traveling through Eastern Europe. I can say that we thought about going to up into Hungry and Romania from Sofia and it looked like it would take too much time. But you do have twice as long in Europe as we did.

thanks again for the info, i did a bit of research on Sibiu, Veliko Turnovo and Plovdiv and they definetly appeal to me more than sofia, although i’m not sure they will make the travel times shorter, i’ll probably still have to go through Sofia to get to Thessalonica.
 
Overall i’m thinking the long travel times will be worth it. Also some of the scenic routes suggested here are in my path http://www.balkanology.com/overview/article_scenicrailways.html
 
Yabio, if you have time feel fry to elaborate on: “From there it was a train to Sofia (the most interesting train ride of the trip I might add for reason I wont get into)”