A very good point - while 'statement' smokes are cool and fun to smoke, there's not always a couple free hours on a vacation to enjoy a large smoke. I'd be temped to pack some robustos, some PC's, even some smaller smokes.
That's a good point, too.Man, I don't know. Fancy vacation cigars..............are honestly over rated. You'll worry too much about selecting the "perfect" ones, then when on vacation, they'll either let you down or you won't have enough time to truly enjoy them. Pick things you know work and that you enjoy. If I were you, I'd grab some Anniversary Padrons, whether 1964/1926 or the 40th/45th/etc. If you can find Opus/Anejos, grab those. Hell, even the Chateau Fuente SGs are great, so are their sungrown 858's.
It really comes down to what Tim stated. I tend to gravitate towards something I know works and that I enjoy, when I really want to wind down/slow down and enjoy things.