My idea of a vacation is traveling to a body of water, preferably the Caribbean but most beaches or lakes will do, setting down my beach chair, then picking up my beach chair seven days later and going home. Inertia and familiarity are key; I have been to Aruba seven times (all at the same resort) and the Mexican Caribbean four times.
I have travelled for active vacations (Walt Disney World for my kids, Ireland, Northern Ireland and Iceland for my second honeymoon, Paris for a three day weekend, a real jet setter thing to do), but my wives have planned those trips. I do, however, bring organized file folders regarding when, where and how we get to all the spots we are visiting. My second wife laughed at me when I did this for Iceland and Ireland, but it sure helped that I could pull out a pass, directions, addresses and timetables at a moment's notice. I can't be spontaneous. As I tell younger lawyers: you have plenty of things to stress and get anxious about that you can't control. Don't let the things you can control cause you stress and anxienty.