Since this has turned into much more than koon once again punting decisions in his life to those of us on IE; some cool places that you probably have never heard of, or never considered for a vacation:
Malta: Small island in the Med., about halfway between Sicily and Lybia. Official language is Maltese, but nearly everyone speaks English. Even 90% of the signage is in English. Eclectic culture since every dynasty that has ever existed has owned Malta at one time or another)
Aqaba, Jordan: Resort area on the Red Sea(Gulf of Aqaba). Incredibly historic, yet modern Arabian city. This is the city that Lawrence of Arabia liberated, in the classic stories of his exploits. Not far from Aqaba (about a $40 cab ride(roughly 2 hrs), I think I remember) is Petra, the ancient city that is chiseled out of the cliffs that was featured in Indiana Jones and the Last Crusade. Also add a day or two to visit the Dead Sea, not far from Amman.
Varna, Bulgaria: Resort area on the Black Sea. Lots of Western hotels. Being a vacation-ey area, lots of hotel and restaurant workers speak English. Some "Old World" European charm.
Kiev, Ukraine: I would wait until the political situation settles down a bit. Once it is stable, you can't get much better in terms of Old World Charm. Fantastic city. But cold as balls in the Winter. Make it a Summer trip if possible.
Vienna, Austria: One of the exceptions to the idea that you can't get much more Old World Charm than Kiev. Fantastic city!! Tons of gothic architecture and cultural attractions.
Now that I think about it............ I think that, if you are going to go to Europe, look into the Viking River Cruises. That will let you get to many of the cultural capitals.