The Ultimate Surprise Holiday with Surprise Trips

by Brenna Holeman


“What are you up to this weekend?” Mike, another regular at my local pub, asked me over a pint.

“I’m going on holiday,” I replied, taking a sip of my beer.

“Lucky you,” he smiled. “Where are you going?”

“That’s the thing,” I responded, smiling back. “I have absolutely no idea.”


I’ve always dreamed of planning a surprise trip for someone. I can’t imagine anything more fun than secretly booking a holiday, planning the flights, hotels, and activities all while the other person has zero clue what’s going on or where we’re going. I’ve always thought that the absolute coolest thing I could do for someone is to say, “I have our weekend planned. Pack a small bag, and bring your passport. Meet me at Heathrow at 5pm this Friday”… all mysterious like I’m James Bond or something (how James Bond always looks so stylish when he travels on a whim, I will never know. Does he take a travel-sized iron with him? Get dry cleaning at the hotel? I’m rambling, I’ll move on).

On the flip side, if someone ever did this for me… oh my. I would take that person straight to the chapel and marry them, because, as mentioned before, it is THE ABSOLUTE COOLEST THING. A spontaneous holiday? Not knowing where you’re going until you get to the airport?! For me, someone who loves spontaneity and adventure, I can’t imagine something more fun.

And then, as if they could read my thoughts, along came Surprise Trips. Because Surprise Trips does exactly that.


Surprise! We’re on an airplane, flying to… wait, where are we going again?

The premise behind Surprise Trips is this: they plan a surprise holiday for you, booking your flights and hotel to a mystery  destination in Europe. A few days before you’re set to depart, you get a weather update, so you know what to pack. And then, the day of your departure, you arrive at the airport at the designated time, and… you get an email telling you where you’re going. To reiterate: you have no idea where you’re travelling to until you get to the airport. When they approached me and asked if I’d like to be one of their guinea pigs – the idea only came to fruition this summer – I couldn’t contain my excitement. (Full disclosure: I work for the company that hosts Surprise Trips, though I don’t work on Surprise Trips itself. Despite that, I would never post anything but an absolutely genuine and honest review on my blog, so please know that all opinions are my own.)

I asked my friend Jen if she’d like to tag along, and she was also game. As the date of our departure loomed closer, we started to look at the possible destinations – all 77 of them – and wonder where we might be going. Even as someone who works in travel (and who plays way too many online geography quizzes for her own good), there were many destinations I barely knew anything about: Trondheim, Caen, Limoges. This made it all the more exciting to me… just where the hell were we going?! I had given Surprise Trips a few cities I didn’t want to go to – you’re allowed to exclude some cities from the list – mainly because I had been within the last year (Stockholm, Aarhus, Madrid).

When we got the weather report a few days before, we knew it would be fairly warm, from the mid to the high 20s. As this was July, that narrowed our guesses down to… well, it barely narrowed it down at all. We were up for anything, though, whether that was Italy, Iceland, or anywhere in between.

On the Friday morning of our departure, Jen and I headed to Stansted Airport for 9:45am. Surprise Trips emails you exactly two hours before your flight, so you have to have a smartphone or device with working internet/4G in order to check it. We tried not to look at the board of departures, because we wanted it to be the ultimate surprise. Hovering around the departure gates, we finally got the email… that told us were were going to Prague for the weekend!


I honestly couldn’t have been happier – Prague is a city I first fell in love with ten years ago, and I had been aching to go back ever since I moved to London. I’ll be writing a post all about what to do in Prague on a long weekend very soon (including my best photos from the city).

I was also very happy with how everything worked out with our Surprise Trip. Our flights were booked for reasonable times, meaning we left early enough on Friday to still enjoy most of the day in Prague, and, returning that Sunday, our flight wasn’t so late that we missed the last trains back to London. Our hotel was standard, but clean and comfortable, and it was in an absolutely amazing location (three minutes from Charles Bridge). Overall, we had an absolutely fantastic weekend, and it was made even more special by the fact that we had no idea where were going until we got to the airport.


Bit of a moody selfie overlooking Charles Bridge

Some notes on Surprise Trips:

-Right now, Surprise Trips only books holidays that fly from the UK or Ireland.

-All final destinations are European, and no flight is longer than 3.5 hours.

-What you pay (you decide how much you want to spend on your trip… I imagine that the more you spend, the farther you go and/or the better quality your hotel) covers your flight and your hotel, but nothing else.

-Surprise Trips can be booked if you have a UK, IE, CA, AUS, NZ, US, or EU (Schengen) passport, and you can designate if you’d like to travel to a Schengen country to avoid a potential visa issue.

-All airlines used are those that allow you to walk up to the departure desk and check in, meaning airlines like Ryanair – which charges you if you don’t have your boarding pass printed before you arrive at the airport – are excluded. No need to worry about printing boarding passes.

-As many airlines charge to check baggage, it is recommended to pack carry-on only, as Surprise Trips does not pay for excess baggage.

-Because you’ll be checking in only two hours before your flight, there is a chance that you won’t be sitting with your travel companion on the airplane. In our case, Jen and I were seated one row apart, and as it was a short flight, it was no big deal.

