So I'm trying to work through a hard time with my significant other, and I'm trying to plan a trip to Europe for the end of the summer and winter months.

First off, feel free to tell me if you think that's a bad idea because I haven't researched climates and things like that, during the winter months. We tend to like warmer weather, and were hoping to start our journey in London, because my brother lives there and it's a free place to stay for a couple of weeks, I was hoping to get some Eurail passes and go from there.

I know I'd like to see the Greek Islands, and possibly Rome...

Does anybody have any experience with a trip like this? Amazing places to go, romantic, educational... fun?

Also, a good estimation of cost for 2 people, not necessarily wanting to do the hardcore tourist style of thing, certainly looking to get off the beaten path and emerse ourselves in each culture as best we can. But at the same time not completely scrounging.

Any input would be greatly appreciated, thanks!

Your best bet is to get some good guide books that detail what you'll want to see and how to make it happen. A big bookstore will have plenty. Different publishers make books that focus on different budgets. Make sure to choose wisely by really looking through them before buying.

I have traveled all over europe with my significant other, and I have been living in italy for 6 of the last 7 years. You're in for an unbelievable experience. By the way, europe is a place with 4 seasons. Summer is warm to hot; winter is mild to very cold.