Are surprise trips a good idea?

Of the millions of miles I’ve flown, my most memorable trip ever had to be the one I took with my mom the summer after I graduated from high school. We went to Australia and New Zealand, and not only is New Zealand probably the most beautiful place I’ve ever been, but we had a lot of fun as well. And I actually love traveling with my parents — they couldn’t be more supportive of what I do, and when I first told them I wanted to do “my own thing” after college they were more convinced in it than I was, and that’s despite the fact that my dad doesn’t even know how to turn on a computer, much less know what a “blog” is. If you ever meet my dad and want some quality entertainment, ask him what I do.

Anyway, sadly I haven’t been able to travel with my parents the past few years as much as I’d like to. They own a small business that requires them to open and close it every day, so taking trips is for the most part off the table. That being said, my mom has a big milestone birthday coming up next month, which may or may not be similar in number to one of my favorite Kuala Lumpur clothing stores. šŸ˜‰

She has worked her ass off and deserves a trip, and I’m scrambling to figure out where to take her. While she says she just wants to go to Germany, she has never been to Asia before, so I’m really thinking I should take her there, or somewhere else she hasn’t been.

But the one thing I’m dying to do — and I’m trying to figure out whether this is a good idea or not — is make this a surprise trip. I’m sure we’ve all had the desire to do this at some point. Book a trip for a loved one and tell them to show up at the airport without knowing where they’re going. On one hand it seems exciting for both parties involved, but I wonder, does that actually maximize the happiness derived from a trip?

I’ve read plenty of articles saying that the most happiness derived from a trip comes from the anticipation as opposed to the trip itself. Is that taken away or increased when it’s a surprise?

And for that matter, where the heck should I take her? I should have probably planned this a year out.

PS: Mom, if you’re reading this, the post is obviously a joke. I planned this trip a year out and everything is set in stone, and I’m just posting this to throw you off. Yeah, let’s go with that.

Filed Under: Advice, Travel
  1. I don’t enjoy surprise trips. I want to be in control of when and where I travel, or at least be a 50/50 contributor in the decision making process. I also need time to mentally prepare myself for a long trip. Much of my enjoyment of traveling comes from researching the possibilities and planning an itinerary. Having someone just suddenly show up and whisk me away to the airport would be hard for me to stomach and would be difficult to schedule with my employer. That being said, I have taken someone else on a “surprise” trip before and they seemed to enjoy it. I think this is the sort of thing the average girl probably enjoys a lot more than the average guy.

  2. My fiancee at the time (eleven years ago this month) wanted to be surprised for our honeymoon, so just to get my bearings, I asked if she preferred mountains or beach and north or south. Once she answered those questions, I planned the rest. She was very happy with the destination as she had some very limited input, but we spent our honeymoon in the Canadian Rockies and are still married today.

  3. My Partner and I are taking away my mom this summer for a 12-day European adventure. I am glad we did not surprise my mom as hearing her excitement every time she calls about the trip and having her plan things that she is really excited about, makes this all worthwhile. I think you will love the back and forth with your mom about all the great things you will see and do! You’re a good son!

  4. Fully dependent on the person you’re surprising, and their personality.

    Is your Mom the type of person that would show up for a surprise birthday party and be excited to see her friends and family? Or would she act happy but really be upset she didn’t get a chance to dress nicely, get her hair done, etc?

    If she’s adventurous, spontaneous, and not a control freak (like I am), I think it would be a great thing to do!

  5. I actually love traveling with my parents and taking them out for trips, given how much they’ve given and how hard they’ve worked.

    That said, it depends on your parents’ personality and you know more about theirs than any of us here.

    For my parents, we did a very special trip for their milestone birthdays, and it was the happiest vacation enjoyed by all. It was a vacation a year in the planning. They took the time off, have time to plan, have some time to anticipate the hotels we will be staying in, and figure out what they think they want to do.

    I wouldn’t have it any other way, except to maybe shorten the planning time to less than half a year. The anticipation of waiting a year was crazy, but it gave me enough time to use miles/points wisely, upgrade our flights, and plan itinerary.

    So no, unless you’re planning to travel domestically, surprise trips are definitely NOT for everyone!

  6. You guys should go to Hong Kong or another place in Asia and then surprise her by stopping in Germany on the way back. Maybe Asiana to Hong Kong and then LH all the way back, in first of course.

  7. If you do decide to surprise her, give her some advice about climate, and what kinds of clothes to pack, unless part of the surprise is a shopping splurge at your first stop.

  8. Only surprise trip I’ve been a part of was a bachelor party cruise for a friend of mine. Naturally, it was very well received. He didn’t know at all that he was going on a cruise until we pulled up to the dock.