-For more, including a fun video, check out their site.


First beers in Prague

So is a Surprise Trip right for you? I think this type of holiday is ideal for a couple or small group of friends (the maximum amount of people per booking is four, and all travellers must be over 18… but I believe child-friendly options are coming). You have to be fairly adventurous and laid-back; if you absolutely must stay in a luxury resort when you travel, for example, you might not like that you don’t have control over your hotel booking. You also obviously won’t be able to do any research about the place you’re going to, but in today’s age, I find that “things to do” lists are only a Google search away, and you’ll have some time before your flight to do a wee bit of research or buy a guidebook in the airport. Finally, you have to have a bit of flexibility with your budget, as even though your hotel and flights will be paid for beforehand, prices can vary quite a bit across Europe.

All in all, I think a Surprise Trip is perfect for someone who wants to shake things up a bit and have a bit of an adventure; I also imagine this would be ideal for a birthday or celebration of some kind, like an anniversary.

And would I take another Surprise Trip? Absolutely, in a heartbeat. I thought it was such a fun idea, and I loved the spontaneity and excitement I felt before going. It was exhilarating to show up in a place without anything planned; I’m not much of a planner anyway, but this took it to a whole other level. And do I still think that having a surprise holiday planned for you is THE ABSOLUTE COOLEST THING? Yes, 100%, and I can’t wait to do it again.


Thank you very much to Surprise Trips for hosting me in Prague. While they covered my flight and hotel, I paid for the rest, including all ground transportation and food. As always, all opinions are my own. 

Would you go on a Surprise Trip?

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Louise Terranova October 11, 2016 - 11:54 pm

What fun. Are they always weekend trips? Nice selfie with the bridge behind.

Brenna Holeman October 11, 2016 - 11:58 pm

No, I believe you can choose any dates you want! And thank you 🙂

Jasilyn October 12, 2016 - 6:47 am

I’ve wanted to do something like this, but no one flies from Russia. 🙁 🙁 🙁

My boyfriend wants to go to Prague though, and I heard it’s an amazing city! It’s good to hear you weren’t disappointed to go there again!

Brenna Holeman October 12, 2016 - 10:23 am

Yes, Prague is so cool! I hope you get there soon 😀

Danielle October 12, 2016 - 7:42 am

Sounds like so much fun! I recently booked a trip to Edinburgh for my friend’s birthday and she had no idea. Getting her to open a big shiny envelope with the destination inside at the airport was so fun! I live for European city breaks, so I’d need a few more than 3 excluded cities Haha!

Surprise Trips October 12, 2016 - 10:00 am

Hey Danielle! You can actually exclude as many destinations as we want, but we just recommend to choose three to keep it spontaneous :-)!

Brenna Holeman October 12, 2016 - 10:21 am

Oh great, thanks for the update! I’ll change the post to reflect it.

Brenna Holeman October 12, 2016 - 10:22 am

Aw, that sounds amazing Danielle! What a cool idea. It turns out I was wrong, you can exclude as many cities as you want! 😉

Tom Matuschak October 12, 2016 - 11:51 am

Brenna I love reading you newsletters about travel. The latest is not exception. I was a bit concerned when I saw you posted a picture of your boarding pass. Recently there has been many articles why you shouldn’t post pictures of your boarding pass in the news because the bar code stores personal information about you. Search ” you shouldn’t post your boarding pass online” to read the articles.

Brenna Holeman October 12, 2016 - 11:56 am

Hi Tom, thanks for your concern! I’ve also read those articles and some have said that it isn’t true, so I took a chance. You’re right, though, I shouldn’t have it online. 😀

Katie October 12, 2016 - 12:49 pm

Now I want to live in Europe even more! This looks like so much fun. I think my only concern would be packing… even though they give you the temp, you might dress very differently in Andalusia than you would in Rome or the Vatican. Still, just for a weekend? I could get over myself. The more I think about it, the more I am madly in love with this idea!

Brenna Holeman October 12, 2016 - 3:05 pm

I’m madly in love with it, too! I really hope I get to do it again… and yes, you should move to Europe! 😉

Paige October 12, 2016 - 1:15 pm

This idea would totally get me out of my comfort zone, as I love to plan and buy my tickets and guidebooks early *cough* may have already bought tickets for big solo adventure #2 for next summer *cough* BUT I really love this idea regardless! So glad they give a weather update–when I first started reading the post was wondering how one would know what to pack. You’re so right though, with the Internet, learning plenty to have an amazing trip can be done at the airport. So looking forward to your Prague post–the city is very high on my list!

Brenna Holeman October 12, 2016 - 3:09 pm

It really does get you out of your comfort zone, but for a few days, I think it’s quite manageable, even for those who like to plan a year ahead ;). And yes, I hope to get the Prague post up very soon… those city guide posts always take me a very long time to research/write/etc!

jessica October 12, 2016 - 2:22 pm

My husband’s birthday tradition is to watching the hot dog eating contest at Coney Island every year on the 4th of July, so I planned a surprise trip to NY for us to go watch it last year. I didn’t quite make it to the airport before I told him, but it was one of our favorite vacations of all time anyway! Surprise trips are wonderful 🙂

Brenna Holeman October 12, 2016 - 3:04 pm

Aw, that’s an incredible gift! I’m so glad it worked out. 🙂

Kate October 12, 2016 - 2:25 pm

I love this idea – what a fun way to travel! Now that I’m living in the UK I’ll have to check this out!

