How to Plan a Surprise Trip

How to Plan a Surprise Trip

Picture yourself at the airport. As people rush to security screenings and their gates, you stand still with your suitcase at your side and your carry-on bag draped over your shoulder. The contents of the suitcase are unknown to you; you’re hoping no one asks you if you packed your bag yourself, because you didn’t. And more than not knowing what is in your suitcase, you don’t know where it’s going. You haven’t seen your boarding pass. Your destination is a complete mystery. Would you be up for the adventure?

Fortunately for me, Adam loves adventure.

After a few years where travel was impossible, then discouraged, then finally available to us again, Adam wanted to take a trip for his most recent birthday. We batted around a few ideas, considering domestic and international destinations, eventually leading Adam to share he just wasn’t sure what he wanted to do to celebrate another trip around the sun. His indecision switched on a light bulb for me; if he didn’t want to choose where we would go, was it possible to surprise him? What would it take to throw his version of the ultimate surprise party: a long weekend to a mystery destination?

Operation Surprise Adam was an unparalleled success when we spent a long weekend in Bulgaria for the Surva Kukeri festival, and it was worth the challenges that came with it—and there were certainly challenges.

If surprising a partner, friend, or family member sounds like a challenge you want to accept, this guide will help you plan, prepare, and deliver on an experience all but guaranteed to be among the most memorable you’ll have.

Decide the Level of Surprise

When it comes to planning a surprise trip, the big question to ask yourself is how much you want the beneficiary to know in advance. There’s a pretty big range when it comes to letting someone in on their own surprise; you might let them know the location but not the itinerary, the dates but not the destination, or you might not let them know anything at all: after breakfast, you could grab your keys and tell them to get in the car because it’s time to go. Everyone has their own tolerance for surprises, so consider the level of surprise you can feasibly incorporate into your planning.

Surva Kukeri Festival in Pernik, Bulgaria
Surva Kukeri Festival in Pernik, Bulgaria
Because Adam and I both work fulltime, telling him we had a flight to catch without warning wasn’t a possibility. He needed to request time off work, so at a minimum he needed to know the date range for our trip. I decided that would be the only element of the experience that he should know and opted to keep all other details a secret from him. If you decide to create the ultimate surprise trip, it’s helpful to think ahead about any details that could cause your loved one anxiety if they are suddenly going to be out of town. That could involve asking a supervisor if they can take time off (and ensuring the supervisor can keep a secret!), planning around busy or stressful times at work, and handling other details that your loved one usually handles on their own. Since Adam knew he would be out of town, I left those details to him—which worked well since I had plenty of my own to worry about!

Selecting the Surprise Trip Destination

The focus of any great surprise trip is the destination, and it goes without saying that picking the right destination is a big decision to make. Adam had a list of places he wanted to go that ranged from domestic spots to far-off lands, and because he knew we were going somewhere, asking for his list didn’t throw up any red flags. I took some time to research each destination based on flights, activities, and cost to understand what was possible for us.

The greatest challenge I encountered when selecting the destination was a surprise to me: I realized how much I rely on Adam to bounce ideas around when planning trips. It was tough to know I couldn’t ask him for his preference on details like which flight would be most convenient and which activity sounded like it would be the most fun. Having all of the pressure on me to make the right choices was a big change from the partnership we usually enjoy when vacation planning. Although I enjoyed it, I missed having the flexibility to be as open as usual.

Making Arrangements

The most important consideration when making arrangements was keeping Adam’s needs and preferences in mind. Once I knew we were flying to Bulgaria for a long weekend, I knew Adam would strongly prefer an evening flight to avoid requesting an extra half day off for a daytime flight. I also knew he would want a comfortable hotel with free WiFi close to Sofia’s Vitosha Boulevard, where many great restaurants are located. Keeping his preferences top of mind made a lot of my decisions easier.

Take time to organize the arrangements you’ll need to make to ensure you don’t forget any of the most important details. Although I am usually the one who handles reservations, I rely on Adam’s questions to remind me about any details I forget, like airport parking. Without his input, I relied more on lists and double and triple checking my work to be sure nothing important was forgotten.

Safeguarding Your Confirmations

Image Source: Pexels
With all the work that goes into planning a surprise trip, you won’t want anything to ruin it. I was far more aware of what browser tabs on my laptop and phone were visible when Adam was around since I didn’t want to give him any unintended clues! For the few months I spent planning the surprise trip, I was extra careful about how I handled reservations, making sure all emails came to me and ensuring no charges accidentally went to our joint credit card. I didn’t add Adam’s frequent flier number to his flight reservation until the last minute to be sure the airline didn’t send him a trip reminder. I tried to stay a step ahead of any communication that might spoil the surprise.

It’s worthwhile to think about as many trip planning aspects as possible to find ways to block details from filtering to your loved one. It’s also a good idea to think about how curious your loved one might be and how hard they might try to spoil the surprise. I knew Adam was excited to be surprised and wasn’t actively looking for clues, but if you have an amateur detective in your travel party you may need to take some extra steps to safeguard your confirmations.