    That said, I don’t think most circumstances call for a surprise trip. Much like an elaborate show you put on to propose to a girl, sometimes you should just let the moment (or trip) speak for itself.

    If your parents are exceptionally open minded and flexible, then the unplanned, unknown could be great. If they like to have a plan of what they want to see and do, then probably not so much.

  9. The best trip my wife and I have ever had was when I surprised her with a long weekend in NYC. We had only been out of college a year and hadn’t even begun to think of the points deal, but I had her pack what I thought was appropriate and she found out when we got to the airport. It was great! I would definitely recommend the surprise. I am moving with my family to England in August and plan on doing last minute discount trips for weekends wherever we can find great deals. Places of course that would be worthwhile, but still. Surprise her, but make sure it’s a place she would want to go and not just a place you want her to go.

  10. I actually thought about this for a while. I travel quite often, so the idea of someone taking me on a surprise trip sounds wonderful! It would be such a nice break from all of meticulous planning that I usually do-to have someone care enough to do the planning for me sounds lovely. But the key to the way I feel is that a surprise trip would be a *break* in planning. I love planning trips, and the anticipation of leaving really is the best part. If your mom doesn’t travel often (as you say) then gifting her the planning phase might be the better route to take, since it’s something she can’t usually indulge herself with that part. But also, I’ll have to agree with the other commenters and say that it really does depend on the recipient’s personality and how open she is to the surprise. Either way, your mom is a pretty lucky lady!!

  11. Surprise trips are not as good for the recipient as they are for the giver. Better, in my experience, to let her know where, when and for how long, but fill the actual trip with surprises. Give her the macro ahead of time, wow her daily with the micro.

  12. If your mom likes dressing up and price is of no object, then you might consider taking her on a cruise on Hapag-Lloyd’s Europa, possibly the world’s best cruise ship. That way the environment is German, while visiting areas of the world that might be new to her. You’d have to forego the surprise aspect as she’d need to know what to pack.

  13. Presumably visas would need to be considered – or would you have her apply for multiple ones as they do on the Amazing Race?

  14. Take your mom to Japan. I just took my wife there on a surprise trip a few weeks ago. First time for both of us. Had a great time and as a German, I appreciated how efficient, clean, and safe it was (we were in Tokyo).

  15. Asia and Middle East on the same trip would be amazing. Both very exotic and at the same time very different for someone that never been there. Also, hotels are amazing. Only problem with a surprise trip is that it has to be to a place where visa is not required otherwise it would not be a surprise.

  16. mangoMan said,

    Take your mom to Japan. I appreciated how efficient, clean, and safe it was (we were in Tokyo).

    I hear Chernobyl is even cleaner and safer than Tokyo. I’m sure it’s just a matter of time before the Ukraine starts building resorts from which to watch millions of freakishly deformed birds.

  17. As someone who runs an entire company based on surprise trips, I think they’re fantastic, but I’ve gotten so many reactions to this question! About half of people think it’s great and would love to go, and the other half thinks we’re completely crazy and can’t even fathom why someone would want to pay us to plan a trip for them and not give them the details.

  18. Take her to tanz/kenya for the migration in june. Go via fra(stopover). The hotair balloon is an incredible vantage point. Luxury lodge choices abound.

  19. As a top place to see I’d say Hong Kong, but it’s a terrible idea in the summer. No offense to the other posters, it was my first thought as well, then the weather issues hit me.

    Japan or Singapore would be the obvious choices. Interesting, civilized, easy to reach. Can’t think of many exciting places with pleasant weather in June in Asia. Bali would be another, but it adds another flight.

    Nothing in the CN Traveler April Grand Tour of Asia strikes you as interesting for your mother? Granted most of the places are ones that you’d have to visit in northern winter.

  20. Don’t surprise her as how will she know what to pack, etc?

    I think @Usairelite hit it spot on with Hong Kong and a stop in Germany. (Or maybe Singapore with a stop in Germany.)

  21. I planned a suprise trip years ago for my otherhalf as a birthday suprise. What I did was order one of those photobooks you can create online in a “this is your life” format… I included dates/pictures from the past (birth, 1st day of school etc) and the last 2 pages basically said “and this weekend you’re flying to…” and the next page was a picture of Disney World and I attached the 2 plane tickets and amusement park tickets. Satisfied my desire to Suprise with the trip but also gave 2 days of excitement and knowledge of what to pack etc… best of both worlds

  22. How about Scandinavia? Couple of days in CPH and ARN and a road trip to Geiranger fjord from BGO. Or event better Road trip to Lofoten islands from EVE.

  23. After the discussion about press trips and free travel on Gary’s blog today, perhaps you change the first sentence,
    “Of the millions of miles Iā€™m flown” :).