Brenna Holeman October 12, 2016 - 3:03 pm

I definitely recommend it!

Elina October 12, 2016 - 2:27 pm

Oh my gosh, this is the best thing I’ve read today! I met a Dutch girl last summer who told about a similar company in the Netherlands and I was so bummed there were no options in the UK. I had no clue this existed! Cheers, Brenna, you might have juts solved my problem of what to get my boyfriend for Christmas…

Brenna Holeman October 12, 2016 - 3:03 pm

Oh, that’s amazing! I really hope that you do it, it’s so much fun…

Korii October 12, 2016 - 2:31 pm

What a cool idea! I think it’d be a great way to get you out of your comfort zone when travelling and taking you to places you might not have ever considered! I will have to see if there’s anything similar here in Australia, although I imagine it might be a bit difficult to do surprise trips here, given the size of the country!!

Brenna Holeman October 12, 2016 - 3:04 pm

Yes, definitely, it gets you out of your comfort zone! Thanks for the comment, Korii 😀

Nina Lee: World into Words October 12, 2016 - 4:22 pm

What an incredible idea! I would totally go on it, though, man it would take some serious effort on my part as a slight control freak. But I think it’d be an awesome chance to push myself outside of my comfort zone and really have a great adventure. I hope they eventually set it up to fly outside of other countries (*coughSpain*)!

Brenna Holeman October 12, 2016 - 4:42 pm

Yes, it certainly brings you out of your comfort zone, but as most people would only do a short city break, I think it’s totally manageable! I hope they start flying from other countries soon, too. 🙂

Tash October 12, 2016 - 5:51 pm

This looks amazing! I’m now trying to convince lots of people to do this with me.

Booked a surprise trip to Krakow for my boyfriend’s birthday last year, booked it months in advance but had to give away the fact that we were going somewhere as he got invited on a stag do the same weekend!

Brenna Holeman October 12, 2016 - 8:25 pm

Aw… I’m sure he was still so surprised! I hope you get to try one of the trips 🙂

Danny October 12, 2016 - 10:15 pm

This reminds me a lot of the Blind Booking option with Germanwings and Lufthansa Surprise. The only difference is that you select a category (party, beach, culture, food, etc.) and then you find out where you’re headed right after paying (of course, you determine the exact dates and can also “strike” cities from the list). So if you’re ever looking for a way to do a surprise trip out of Germany…

Brenna Holeman October 13, 2016 - 12:43 pm

Oh, that sounds cool! Thanks for letting me know. 🙂

Ruth October 14, 2016 - 9:25 am

My brother arranged a surprise trip for my (now) sister-in-law on the Orient Express to Venice and it was on this trip that eh proposed! Such a great idea, in fact I can’t believe he actually pulled off all of the organising, he’s usually terrible at that kind of stuff!

Brenna Holeman October 14, 2016 - 4:22 pm

Oh wow, that’s so amazing!! What a surprise…

Rebecca October 15, 2016 - 3:37 pm

SO MUCH FUN!! I would love to do this – need to find a company that does this sort of trip from my part of the world! 🙂

Brenna Holeman October 17, 2016 - 11:29 am

It was indeed so much fun! I hope you get to try it 😀

Steven October 17, 2016 - 4:46 am

Having birthday surprise on Prague? It must be one of most unforgettable memory for u,, Its make me curious on how we feel if friends or someone close to us make a secret trip.. may be i should try it once in my life and i wonder which destination should be picked.

Brenna Holeman October 17, 2016 - 11:28 am

It wasn’t my birthday, but it was still a really wonderful surprise!

Suze - Luxury Columnist October 17, 2016 - 4:34 pm

What a brilliant idea, I love surprises! Sounds like it turned out very nicely with your Prague trip

Brenna Holeman October 17, 2016 - 4:51 pm

Yes, it was fantastic! I definitely recommend it.

Jolene October 18, 2016 - 5:27 am

This truly sounds ridiculously wonderful! I struggle most in deciding where to go so this would be perfect! What a wonderful way to travel!

Brenna Holeman October 18, 2016 - 10:45 am

Yes, isn’t it fun? I would definitely do it again!

Heather October 28, 2016 - 7:52 pm

What a great idea! I’ll have to look into this 🙂
In other news, I’ve been thinking about planning a surprise trip for my husband. Not totally a surprise since he needs to request the time off of work. Then again, I’m friends with others at his work so I might be able to get one of them to help request the time off. Hmmm….

Brenna Holeman November 11, 2016 - 2:20 am

I hope that it works out for you! 🙂

Zalie November 27, 2016 - 7:37 am

I love this idea! I wish Canadian airlines could make this happen!

Brenna Holeman November 27, 2016 - 3:12 pm

Come to Europe sister… 😉


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