vacation planner

The pros and cons of being the vacation planner

I’ve always been the de facto planner for vacations in part because I like vacation planning almost as much as I like taking vacations. But there’s a lot to be said for sitting back and letting someone else bear the brunt of the logistics. While there can be a lot of benefits to being the vacation planner in your group, there are a lot of downsides too.

The pros of being the vacation planner

Planning a trip is a lot of work, but you can reap a few rewards for your trouble. What can you get out of the effort and time it takes into planning a trip?

The process is fun

If you’re a natural planner, then looking up things to see and places to eat and the best neighborhoods to stay in feels like pregaming before you go out. Sometimes the pregame ends up being even better than the actual party. Planning gives you a sense of anticipation that makes the days and months leading up to a trip more exciting than they normally would be. The people just showing up to the vacation don’t get that. There’s nothing exciting about Venmoing someone your part of whatever great activites someone else carefully picked out for you.

You get to build exactly what you want to do into the itinerary

As trip captain, one of the main benefits is that you’re able to sell your vision for the vacation to everyone else without much pushback because your co-travelers won’t know any better. You can make time for all the sites you want to see and experiences you’re interested in, and just send it off to be approved by everyone else. When multiple people are actively planning the trip, there may be more conflicting opinions about where to stay, eat, and how to pass the time. But if you’re taking the lead and everyone else is happy to go with the flow, then you’re free to craft a trip that you’re more likely to enjoy.

You control the pace of travel

This is maybe not as much of an advantage of planning as it is a huge disadvantage of being a passive participant in your vacation. If someone else is booking activities and they’re not taking into account the time everything might take or how long it takes to get from one place to the other, you might end up on a frantic and exhausting trip with no time to rest or even eat. If you’re planning everything (and you’re good at it), you can ensure that the pace of the trip is comfortable for everyone.

The cons of being the vacation planner

Like everything, always being relegated to planning does have its downsides. Some of these make it worthwhile to let go of the reins and let someone else do all the work.

It’s time-consuming and frustrating

Sure, it might be fun, but it takes a lot of effort and time to research and plan a trip. It is exponentially more effort according to the number of people going. If you’re in charge of booking the flights and you have to get everyone’s approval before pulling the trigger, be prepared to wait one or two days for everyone to answer your email. Maybe by the time everyone agrees on something, you may no longer have the time to devote to booking everything or prices may have changed, leaving you back at square one.

You’re more likely to be disappointed

One of the biggest downsides to planning, and especially over-planning, is that you’ve already seen the idealized versions of all the things you want to do. Non-planners don’t have so many expectations, so their experience is more likely to be enjoyable one way or the other. You can’t be mad about not getting to see something you didn’t even know existed. However, if you spent weeks poring over every tourist sight and restaurant reviews and you show up to find that the fountain in the old square is under construction and the best restaurant in town is closed for holiday, you’re more likely to be bummed out about it.

vacation planner
Expectations vs. reality are only crushing when you have a lot of expectations to begin with.

It’s more stressful during the vacation

Planning a vacation is a lot like hosting a party. Sure, you’ll probably enjoy it, but never near as much as your guests. As trip planner, you have to make sure everything fits everyone’s budget, that everyone is on time for the things you planned including transportation and activities, and that the trip goes smoothly. You want everyone to enjoy their trip, which gives you added pressure. If something goes wrong, you’re the one taking the blame (“Why didn’t we book the tickets in advance if the line was going to be like this?”) When everyone else is looking around and taking pictures, you’re trying to figure out how to get from point A to point B every step of the way.

Even if you’re the kind of person who always wants to be in control, you might be surprised by how much you enjoy yourself if you pass the baton every once in a while.


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