Harley and I were looking into going to Vegas for a weekend. Not because either of us like to gamble, but because we wanted to go away (and our Israel bonds matured, woot!), drink girly drinks, and wear pretty dresses. As an aside, CJ just informed me that Vermouth is not kosher, unless specifically hekshered.
We considered a number of different options for going away: Vegas, Atlantic City, Jamaica, Puerto Rico, the Bahamas, Costa Rica, and so on. In the course of this it became clear that there are a few different types of vacations that Jews like to take:
Most obviously Israel trips. Either for holidays, summers, winters, with family, friends, or birthright, Israel is the eternal Jewish destination. If you haven't gone, may I suggest Jewlicious' Birthright trip. Free, 10 days long, and it looks like lots of fun.
Other Jewish-themed trips: my friend Sarah points out "Jews seem to love Holocaust tourism masquerading as vacation." I've never been on March of the Living, a Poland-Israel pilgrimage, or really to Eastern Europe at all. One day I'll get there, but for now it seems a bit too voyeuristic.
Passover/other holiday: lots of people go away for Passover, either to Miami, to some sort of all-inclusive hotel, or another all-inclusive hotel elsewhere in the US. The final option? Israel. Israel is amazing on Passover. You can get everything catered, pre-cooked, kosher to whatever specifications you keep (gebruchts, kitniot, or sephard), and delicious. I mean, I assume. For me, Israel on Pesach is still a dream. As is Israel for Sukkot. Magical. Also, instead of two days of chag (holiday) you only have one. For those of us who are traditionally observant, that is magic. For the record, I consider Israel to be magic year-round.
Honeymoon: for the record, this is not immediately personally relevant (Aunt L, be sure to tell my father, or I will get a phone call this evening). However, I have a number of newly married/engaged friends. They will be relieved to know that there are kosher cruises, kosher all-inclusive resorts in Costa Rica, and kosher spas. And to think that I basically travel with bread, cans of tuna, peanut butter, tradition soup, and hope to be able to purchase vegetables/fruit and bottled water. Apparently, those days could be over. Granted, it probably costs an arm and a leg, but who cares? Kosher food (of dubious quality) in Costa Rica!
I don't think that I've missed any of the major ones, but Jameel points out that basically any vacation that one could want is available in Israel.