First, welcome to the boards.
You can probably rely on some sun anywhere in Europe in August/September, after that it becomes more of an art. If you plan to visit anywhere in northern Europe, definitely do that when you first arrive, and then work your way south. Or, as SV suggested, you could just do a meander along the south coast - I would probably start at the Croatia/Greece end of things, working my way west. Places like Venice can get rather grey and rainy by October/November, so I'd assume Croatia would too. Malta has decent weather in October (it's taunting me now, we'd planned to go next week and can't), and then you could work your way back through southern Spain and into Portugal. Tunisia and Morocco are also good autumn destinations, if you're feeling intrepid. Hungary is probably decent in early fall - we were there in August and it was stifling. Also, Romania and Bulgaria have beach resorts on the Black Sea, but I don't know if the season extends into the fall. Check a guide book for average temps to get an idea. Also, Turkey would still be pleasant, and Cyprus.
And yes, the weather becomes increasingly unreliable as the year goes on, you'll definitely need a rain jacket and a fleece sweater or something even just for evenings.
Croatia has a fairly rocky coast, but it is popular for swimming/sunning, even so.
Are you interested in seeing cities/cultural/art/historical stuff, or more interested in relaxing on beaches and checking out the clubs scene, or ? Obviously some places have it all, but if you give us an idea of what interests you, we can probably make more useful suggestions.
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