The Ultimate Guide to Planning the Perfect Secret Trip Your Family Will Never Forget

Over the years my family and I have taken a lot of vacations, but never a secret trip.  We have traveled extensively in the United States and abroad.  This is to say that when our family vacation planning began this past year we searched and searched for somewhere new that we have not been and at the same time was feasible given the current COVID restrictions that many international destinations still had.  This led us to search the internet for hours trying to find something new and exciting.

After hundreds of internet searches, we stumbled upon a number of companies that offered to plan a secret vacation for you.  These sites would basically gather your likes and dislikes, budget, as well as several other inputs, and book a secret vacation for you whereby you would find out your destination either at the airport or the day you left (in the case of local travel).  Our family is the adventurous type so it sounded like a fun way to vacation.

Looking at a number of secret trip companies we soon realized the two major things we didn’t like.  One, the places they would book perhaps did not give the granularity of what we wanted.  For example, it was unclear what type of hotels would be booked and even if we could be pretty specific, we lost out on the benefits of our status.  Two, the trip came at a premium that we were not willing to pay.  While a secret trip sounds like an exciting way to travel we were not willing to offset the extra costs that could have been used for the trip itself.

After significant discussion and debate we still wanted the best of both worlds, and this the story begins.  Rather than giving up either, we chose one person in the family to plan the trip without telling the others anything about it.  As I am the planner in the family, I offered to plan the entire trip with the remaining members of the family completely in the dark.  Then began what would be known as “THE SECRET TRIP”.

Destination Selection

First and foremost, I needed to find something that I thought would be fun for the whole family.  I started with grand ideas of international travel.  I looked at several options and initially landed on Japan.  Without getting into too much of the details, I actually planned a Japan trip initially (See the Japan section as this trip planning is still in the works for 2023), but ended up being delayed as Japan has yet to open to independent tourist travel as of August 2022. 

I then moved on to other international destinations, but again found the timing and COVID impact to be too much to pull off in what ended up being a 4-week period – again up until that point I had planned on going to Japan before it finally became clear that they were not going to open up.

After the false starts and most other locations not worthy of our first secret trip, I finally landed on Hawaii.  My wife and I had been to Hawaii before on a 15-day cruise round-trip from Los Angeles, but it had been a really long time and my kids had yet to visit the islands.  Combined with the fact I still had my Southwest Airlines companion pass and Southwest Airlines was having a pretty good deal on airfare (given it was only 4 weeks away), I settled on Hawaii.  After looking at a number of the islands I settled on visiting two of them, Kauai and Oahu. 

Trip Planning

Now that I had a destination in mind for our secret trip, I began to book the airfare, hotels, activities, and food.  Following my do’s and don’ts of vacation planning and my simple planning Excel sheet I laid out version one of the itinerary to get a sense of the things I thought people would enjoy while keeping the itinerary fairly open, as I was not sure what people might surprise me with (things they wanted to do or not).  I will leave the specifics of the trip itself in the Hawaii section if you’re interested in how our trip went.  For now, I will focus on the secret part.

Reveal Planning

As a general rule the companies that offered secret trips did the planning for you didn’t really focus on the reveal, but given this was mine to do what I wanted, I didn’t simply want to show up at the airport and say surprise you’re going to Hawaii.  So, while the trip itself was a bit of planning by itself and was stuff I have traditionally done in the past, I wanted the reveal to be as much an event as the trip itself.  It took a while to figure out what I wanted to do with a lot of lists and ideas but ultimately landed on using the backdrop of the movie, “Planes, Trains, and Automobiles”. 

Phase 0:  Pre-Clues

Leading up to phase 1 I tried to find little things that gave hints about the trip to come. For example, one night at dinner I made a volcano from my mashed potatoes. While another day I ordered a pineapple drink and pineapple chicken meal at a local restaurant we visited. These would become items I would later share with the family that at the time was largely unnoticed. Regardless, it was the start of a long journey of twists and turns that were to come.

Phase 1:  The Movie

For those that haven’t seen it, it’s a fairly “old” movie whereby a businessman is trying to get home from a business trip in time for Thanksgiving when his flight is canceled and he has to make his way home.  In doing so he pairs up with a bit of an oaf, a shower curtain ring salesman.  I won’t ruin the movie for you, but needless to say, they run into many issues along the way before they finally make it back.

As my wife and kids had not seen the movie, approximately 1 week before our flight I suggested we watch the movie.  At the beginning of the movie, they did not know it was related to the trip, but rather just some old movie I wanted to watch.  About halfway through I told them they needed to pay attention as it would become relevant to the secret trip that they then believed were about to find out what is was. 

