How to Surprise Someone with a Trip (+ the 3 Bonus Gifts That Came with My Mystery Vacation)
For my birthday this year, my husband gave me what has got to be my favorite birthday present ever. He planned a surprise trip for just the two of us, and left me guessing the destination for months, right until we got to the airport! SPOILER ALERT: If you want to play along and guess my mystery trip destination, see my destination reveal post BEFORE you read this.
We learned a lot from our first surprise trip experience, and now that we’ve done it once, I’m hooked! This might have to become a birthday tradition in our family.
Read on for our advice on planning a surprise trip if you want to give the gift of travel (and, as it turns out, several other gifts, too).
“Ooooh Mystery” or “AAGHH Surprise”?
Quick note: I suppose I should call this a “Mystery Trip” instead of a “Surprise Trip” because the fact that we had travel plans was not a surprise.
You might say potato, potAHto. But I do see a difference. And having been on the receiving end, the “mystery trip” method is definitely the way I’d recommend doing it for two reasons:
One is to remove any potential and unexpected stress. (“Oh, no, if I’d known we were leaving today I wouldn’t have booked a dentist appointment tomorrow,” etc.)
Two is because if the trip is a total surprise, you’ll miss out on giving all the extra gifts below.
Why Give a Surprise Trip?
These are the bonus gifts that I didn’t expect to be rolled up in this one birthday trip, even though I knew it was coming:
BONUS GIFT #1: Not dreading another birthday
I knew when we were going, and I said yes to the idea months ahead of time – which actually made me feel excited for my birthday for the first time in years. That was Phase One of the gift.
I just didn’t know where we were going – like the travel equivalent of a trust fall.
And I definitely think that’s the best way to plan a surprise trip! You skip over any wondering whether the person actually wants to travel, or wants to travel that week.
BONUS GIFT #2: Daydreaming
After all, my favorite thing about this mystery trip wasn’t the shock of suddenly having plans for the week. It was daydreaming about going somewhere, which has been one of my life’s most consistent hobbies. Ever since I was a little kid spinning a globe and saying, “Mom, I’m going to go to Hong Kong! I’m going to go to El Salvador!” (Which I now have!)
If the gift had been “Surprise! We’re going somewhere today!” it would have taken away Phase Two of the gift: those daydreamy months of just knowing I had travel plans.
BONUS GIFT #3: Lightening the mental load
But perhaps the biggest gift of all was Phase 3: Not having to plan.
I’m not necessarily the biggest planner anyway (shocking for a travel writer, maybe?). That’s because I love the natural mystery of travel, and would rather not know exactly what to expect in a destination before I get there.
But this surprise took that to a whole new level. The things I got to skip:
- Having to research and choose a hotel (which I normally do, because I am… how can I put this… legendary at it. Not to be surpassed, my husband absolutely killed the hotel choice. 10/10. Our little bed and breakfast was cozy, waterfront bliss, with local owners, a perfectly central location, and a pool. I might even get to start delegating this task in the future.)
- Wondering whether I remembered to… look up whether I needed to pack plug adapters, for example. (For the record, Bermuda uses the same plugs as the US, so we were good there. But I didn’t have to Google it. He did.)
- And all the other minutiae we think about before traveling. They were all off my mental load, and I just got to be excited. (Like a little kid before their birthday! So of course kids love them – fun plans on the calendar, but no responsibility for them? Yes please.)
NOTE: Are you reading this and thinking “but my partner LOVES planning, if I do it for them it would take their fun away!”?
Well, respectfully, maybe you’re wrong about that. Hear me out:
Maybe your partner is really good at planning, and has always taken on that responsibility. And at the same time, maybe they would actually love an opportunity to not be in the driver’s seat.
So maybe just float the idea to them… “hey, how you feel about if I took you on a mystery trip for your birthday and I planned everything, and you could just relax and enjoy?”
They might love you just for bringing it up.
In which case, don’t back down now – and don’t screw it up. Here’s our advice to get you started:
How to Surprise Someone with a Trip
There are a couple of travel companies I’ve found that will plan every detail of a surprise trip for you. But as Emanuele proved, you can definitely do it yourself! Especially if you’re a reasonably experienced traveler, and/or you don’t require a packed scheduled when you travel. (Trust me, traveling slowly, without too much planned, never hurt anyone.)
If you go DIY, these are our tips for planning your mystery trip:
1. Choose “dull but beautiful.”
That’s how the 1999 travel guide to Bermuda, which we found among the poolside reading material at our B&B, described this little country. And no, that wouldn’t normally sell me on a destination, but it was perfect for a 4-day mystery trip!
That’s because “dull” meant safety, simplicity, no chance for overwhelm. If the trip had been to say, Iran or Lebanon (two places that have been on my travel bucket list forever), I would have felt like I needed to have done research.
But a small island less than 2 hours away that speaks English, flies the union jack, and doesn’t often make the news? It was a perfect place to relax and just enjoy the views.
2. Let the person being surprised be in on it a little bit.
If there something really important to them and their travel style, don’t ignore it.
Are they an obsessive, exacting foodie, who only travels for great meals? (Note: don’t take them to Bermuda.)
