First, I’m a big proponent of family vacations. I’m one of the cheaper people you’re likely to meet, but I think family vacations are so important and formative and memory creative, it’s worth the money to me. So we have a “Family Vacation” envelope we deposit money from our paychecks in every month, and put a little extra in when we have the chance.
Second, I’m a pretty big proponent of cruises. They’re not cheap, but what you’re getting for your dollar can’t be beat. We just went on an 8-day cruise to Mexico – for only $400 per person. (There are all kinds of ways to get discounts on cruises, including a bunch of websites.) For that price we got … (1) a room for our whole family to stay in for 7 nights, (2) around-the-clock all-we-could-eat food – including pretty high-end dinners (I ate lobster, escargo, you name it), (3) at least one show a day – and on most days two (including improv shows by Second City, Cirque type shows, etc., etc.), and (4) transportation to Puerto Vallarta and Cabo San Lucas. I tried to estimate how much we’d pay for all that and I’m guessing around $4,000, but we got it all for $1,600.
Now there are a TON of ways the cruise will try to gouge you: Drinks, the Spa, Bingo, gifts, etc. ad nauseum. But just say no. Don’t let them take advantage of you; instead you take advantage of them.