At this point everything in the movie became significant for the secret trip, even though it wasn’t.  It was funny to watch them make guesses based on the cities that were in the movie, the different modes of transportation, and if I was going to pre-stage issues during our vacation.

Phase 2: The Care Package

At the end of the movie, I causally went to the back of my car parked in the garage to bring in some pre-staged care packages as well as a note in an envelope that provided some details.  In the packages were several items per person:

• Leather notebooks (TBD Link to Etsy) I purchased from Etsy that I added clues to of what the destination would be.  I made them fairly arbitrary as I didn’t want the family to already guess where their destination was.
  • In addition, in their personal notebooks, they were provided additional packing items that were not on the letter.  For my wife, it was snorkel gear, for my son a thermos bag, and my daughter was asked to create 10 paper flowers.
• What appeared like camping-type gear (basic cheap compass, first aid kit, power bars, etc.)  These were to represent hiking that we would eventually do around the volcanoes and forests of Kauai.
• Some old school activity books, as we were going to be doing a fair amount of flying and driving to get there, and to work our way around the big island.
• Puzzle boxes once solved contained an additional clue.  Box 1, Box 2, Box 3
• Sun blankets that we would later use during our trip.
• An additional riddle would lead them to another clue hidden in the house that I pre-staged earlier that day.

Now you might be asking yourself, how will one get to Hawaii on a train?  Well, you won’t.  I placed that in there with the correct time that we needed to be at the airport so they knew that there would be a long travel day ahead starting at that time, but also throw them off the scent of getting on a plane to Hawaii.  I know I wasn’t playing fair, but who says there were any rules to the secret trip?

The other item I threw in there was to get the kids more involved.  This would require them to take active participation in navigating airports, etc.  It also just happened to be that I had enough points on United to fly two people, and enough points on Southwest (after the Hawaii tickets) to fly two others.  In this case, I made it part of the game and in line with the movie theme for the kids to take control and see if they could lead each adult to the destination and meet up.

Now that they were armed with the letter and a general idea of what was next, let the games begin.

Phase 4:  The Games

What would come over the next several hours and days was nothing short of a barrage of questions about what to pack for the secret trip and get on a plane for LAX, thinking they were getting on a train when we arrived.  Little did they know what was coming.  As the clues provided in their notebooks were pretty vague in nature, I devised a number of games that would provide additional clues.

Care Package:

              The Puzzle Boxes – (Schrödingers Cat, Davy Jones Locker, Captain’s Nemo Nautilus) This was the first of two additional clues they received on day one.  I found these on Amazon and they were quite ingenious.  I would highly recommend them for this same purpose or even as a gift for someone that likes puzzle boxes or escape rooms. Each took them about an hour to an hour and a half.  Our kids were 15 at the time and my wife and I did have to help them a little, but generally, they were able to work their way through it.  Each box, once completed, contained a clue — a picture of the Chili’s restaurant logo.  Again, extremely vague at the time so the games could continue, but it was to signify a family favorite the Lava Cake.

              The Riddle – In addition to the letter there was a riddle inside.  This allowed one player to get one additional clue while we were home.   The riddle led them to a part of the house where a clue was hidden and contained a piece of paper that appeared to have roman numerals on it, with the #1 circled.  Picture if you will what that looks like.  It’s a capital “I”.  In this case, it was the first of two that would be provided during the rest of the game and signified the “I” in HI, otherwise known as the abbreviation for the state of Hawaii.

              The Notebooks – (Etsy Book 1, Book 2, Book 3) I placed 8 or so clues in each of the notebooks.  Some were similar, others were unique to that notebook.  Most were arbitrary in nature such as the longitude and latitude of one of the islands, our flight number and confirmation numbers, pictures that seemed random but referred to things that you might think of when someone says Hawaii, etc. 

Los Angeles Clues:

At this point, the family was armed with a general letter about the game that was to ensue. They had enough information to pack for something they didn’t know would be coming and as far as they knew were boarding a train when we got to LA, or so they thought.

We arrived in Los Angeles with little fan fair, kids having navigated as they needed to meet back up at the airport and check in to the hotel.  The next morning, they were told to get ready for Knott’s Berry Farm where we would spend the day, as the train ride was still several days away.

Theme Park Game – We started our day as one might at a theme park.  I am not a big roller coaster fan, but the family is.  But that was the perfect opportunity to stage the next game.  Prior to our leaving home I purchased a tube of pogs.  These were very portable, distinctive if found, and a bit of fun with interesting pictures.  While my family hit the first and second roller coasters, I went to each of the lands and hid one of the pogs by sticking it to something in that area.  I had to make sure it wasn’t in a place where some random person would find it, but not so hidden that it couldn’t be found. 

