Overcoming Vacation Planning Paralysis

My family is in a travel-planning rut.  There are hundreds of places on our travel wish list.  We have enough airline miles and hotel points that we don't have the break the bank to travel to many of them.  But we are already well into December and we find ourselves without Presidents Day weekend or Spring Break plans.  Next summer?  No clue.

Why is it so hard to settle on our next few trips?

1) School schedules: School calendars are bane of every family traveler's existence.  This is the first year that my daughter is in school and we are beholden to the calendar.  School holidays are when plane flights are at their most expensive and vacation destinations are the most crowded.  This is not how I like to travel.  While I'm certainly okay with allowing my 5 year old to miss a few days of kindergarten here or there, I want to make those days really count.  The destination needs to be a good one before we pull the trigger, and we are having trouble getting to that place.

2) Toddler travel companion: Our other child, our son, is now 14 months old now and entering the toddler travel danger zone.  As I've cautioned others, 12-24 months can be a really hard age for travel.  Our son is definitely a more mellow travel companion than our daughter was at the same age so we are willing to push the limits a bit more with him.  Nevertheless, we don't want to bite off more than we can chew on our next few trips.  Now is not the time to plan that once-in-a-lifetime trip to Machu Picchu.  I'm not going to enjoy it with a toddler in tow.  We need to aim for something more middle-of-the-road.  And we've simply done a lot of those kinds of trips already.

3) Deal overload: I had the hope of scoring a good travel deal during Black Friday or Cyber Monday but frankly there were TOO many deals this year.  It was information overload.  Instead, I just avoided it altogether, telling myself that there are always lots of good January travel sales that I'd wait for.  We'll see how that pans out in a few weeks.

4) Time: Planning a vacation is a lot of work!  You need lots of time to do it.  And with a job, two kids, this blog, and holiday preparation, I don't have that much of it these days.  Since we travel so much, I'm always planning our next vacation.  And sometimes it is nice to take a break from all that planning.

I don't doubt we will get back on the vacation-planning track soon enough.  One simple thing that is already helping me is to write it all down.  I'm writing down wish-list destinations, matching them up with the appropriate seasons (for example, we want to go to Iceland, but we are NOT planning that trip for February!), and then matching them up with available school holidays.  I'll keep you, my fearless readers, updated as we start to make some decisions.

Have you ever been similarly paralyzed in making your vacation plans?  What did you do to get out of your rut?  And... any ideas on where we should go these next few months?  Share your thoughts in the comments.