Do they really want to vacation in hot / cold weather?
Love / hate cities?
Finding out if your person wants a chance to at least put some kind of basic restriction on the destination is great advice for most people… but it’s advice we actually didn’t follow. (My only restriction was a direct flight.)
As you can see in our video of me guessing our destination at the airport, I had NO IDEA where we were going. And for me, that was perfect. I wasn’t stressed about it.
Emanuele and I have traveled to dozens of countries together, and we know each other’s travel styles and broad ranging travel interests. (Wine tasting in Napa? Absolutely. Middle of nowhere in China? Sign me up. E-biking through Italy? Heck yes.)
He knew that I would love just about any new destination, just for the newness.
3. Go low-commitment
A short trip and a fairly close destination are perfect – especially for the first time you try a surprise trip gift.
Short duration and short travel time both create a lot less anxiety than getting to the airport and suddenly finding out you’re about to be on a 16-hour flight to… Cambodia, for example.
And whether you’re a frequent traveler or not, going somewhere for 4 or 5 days feels approachable. It’s an amount of time that makes it easy to be okay with being without something you might have forgotten to pack, for example.
Speaking of packing…
4. Specific packing list, or packing for them?
Those are your two options, so choose wisely. It’s up to you, and it’s definitely personality-dependent, but don’t leave this up to chance.
We did a hybrid. My husband packed for me, so I saw what he was putting in, but I got to veto, for example, a sundress he chose in favor of a similar one that I liked better.
And I made sure I had a complete bikini, after he tossed two bikini bottoms on the pile without realizing they weren’t a full suit because, “they’re both white.” It just added to the fun and to the surprise feeling – because I wasn’t in the driver’s seat for packing, but I wasn’t totally out of control, either.
And this is another reason to make it a short trip. As I always say, having to pack less means less stress.
5. Take a short, direct flight (or train) leaving in the morning.
We already discussed how a close destination can feel a lot lighter. Specifically, I’d recommend looking for a direct flight (because layovers are a buzz kill, even if you have lounge access) that’s 3 hours or less.
That means you don’t have time to get annoyed by a long travel day.
Tip: You can find all the direct flights from your home airport either using Google Flights (click “Explore Destinations,” then filter for non-stop flights only) or Kayak Explore (enter your home airport, and again, filter for non-stop only).
I prefer Kayak for this because it lets you choose more specific date options, like a trip duration from 3 to 5 days, whereas Google Flights only lets you choose between a weekend trip, or one or two weeks.
And the morning flight? That means you get to actually experience the place immediately when you arrive, instead of finding out where you’re going, landing at 10 PM, and delaying the actual gratification until the next day.
This is another reason why Bermuda makes a perfect mystery trip from the East Coast. I was shocked to learn (once I was already on the plane) that the flight was just 1 hour and 40 minutes from Boston! And before I knew it, I was on the beach for the afternoon.
6. Plan just a couple of things – not too much.
Leave room for exploration. Of course, this is up to you and your person’s travel style. I’d say half the excitement is just exploring a new place without plans or a schedule.
(Of course, if you’re going to Milan, for example, and know your person will want to see the Last Supper, you need to book that ahead of time. So keep in mind if there’s anything like that, but leave room for spontaneity.)
7. But don’t forget the things that really do need to be planned.
This is a short list, because honestly you can go anywhere if you have these things:
- How you’ll get there. (Flight, train, or rental car booked)
- Where you’ll sleep once you’re there. (Hotel, an Airbnb or homestay, or a resort?)
- How you’ll get around. (Will you need a rental car or scooter? Or will public transportation and walking cut it where you’re going?)
- Visas? (This is actually the first thing to check, before you book your travel!)
Related: Here’s my guide to finding more sustainable hotels anywhere.
One final note, if you are going to plan an actual surprise trip, not just a surprise destination:
8. Think about them, not just you.
Make sure you consider whatever your trip recipient has in mind – especially if it’s a surprise birthday trip, or a trip planned around another holiday.
Do they want to spend the actual day with friends or family?
Do they need to request time off work, and if so, how far in advance?
These boring-but-important details are one of the reasons I recommend the mystery trip method above, instead of saying out of the blue, “surprise we’ve got travel plans!!”
How to reveal your surprise trip
A little online sleuthing has shown me that people are very interested in how to actually reveal their surprise trip gift – with a poem, a card, a scavenger hunt, or a series of red envelopes or small gifts that give clues.
We didn’t do any of that and, for the record, I definitely didn’t feel like I missed out.
My husband just told me that it was a direct flight, which was my only requirement anyway. (Because of my experience in sustainability and reducing the climate impact of travel, I try to avoid unnecessary flights whenever possible.)
So our mystery destination was narrowed down by my general idea of where we could fly direct from our current home base. And I avoided doing any extra googling on that topic before the trip – but you know I had been thinking about it for months, and asking him at dinner, “are we going to Iceland for my birthday? Is it the Bahamas?”
He never gave even a glimmer of a hint.
So I had lots of ideas, and just had to guess at the airport. (Which you can watch below.) To me, it was the perfect reveal.
