We usually plan pretty far out, but for the first time in years, we haven't even planned a year out! We'll have had a really crazy year - Alaska cruise August 2015,
DCL Holiday Bahamas cruise end of 2015,
ABD Costa Rica spring break 2016, we just got back from WDW and Universal, and we're heading to Galapagos with Celebrity in August- but then we don't have anything actually booked except WDW for next spring break. (We have DVC, so at least we always have a WDW trip planned.) We've talked about several possibilities for this year's holiday season or next summer - South Africa ABD, Australia (probably not ABD, considering the new itinerary), Danube River Cruise ABD (waiting to hear back from the first trip reports!), or even a great American West type trip with friends. We travel with fairly young kids; our daughter is 5 and our son is 11. We've just about ruled South Africa out for the near future because I honestly don't think our daughter is capable of being silent and motionless for long periods of time on game drives yet. We've just had such a crazy, vacation intensive year that having very little booked after August feels really strange. (Yes, we may have gone a little overboard this year.) We feel like we're in a sweet spot where my mother and step father are still healthy enough to travel with us, and the kids are more or less old enough for serious travel.
We are still struggling some with when to do ABD and when to do the trips on our own. Between us, we speak passable English (obviously), Spanish, French, Italian, and German, and can make ourselves understood in Portuguese when we have to. We are comfortable hiring private guides and trying out local restaurants. That said, we did try ABD in Costa Rica, a place I'd previously traveled on my own, and we loved it. It was particularly good for our very, very extroverted daughter, who is happiest with other children. I also would feel safer going into some parts of the world with Disney, or another group like Tauck Bridges or Abercrombie and Kent Family, both of which we've seriously researched. It's because clear to me that my kids would prefer we do group travel for a while. There were so many really wonderful people on the ABD we tried, and it really was one of the best vacations we've shared as a family.