PLEASE help :-( I'm stuck! And pulling my hair out haha

HI guys,

My boyfriend and i are currently wrapping up our working holiday in London with a bit of travel. The itinerary is as stands:

Fly from London to Madrid, Wednesday 17th of March.
Stay in Madrid 3 nights, 17th, 18th, 19th.

Fly/Train from Madrid to Barcelona, Friday the 20th of March.
Stay in Barcelona 4 nights, 20th, 21st, 22nd, 23rd.

Fly from Barcelona to Venice, Tuesday the 24th of March.
Stay in Venice 2 nights, 24th, 25th.

Train from Venice to Florence, Thursday 26th of March.
Stay in Florence 2 nights, 26th, 27th.

Train from Florence to Rome, Saturday the 28th of March.
Stay in Rome with a friend for 5 (maybe 6) nights if ok, 28th, 29th, 30th, 31st, 1st.

Somehow get from Rome to Athens, Thursday the 2nd of April.
Stay in Athens for 4 nights, 2nd, 3rd, 4th, 5th.

Then, if able to afford it, ferry from Athens to Santorini for 2 nights and then back to Athens.

Now here are the few little problems i'm having:

I wanted to travel from Madrid to Barcelona by train but the train was sooooo much more expensive than flying. A flight was about £35 whereas the train was about £98! I was SO sure that this couldn't be right. I've also heard that the Madrid airport is really out of the way and that perhaps getting an overnight train from Paris would be a better option?

I'm also stuck on how to get from Italy to Athens. I wanted to fly but it seems rather pricey and everyone has been telling me that it's easy enough for us to just get a ferry from either Venice, Ancona or Pescara to Athens. So i started thinking that perhaps flying to Rome from Barcelona (which would again save money as it's only like 15euros on Ryan Air) and then travelling backwards through Italy would be a better option and leaving for Greece from Venice. But when i go and look on ferry websites i can't see any ferries from either of those ports direct to Athens.

I dunno...does anyone have any advice for me?!?!?!? =S I really want to book soon

There should be a bus that goes from Madrid to Barcelona, check this option out. Otherwise, assuming its Madrid Barajas airport (I think this is the main one), it is actually quite close, and is a part of the metro system so it really isn't that hard to get to the center of Madrid from here.
I'd doubt it would be very cheap going from Paris, and I notice that Paris is not on your itinerary? That being said, you could just swap Madrid for Paris on your itinerary - if you haven't been to Paris I'd recommend it. Madrid is pretty cool, nice night life, and a bit more of a Spanish feel, but I think both Barcelona and Paris are better

As for your 2nd point...I think getting multiple busses/trains and a ferry would take a long time (no idea really, but I'd say you'd probably be in transit for at least 24 hours!). Your holiday isn't very long so I wouldn't suggest this! I don't think you should bother with this option. Your 2nd option could be considered - but Venice is further away from Athens and there wouldn't be much volume of people compared to Rome so I don't know how cheap or convenient this would be.
I'd say dig a bit deeper and get a flight as it would save you a lot of hassle. Remember otherwise you'll have to get multiple tickets, and also spend money on 1-2 days on food anyway, and also have 1-2 less days enjoying the places you wanted to see.

[ Edit: Edited on 18-Feb-2009, at 15:40 by Erik85 ]