  24. My turn to chime in:
    1) IMO I think people roll with everything much better when they are younger -including surprise trips. As we age we become more set in our ways. I would hasten to guess that your parents are less spontaneous than you and thus I would lean towards letting them know about the trip.
    2) You and your parents may have different likes so I suggest planning out two trips -one which focuses in and around Germany and one which focuses in a couple places in Asia. Have them review your mock itineraries (countries/cities to visit) and allow them to decide -even if it is a combination or both.
    3) However, I agree with dubaych, once your general idea is agreed upon allow them to give specifics about what they want to do and see if they will agree to give you the liberty to add on your own specific ideas -since traveling is your expertise.
    4) Remember you are planning this for them and you want them to really enjoy it and break free from their everyday responsibilities.

  25. I think you’re right in asking the question because not everyone appreciates the spontaneity of travel like we do. My sisters and I surprised my parents with a trip to Italy for their anniversary, and the initial trip was just 4 weeks out…my parents FREAKED! They loved it and appreciated it, but I guess people in their 50’s just don’t enjoy the last minute rush of picking up and flying to another country. To some people, this would be a dream come true. To others, this would be a nightmare. Everyone is different.

  26. Florianopolis, or wherever it is in Brazil that has all those German expats. For bonus points, fly there on *A.

  27. I have a family member who loves surprises. I think it makes him feel powerful, but it is really annoying to be treated as though my time and thoughts do not matter. So obviously I would very much urge you not to make it a surprise. In my opinion, it would be so much more respectful and loving to solicit her thoughts on where she would most like to go and find out what is convenient for her in timing. Remember the trip is about her! Also, I think you are absolutely right to be thinking about the lost happiness from the anticipation. That really is a huge amount of the happiness derived from much of life and definitely travel.But how wonderful you have such a great relationship and are looking to really do something special for her!

  28. You know your mom best and whether or not she would like a surprise. I am too much of a control freak to want a total surprise, but would be happy if the destination was announced a tiny bit ahead of time so I could pack, look up the place, etc. I think no matter what happens, your mom will have a great birthday!

  29. In the end, I guess it really depends on your Mom – you’re the only one here who knows her well enough to make the call. Some folks enjoy, even thrive on exploring the unknown and just rolling with the punches, while others could be annoyed or even terrified by such a trip. In any case, a Happy Birthday to your Mom and I’m sure you’ll have a grand trip.

  30. I’ve tried to surprise my parents but realize now that what tgey say is what they want. I may think dinner at Smith & Wollensky for steak is good for them but they want Longhorn and see no reason for more expensive place. We now go to longhorn and they are happy.
    If your mom wants to go to Germany and specifically said that than I’d go with that (love the cruise suggestion) unless she expressed an interest in somewhere else.
    are you doing what is best for her or what you think is best? the good intentions are there either way and am sure it will be great birthday trip

  31. Why not do a combination of both? Start it as a surprise destination and then agree on a certain time you will tell her where. Right now I’m in my room at the Park Hyatt Buenos Aires(old section). Thismwasmgoing to be a surprise for my husband. Just told him to block out the dates for his big birthday. I was so excited about the surprise, but I screwed up and forgot the hotel confirmation would go to his email. Oh we’ll. we’re having a fabulous time. Off to Rio tomorrow

  32. I decided to “surprise” my almost-4 son with a trip to Disneyworld years ago. We drove three hours to the airport (to take advantage of an $80 RT flight), and he was too young to know what was going on. We got to the airport and I told him we were getting on a plane and going to DISNEYWORLD! He did NOT want to get on the plane.

    We ended up having a good time, but he needed time to process. I realize it’s different with adults — to some extent.

  33. My husband surprised me for our tenth wedding anniversary. He said we were going to Singapore and Bangkok. We ended up in Rome then boarding a Mediterranean cruise. A small luxury ship. I had NOTHING to wear! I was pissed for about 10 hours, but got over it. I will also say, I wished that I was involved in the planning because it definitely makes the trip more fulfilling.

    We are taking my mom on a cruise for a big birthday this September. She is bringing a friend and they are so excited! Shopping for clothes, planning excursions! Tell your mom!

  34. In my experience “surprising” parents or older generations isn’t such a great idea unless they really love such unexpected changes. In my experience, they like to know where they are going so there are no surprises. I would only surprise her with a trip to Germany, because she knows people there and it isn’t stressful to go there for her. That way if it is an F experience for example, it is all about the trip and how you managed to get her in F etc. What a great kid to do that for his mom! I would definitely not surprise her with an exotic locale which could potentially create a lot of stress and push the boundaries of their comfort level at such a time. Just because you think it would be cool doesn’t mean they would like it.

