Every year, almost like clockwork, during the holidays, we get together to visit family and friends that we haven’t seen in a while and almost inevitably, a decision is made to make plans for a “group” vacation sometime in the upcoming year. Usually the idea revolves around a cruise to the Caribbean or maybe a beach house or two in Florida but inevitably the vacation never happens.

I began to ponder why the vacation never happens and the reasons vary. Over the last decade, the reasons vary from someone losing a job and not having the funds to go on vacation to someone being ill, losing a loved one, or poor planning. On one particular year, I thought the vacation would actually happen with everyone being in full agreement that we would all go on a cruise during a particular time frame only to be thwarted by the cruise ship being fully booked for that time period!

This holiday season was no different, there is a large contingency on one side of the family that is intent on spending a family vacation on a beach house or two in Florida this year. I’m debating whether or not I should become the “project manager” for this adventure to make sure it happens but the problem resides in committing monetary funds for a group vacation from people that may pull out at the last minute thus leaving me with an oversized beach house in a location that I may not be particularly fond of for a vacation spot

I’ve never actually seen anything good come out of these group vacation though. During my youth, they did actually happen as planned but inevitably there would be branches of groups of people that wanted to do different things. One group would want to go shopping while another would want to spend the day at the beach. It begs the question, if people want to do different things, why bother with a group vacation? I think the best way to go about this is to try to plan as much of the activities and itinerary beforehand, get people’s opinions and adjust accordingly so everyone could participate at different things together.

Even doing this however would lead to a highly complex schedule and some people would still feel like they weren’t doing what they wanted to do during a vacation so is it even possible to do?