Planning a Surprise Vacation

Posted on Posted in Planning, Surprises, Travel, Vacation

Surprise vacations, they’re the best, aren’t they? You get to surprise someone you care about with an awesome and fun vacation and you get to experience it with them– it’s a win-win for everybody!

So why would anyone plan a surprise vacation for someone else?
Next week, I am taking my best friend on a surprise vacation. The reason I planned this was because my best friend has celebrated my birthday for so many years, even going to the extent of traveling to DC, Baltimore, and Oklahoma City, to celebrate with me. And I can’t remember ever celebrating her friend! (Horrible friend, Alex!)

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I am absolutely indebted to her for so many years of great birthday celebrations and now it is her turn! I will be the designated hair holder, the bestie who finds free drinks, the one showering her with birthday surprises!

I am so excited to go and even more excited to finally tell her where we are going! I am a planner so this trip will be a blast. However, there were so many things to consider when planning and executing a surprise vacation so I would like to share some tips for those considering doing something like this in the future:

  1. Plan months in advance

Planning months in advance allows you to do a few things. It lets you to take off at the designated time of vacation, consider all aspects of the vacation, and look for great deals. The earlier you start on anything, the better.

  1. Choose the destination

It is a surprise vacation, so it’s not necessarily where you want to really, really go to. It is where the person you are surprising wants to go to (if you can afford it).

Here are some things to consider when choosing a destination for a surprise vacation:

Has the surprise (the person you are suprsing) ever been there?
Try going somewhere they’ve never been. It will be a brand new experience for them.

Have they expressed interest in going to this place?
Listen! Ask! But do so very subtly.

What does the surprisee like to do on vacation?

Are there things to do at the destination you are considering that they would want to do?

What kind of surprise vacation is this? For your significant other? Your best friend? You sibling?

For lovers, consider something romantic. For friends who love to party, a fun, lively nightlife destination! For a sister who needs a weekend break from her four kids, maybe something relaxing? Just be sure to consider them when choosing the destination.

  1. Can you afford it?

Now, you should ask yourself: can I afford this trip? Can you pay for everything you want to pay for? Is the destination feasible for your budget? If not, re-plan. Reconsider a more future date to be able to save, take on extra hours at work, do a secret Gofundme fundraiser, or choose a new destination.

Remember to work within your budget.

  1. Make sure the surprise is off or available.

Although not everyone has a 9-5 job, most do, and you have to consider the work schedule of the person you are planning to surprise.

You have two options with this:

First, you can totally surprise them by contacting their boss, explaining your plans, and seeing what the boss says. Before you do this, make sure you know what kind of boss the surprisee has. Is the boss a jerk? Will the boss be a good ally in this surprise or tell the person you are taking? Will it make your surprisee look bad if you contact the boss asking for days off on their behalf? Maybe the surprisee needs those days and wants to make them up some other way. Consider this option very carefully!

The second option is to do what I did. I just told my best friend I was taking her on a trip without telling her where we were going. She then discussed it with her fiancée and requested off at work. It is definitely not the most fun way to surprise someone but I know that my friend liked having the time to plan and get her affairs in order for the trip.

  1. Book everything early.

About four months before I booked the trip, I researched some flights and quoted myself for half of what the trip ended up costing me. I should have booked it back then rather than booking it at the end of April/beginning of May (we are leaving June 26th). Everywhere I wanted to stay had already been taken. My bad this time. Lesson learned.

For those not looking to make my mistake, check out Airfarewatchdog.com. This is the coolest flight and hotel website. It finds the best flight deals across every site; let me repeat myself, THE BEST. And it doesn’t have all those annoying pop-ups! I use it all the time. You can put in your destination from whatever airport and it will send you e-mail notifications whenever they find a cheaper flight or hotel rate.

  1. Don’t spill the beans

Make sure you are able to stay tight-lipped when it comes to the trip! No one wants their surprise ruined. I’ve almost committed this crime three times now. It gets harder the closer the date comes and the more often I talk to my friend about it. So just don’t talk about it.

  1. Plan the trip out.

This is a vacation for someone else so have a few things planned before you leave. Head on over to TripAdvisor to find out which of the local bars are the best or which tours are the most fun and worth your money.

You don’t need a daily itinerary per se, but have a few things in mind so you aren’t bumbling around

a conversation like this:
“Well, what do you want to do?”

“I don’t know, what do you want to do?”

  1. Figure out how you’re going to do the big reveal.

The big reveal, the moment the person that you care for discovers the destination location. It will be a momentous moment for both of you as long as you plan it well!

So let’s get creative! Once, we were surprised my mom with tickets to a Bob Seger concert. She thought we were going to look at Christmas lights. When we pulled up to the American Airlines Center in Dallas my dad put Bob Seger on the radio and handed her the tickets. She didn’t even look at the tickets but rather said, “Look Bob Seger is playing here. I’ve always wanted to see him in concert.” I kick myself for not recording that moment!

You might want to get more creative than that, but it’s a start. There are a million creative ways to do the big reveal! Think out of the box. Think of a destination-themed reveal. Perhaps don’t let them see the plane ticket until you arrive at your gate or blindfold them on your drive to the destination. Have fun with this! It is the best part!

  1. Reveal, then revel on your vacation!

Reveal the destination, take some pictures, post them to FB and IG, and then sit back and have a blast with the person your surprising on this surprise vacation. I know I will!

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