plan your own vacation

Why Would Anyone Want to Plan Their Own Vacation?

I’ve done some difficult things in my life. I graduated from college with two majors and a minor. I’ve battled with depression. I’ve suffered loss and grief. I’ve even made myself talk to a human at a drive-through when the Dunkin’ app sent my coffee order to the wrong store.

None of that was quite as difficult as planning my own vacation. There’s a lot that goes into planning a vacation, and if you’re like me and suffer from both FOMO and anxiety, planning a vacation can be almost impossible.

As usual, you have nothing to worry about, because I am about to give you my unofficial guide to doing something that I have no idea how to do! You are welcome. *finger guns*

How to Plan Your Vacation:

The first step is to decide on your budget, how far you want to go, and which kind of transportation you will need. Do you want to fly? Take the train? Drive so that you can stop and see the scenery along the way and have random adventures?

Everyone has a different travel style! As someone who gets motion sickness no matter what I do, I just let everyone else decide the mode of transportation, take a Dramamine, and hope for the best!

My favorite is when you take Dramamine and feel drowsy but are too anxious and uncomfortable to sleep. Be sure to add that to your travel itinerary!

Next, decide if you really want to plan it yourself. One of the best parts about living in this day and age is that we don’t only have travel agents, but we have surprise travel agents. Not only do you not have to choose flights and hotels and other crap, but you don’t even have to choose where you’re going. And isn’t that everyone’s dream? Not having to do a single thing but pay and go on vacation? I highly recommend surprise travel if your budget will allow. That way, if anything goes horribly wrong, it wasn’t your fault at all! You didn’t plan it, right?

Deciding where you’re going is probably the hardest part. If you’re indecisive like me, all of the options can lead to crippling indecision. There are so many wonderful places to explore! How am I supposed to choose which one to visit next?!

My partner Dan and I used the “Request a Recommendation” feature on Facebook to ask all of our friends and family for recommendations. This way, not only did we have several options of where to visit, but we also had people who could give us recommendations on fun things to do and delicious things to eat. Which brings me to my next point…

Figure out your priorities. What is it that you want your vacation destination to have? Tropical beaches? Lots of culture? Nature? Mimes? What, I don’t know what you like!

Pick the top three or four things that you definitely want to do while you’re on vacation and look up which places offer those things. For instance, we really wanted to go to a place with multiple cider bars. Surprisingly enough, that narrowed our list down by a lot.

At this point in your travel planning, after several fights amongst the potential travelers and multiple breakdowns, I advise that you pause here and revisit the question of whether or not you want someone else to plan the trip for you. Is this stress really worth it? Is a vacation really that much more rewarding if you plan it yourself? Will you need new friends before the trip is over after all of this fighting?

Assuming that you, for some reason, decide that planning your own trip is worth the risk, it’s time to book your tickets and lodging! Oh joy!

Here’s where the real stress sets in. Which travel dates do you pick? And what if the dates when the flights are cheapest are not the dates when the hotel is cheapest? What if you decide on a particular date, but after purchasing, you realize that flying a day later would have been cheaper? Listen to me very carefully…


Whew. Sigh. Don’t you feel better now? Since you can’t actually find any perfect combination that will cost next to nothing and give you free candy and backrubs, you now have no pressure to find those perfect bookings! Yay settling for mediocrity!

If you’re going to be like me and ignore that fact and stress out anyway, make sure to keep plenty of food and Wii remotes nearby. I always find that I can Mario Kart my stress away…or throw the remotes at the television. It helps either way.

I find the hotel to be a bit easier than the flight, because, although the prices fluctuate, you will most likely always be able to find and open room no matter where/when you go. Some people prefer to find the cheapest hotel rates, but I go a different route. I have a membership with a hotel chain where I can build up points to a free room. Sure, I may not actually earn a free room until I’m too old to travel, but hey, I can dream.

Pro tip from my bestie Stephanie: when searching for flights, be sure to use an incognito browser window so that the site doesn’t take all of your cookies and eat them and jack up the prices of your flights the next time you look (unless they’re oatmeal raisin, because then, yuck. Yep, I went there. Simply for the excuse to dis oatmeal raisin cookies).

Also, know who you’re dealing with. While there are some airlines that offer discounted rates, they are those same airlines that often have delayed flights. Surprise, surprise. Luckily, Google now has a feature that tells you if a flight is frequently delayed so that you can either avoid it or book it with dread if it’s the only one that works for your schedule/budget!

Apparently, Tuesday at midnight is the cheapest time to book flights, so use that information how you will. At midnight I am either sleeping or bribing my body to get some sleep so that I can face work with my usual sunny (read as: slightly-less-than-deadly) disposition. So either my travel buddies will be booking the flight, or we will be paying extra. I’m already going to be groggy and angry on the plane…might as well not lose more sleep over it!

On the bright side, once the hotel and flight are booked, all that’s left is to go on vacation and have fun! Besides the dreaded packing…and dreaded airport security…and the dreaded on-boarding and off-boarding process…and potentially getting lost and/or losing something once you get there. Yes, I can complain about and get anxiety over everything. It is one of my special skills. I list it between “Reciting Spongebob Seasons 1-5 Verbatim” and “Making Awful Cookie Jokes.”

Fortunately, Dan and I have survived the process of booking our vacation this year. I’m sure I’ll have plenty of travel tips for you all in the future! I just need to decide if the next one will be “Everything About Airport Security Gives Me Anxiety” or “Traveling While Short”…


Have you booked any trips recently? What was the hardest part?

9 thoughts on “Why Would Anyone Want to Plan Their Own Vacation?

  1. I can’t agree with this post! I love every aspect of planning a trip.. to the point where I plan hypothetical trips that I know I will never go on. #timewaster
    I think I missed my calling as a travel agent lol.
    I always offer to book for my family and friends too, just because I crave that rush of hitting the book button. Now they send a bit of info to me and tell me to “do my travel agent thing”

    Liked by 1 person

      1. I wouldn’t be so sure! With surprise travel agencies popping up, I’ll bet they’ll be around for a while. No one can plan their own surprise, after all!


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