How Much Planning Needed for a Vacation?

While everyone is different, I feel 99.999% of us put some planning into a vacation beyond what to pack but how much planning is enough?  For my wife and I it comes down to a few factors with length and location being the most obvious.  But what about others? Time of year, group size and age, lifestyle, and budget are all big as well. 

We are planning a 2013 trip to Ireland. Having been to England and Scotland in 2011 we have a good idea of length for us.  Most guide books break it down by whats there to see and their attention span.  Compared to them I put us in the speed category of vacationers but everyone is different (the way we like to vacation is why cruising is tops on our list). 

Adding to the planning phase for this trip is the size and varied ages ( 30s to 60s) of the group.  This is where we need to give ample extra time to planning. Not everyone in our group will think less than 2 hours is enough  time for a museum for example.  So we plan out multiple options, letting everyone (hopefully) get what they want.  Sometimes it means splitting the group up for a day.  When your traveling that close together for a week or better this can be a real good thing to do.

Not everyone always has the same budget when vacationing as a group.  This can require planning as well.  Hotels are expensive in Europe but furnished flats or houses can be a steal when sharing the expense with a group. (We estimate we more than cut the cost in half last year renting a flat in London over 2 hotel rooms for a week)

Lifestyle is tricky. Not just how nice a place someone expects either. I think of dietary habits as lifestyle whether by choice or necessity. We will have 2 vegetarians with us. So in picking our location we want to make sure we have something everyone can eat. Renting a house helps with that but we dont want to eat at home for every meal so we will be checking out nearby eateries online as well.

We are looking at a 9 day vacation better from a year from now, but given the complexities we have the planning starts now and will probably add up to as much if not more time than the vacation itself. By then we will need a vacation!