  35. Does she like the act of flying as much as you, or what is at the end it? I know my mom wouldn’t want to be a place a day or two and then in the air again, and something tells me this trip is going to be a week or so. Granted my mom is a little older.

    I assume the possible surprise part is the destination and not the fact that the trip is happening. If so you may be able to guage her reaction if you say the destination will be a surprise.

    If the the thought is the trip happening at all is a surprise then I’d say NO and let her enjoy telling everybody her son is taking her on a trip.

    Don’t dismiss Germany just because it wouldn’t be your choice.

  36. As a guy you may not totally appreciate how crucial this is, so please just trust me. If you decide to make it a total surprise, may I suggest being very, very specific and informative in letting her know enough to pack properly. I was once taken on a surprise weekend getaway and told to “pack as if for Vegas.” Actual trip was to San Francisco. Well, regardless of time of year there is almost always at least a 30-degree temperature difference between the two, and walking around a hilly town requires different shoes than sitting at a casino and watching Cirque de Soleil shows all day. Thankfully it was only for a weekend, and I appreciated the gesture and (hopefully) did not come off as ungrateful, but would have enjoyed the trip much more had I been properly prepared.

  37. This is funny. We’re in the same planning process, but our mother is a decade younger and doesn’t care for global travel. We would love to whisk her off some where, but every time we hint at a far and away place she quickly dismisses it. She just wants her brand name watch and she’ll be more than content. We may just have to settle for her wish and perhaps plan something later.

    Happy planning and we hope it works out for you.

  38. I had a surprise honeymoon trip given to me by my now ex husband. Luckily I had a friend who was a travel agent that did all the leg work for a fantastic holiday in Fiji many years ago. I knew I had to pack summer clothes for a beach location. I have sprung surprise Disneyland/Hawaii trips on my teen daughter. When she was younger I didnt tell her we were going away until about 2 weeks before…she nearly cried when she found out – she just loves Disneyland Anaheim so much. I think the best surprise I ever pulled on her was the trip where she thought we were flying UA Y SYD LAX because our upgrades had not cleared despite being booked 9 months in advance. In fact, since it was so hopeless getting Y to C upgrades cleared out of SYD, a fluke offered me a chance to jump on an F (A Fare) upsell about 3 weeks prior to our departure. So I bit the bullet and took the F class with 1A and 1K seats for us. Daughter had NO idea we were flying first class and was thinking we were in Y (and still hoping for C upgrades to clear). I think I finally told her once we were in the car going to the airport. She would have suspected once we checked in at the F class line. It goes without saying she LOVED it šŸ™‚

  39. EDIT: Actually now I remember….I walked up to F class check in with her and that’s when she knew! SO excited. Good luck with what you decide with your Mom. I think as we get older we do become less appreciative of “surprises”. My Mom freaked when I arranged a surprise 60th Birthday and got her friends from life and work (current and past) and best friend from another state to attend, without her knowing. She was so overwhelmed it took the fun out of it for her. Lets say I learned my lesson and will NEVER do another surprise event like that for her again. Let us know what you do decide šŸ™‚

  40. If your mom says “Germany” do NOT surprise her with Asia! Maybe mix in Austria instead.

    Just sayin….

  41. Lucky, I seldom pull the age card but trust an old guy on this. Don’t surprise her. Plan the trip she wants with her and add delightful things she wouldn’t know about for the surprise.

    Children love surprises. But for parents, most surprises frankly aren’t that pleasant. We pretend they are because we don’t want the kids to feel they disappointed us, but just trust me on this, if your Mom says Germany, she wants Germany.

    Where you can surprise her is a private tour of something that interests her, or a truly great dinner out at a restaurant with relatives or friends she hasn’t seen for a long time, or a professional photographer to document an outing, or the best seats at a concert.

    I surprised my mother on a trip she planned and wanted to take by setting up a private appointment with a perfumier who developed a signature scent. It was something she never would have done but loved. My siblings were grateful since they would restock for all gift occasions. Another time I surprised my dad at a planned golf game by playing with a PGA pro he liked. (I knew the guy’s wife.) Parents like those types of things but trips to Hong Kong when we wanted Germany, not so much.

    Well, you did ask…

  42. From my own experiences, I think most women want to know what to pack. Surprises are fun, but I hate it when I don’t know exactly what I need to bring! Also, if it’s longer than just a weekend getaway, it might be more fun for you & your mom to plan things together šŸ™‚

  43. I surprised my fiancee with a trip to Germany to propose. She thought she was coming to Houston (long distance) for just a couple days, but I had her parents send some clothes and her passport to me, and we went straight back to the airport. I even had a refundable ticket for her back home to cover my tracks. She loved the surprise, and I think it made everything that much better. Definitely make sure that you’ve covered things like packing, etc. though.

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