Watching Your Language

While it’s important to watch your browser windows and text messages, it’s also important to watch your word choices. I realized quickly that it could be far too easy to inadvertently use words aligned to what we were doing. Adam didn’t know if we were flying or driving, and several times I caught myself as I talked about leaving for the airport or charging my wireless headphones for the flight. Take care to think about how you will talk about the trip; when someone knows they are getting a surprise, they become trained to listen for anything and everything that could be a clue.


Packing is tough no matter what kind of trip you are taking, but it’s twice as hard when you’re planning a surprise trip. Because I decided to only let Adam know when we would be out of town, he couldn’t pack his own suitcase. If he did, I would have needed to tell him about the weather in our destination, which would have given away a few too many secrets.

A week before we left, I provided Adam with four different weather scenarios, only one of which matched the weather at our destination. I asked Adam to tell me what clothing and accessories he would pack for himself if he had that option; for example, if the weather were cold, which coat and hat would he want? Would he prefer sweaters or sweatshirts? If we were traveling to someplace warm and sunny, would he want a baseball hat—and if so, which one? Adam had a lot of fun putting together his packing lists, and the scenarios were diverse enough that he had no idea which list would really serve as the inspiration for what I would put in his suitcase. Despite the fact I planned a cold weather surprise trip, I hid a few t-shirts just to keep him guessing.

Navigating the Airport

Source: Wikipedia Commons
If your experience includes flights, the hardest part of a surprise trip is handling the airport. This is where the big challenge comes into view: should you let your travel companion know where they are heading, or should you prolong the surprise for as long as possible?

My dream was to let Adam know where we were going when the aircraft started boarding, which meant I wanted to get him all the way through security before letting him find out. To accomplish that, I made sure we each had carryon suitcases so we could bypass the check-in counter. I had our boarding passes on my phone, so I could plausibly scan his ticket for him at security, and with TSA PreCheck he wouldn’t be asked to remove any of his belongings from his luggage. From there, we could proceed to the terminal, wander around for a bit, and then magically arrive at our gate just as it was scheduled to board.

If only that worked.

One detail that I forgot is that for many international flights, you need to check in at the counter before proceeding through security for a passport check. Because I skipped that step, our boarding passes wouldn’t scan, which sent us back to the beginning. As soon as we approached the ticketing counter, Adam had an idea about where we were going; our flights were on Turkish Airlines. He instantly knew we were flying to Europe and potentially staying in Istanbul, a city he hasn’t visited yet. Fortunately, he only saw the Istanbul boarding pass—not the boarding pass that would take us on our connecting flight to Sofia—so some surprises were still intact by the time we passed through security.

If you want to press your luck and see how long you can drag out the surprise at the airport, be prepared to drop the veil abruptly if you encounter challenges like we did. It’s also important to remember that, while the surprise is fun, you may need to ruin it if a security officer or other person asks questions. We knew there was a risk that someone might ask Adam about his final destination, and I knew I would need to quickly jump in to confirm it to avoid Adam looking unnecessarily suspicious. That scenario never played out for us, but having a backup plan was important.

Adding Surprises to the Itinerary

Roman theatre of Philippopolis in Plovdiv, Bulgaria
Roman theatre of Philippopolis in Plovdiv, Bulgaria
Once we arrived in Sofia, Adam knew exactly why we were there. The Surva festival only happens once a year, and it’s typically the last weekend in January. Although we prioritized our time at Surva, I also planned a surprise day in Plovdiv for a walking tour and a winery visit. Adam didn’t find out about that until just before our guide picked us up, which felt like a bonus surprise in a weekend of exciting unknowns.

When crafting a surprise trip itinerary, take a few moments to look for spaces to plug in an additional special moment or two. Great restaurants, fun tours, or stops at a specific museum can add even more to the trip as it creates a layered experience with multiple high points.

Don’t Prioritize Yourself

It may go without saying, but when planning a surprise trip for someone else, approach your efforts through their eyes, not your own. When planning a couples trip or a group trip, there is often great conversation and even debate over how to spend time by selecting activities everyone will enjoy or compromising to make sure people get to experience what is most important to them. When planning a trip designed for someone else, think about what will make them happiest. While there may be plenty of options to do things on your wish list as well, think about and incorporate items that you know would make your travel companion happy. It’s easy to plan a trip you would love—it’s harder to plan one someone else will love!

Go with the Flow and Have Fun

Our trip to Bulgaria for the Kukeri Festival was one of our favorite trips to date, and for me the best part was experiencing Adam’s reactions. I’ll never forget the smile he had when he realized he was going to Surva or his joy in revisiting a favorite restaurant in Sofia for rakia and kebapche. I was glad we left a few blank spots in the itinerary as well; we got to visit a Bulgarian music store so Adam could purchase a guitar pedal to add to our souvenirs from the trip, and we had time to explore a few new parts of the city. No trip—even a surprise trip—will be perfect, but the best memories are often made in unplanned moments.

If you have a loved one willing to take the risk that Adam did, a surprise trip is an incredible gift for them and a wonderful experience for the person planning it. I loved putting together our trip to Sofia—and I can’t wait for the next time I have the chance to plan something similar. Hopefully next time we can make it all the way to the boarding gate before the surprise is unveiled!

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