Returning to meet back up with my family, I arrive just in time as they were getting on the second roller coaster.  Just for grins, I also stuck one of the pogs on my hat I was wearing and waited until someone noticed.  I believe it was my daughter who first noticed it, at which point I announced that another game was beginning that would take place as we continued to enjoy our day at the park. 

In this game, they were provided the park map with each general area where a pug, like the one stuck to my hat, was hidden.  When we arrived in that area, they would be provided a riddle to its location.  The remainder of the day was riding rides, figuring out the riddles, and finding the pogs.  The person with the most at the end of the day received another clue.  I am told that was the best time the family had had at a theme park (the one we have been to MANY times) that they ever had.  Success.

Escape Room – My family and I like to do escape rooms, not the ones that are a single room in some random building but the movie-quality ones that exist out there (such as the Saw Escape Room in Las Vegas, which I can’t recommend enough).  In this case, we went to The Basement just outside of LA.  To make what was already a great escape room, I booked the Dead and Breakfast Package. 

While on the pricey side, it was one of the best escape rooms we’ve ever been to.  The package allowed you to have the entire place to yourself and play all 4 rooms, allowing you to experience the entire story.  Not only that, but you also got something like two times the amount of time in each area to actually complete it versus timing out and missing half of it.  In our case, we finished two of them in the normal time, and in the other two, they let us keep going until we finished.  Between games, you could spend all the time you wanted in the private party area where they had food, ping pong, console games, TV with movies, a skeet-shoot game, and a bunch of other stuff.  The package started well before their normal business hours (Like 10 am vs opening at 4 pm) and they catered to anything you may need. 

Again, I can’t recommend it enough.  The rooms were movie-quality sets, fantastic setups, and great games.  Just typing this out I get excited about it, as it was truly unlike any others we had been to.  I won’t say anymore, so as not to ruin it for you, but if you find yourself in LA, it’s a must-do if you’re into escape rooms at all.  Needless to say, we spent the next 5 hours overcoming all the challenges and playing in the party area.  In this case, the family was told that if they escaped, they would receive an additional clue, which they did.

We’ve been to LA many times and frankly, I’m not sure the family was that excited to go again, even though they knew we would be there for only two days, but I still hear today that it was one of the highlights of the trip.

Phase 5:  Initial Guesses

Before we went to bed the last night in LA, everyone was instructed to open their notebooks, review all the clues they were provided and won over the past week, and make their guess.  I can’t say the answers were too surprising considering everyone thought they were getting on a train the next morning.  As I recall it ranged from Portland to Texas to North California.  Of course, each was wrong and not even close.  I informed the family of the outcome and per the rules, we would open all the clues to everyone the next morning.

Phase 6:  The Diversion

After two days of twists and turns and complete surprises, we called it a night. They believed they were getting up early the next morning, providing their final guesses for the secret trip destination, and boarding a train to a location that would be revealed.  Little did they know, it wasn’t going to be that easy.

The next morning my wife woke up early to get ready while the kids were still asleep.  This was the perfect timing to spring the final twist.  Using the back side of the hotel room door, I proceeded to place the following letter on the door and then used the paper flowers that were my daughter’s special item to bring.  The result was a decorated door of colorful flowers with the following note:

You can imagine my wife’s surprise when she exited the bathroom and when my kids woke up.  Funny enough, I think her first reaction was “So we aren’t going on a train?”.  To this day I think she is a bit disappointed that we didn’t get to go on that train ride.  It may be a new vacation idea one of these days.

Phase 7:  The Reveal

It was now time for the final reveal of the secret trip.  Our plane left in 3-4 hours and the family had no clue where we were headed.  As the initial note indicated, they had time to review all clues and make a final guess.  I seem to recall blank faces and no better ideas than the initial guesses that were provided earlier.  At that point, I felt sorry for them and provided the final envelope that contained the following, revealing the true final destination. 

What took place the rest of the day was, I’m told, a dream.  Not only did they find out they were going to spend the next 10 days in Hawaii, but they were shocked that the day that would have started with a train trip turned into a plane trip, and as soon as our plane landed, I had scheduled a helicopter tour where we were introduced to the island of Kauai.

Outcome

From a secret trip vacation perspective, I think it will be one the family won’t forget, both in terms of the vacation itself and the equally fun lead-in.  I won’t say it was easy to plan the whole vacation myself plus the surrounding theme and games, but it seemed to be a hit.  Honestly, the hardest part was having the time to plan it while the family wasn’t around to see what was being done and then keeping it a secret without spilling the beans.

To learn more about Hawaii and what we did, go to the Hawaii section under travel. 

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