It started out as just a dream of a vacation. Somewhere to take our boys (currently 4 years and 17 months), where we would all have fun. Last year we took Max (our oldest) to an indoor water park resort for a couple of days and left Simon with my parents.
So we picked a time-frame for this dream vacation (Spring 2012), and started throwing out ideas. A return to the water park resort was at the top of the list, financially speaking. We could go for a long weekend for under $1000 (for the cost of the room) but we would have to go in February for the best rates. And in February, all the areas of the park wouldn't be open, or be open only on the weekend, which meant that a couple of our days would be spent just in the room.
So...we tabled that idea as a "maybe" and moved on to another idea.
Tropical family all-inclusive resort? Flying. Flying with a toddler and preschooler. That does not scream "VACATION!" to either of us, especially with security (aka TSA molestation) being what it is lately. We would fly if we had to, but neither of us wants to do that.
We live in Indiana if you didn't know. So that means that anywhere we want to go is far away.
I looked into all-inclusive resorts here in the continental US. Yeah....most are open seasonally, Memorial to Labor Day. The best one that is open year round--Club Med in Florida--is so ridiculously priced that it was never an option.
Looking at other resorts in warmer weather areas (because we were looking at early spring at this point and were thinking to maybe take a beach vacation), the price for rooms is so nuts that it wasn't cost friendly. On top of the price of rooms in most resorts, we would have to pay for food and activities. And many don't have any activities for preschoolers or toddlers.
When you have a budget, and a relatively small one at that, it's very hard to find a vacation idea that will work for both adults and small children.
Honestly, going to one of those all-inclusive resorts in the Caribbean would be the best for us--kids can play outside, nice rooms, food/drinks/childcare included. But...out of price range, plus flying...Next!