During the '06 World Cup, I stayed with relatives of some local friends just outside of Cologne. It was such a beautiful City especially in the Cathedral area, with the World Cup going on it had the special vibe to go with it. Also Kolsch beer is incredible. Transportation within town and all across Germany was incredibly easy by train. Gelsenkirchen and Nuremberg were a bit disappointing to me, but had some nice qualities. Kaiserslaughtern was incredible, but mainly because the US military bases along with the USvItaly match brought out thousands of Americans and the pre-post match atmosphere was incredible.
I'm not much of a beach vacation person, but my wife is. We went to Punta Cana recently and found it to be pretty decent. Plenty of English speaking people but still a bit of local culture to be experienced. All-inclusive and an overall affordable trip. Without a doubt it's a much better value than say Miami or some other US beach locales. I've only briefly been to Hawaii during a short leave during military duty so my experience was limited, but despite being very beautiful, not so sure it's worth the cost and travel time from this region.
To put out an underdog, lesser known but relatively close town, Burlington, VT. It's such a beautiful area with plenty of things to do summer and winter. They have a very nice lakefront/downtown area right on Lake Champlaigne with great views, restaurants and pubs. There are so many very cool local craft breweries to tour within a 30 minute radius, some of them having been around before micro-brews became so hip. And of course, some of the best skiing on the east coast is available during the winter. With round trip 90 minute flights available for under $200 from NYC, It's definitely worth a trip!