How to Give a Surprise Vacation Trip

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Christmas is done – whew!  It sure was a good one here, and I hope it was for you, too.  I really love giving fun or slightly over-the-top gifts from time to time, and this year two of those gifts I gave were surprise trips! There’s plenty of research out there that an experience, such as travel, is more meaningful and remembered long after the excitement of a material possession wears off.  There’s also no question that many of us have more than enough “stuff” in our houses, so giving a great gift without adding to the “stuff pile” is a definite win.  Plus, let’s be honest, it’s also super fun to put together a travel surprise that someone might not do for themselves, and then go on the trip with them!

Giving a Surprise Trip

The Magic of Christmas Morning

However, giving a trip as a surprise can be a bit complicated, so I’ll tell you how I did it in case you want to do something similar for a friend or family member in the future.

1.  Be 100% sure of the gift receiver’s travel preferences and schedule.  I would argue that if you can’t be 100% sure of whether the gift recipient will like the destination and be free to go that you should probably not book the trip before telling them about it as it just isn’t worth the risk and stress.  You can still surprise them with the idea of the trip, but I would not make the actual bookings (or at least not any non-refundable portions) if you don’t know the recipient and their availability well enough to be pretty certain that they will be both jazzed and available.

2.  Don’t put their frequent flyer info into the booking.  The easiest way to have your secret plan foiled is to have the trip show up in the recipient’s email inbox or frequent flyer account.  This will almost invariably happen if you put their frequent flyer number in the reservation.  This sounds like an easy step to skip, but be aware it can happen without you even intending for it to if you have booked a trip for them before and they are already a traveler in your airline account.

For example, I booked trips for both my mom and my husband for Christmas and both were already travelers in my United account.  I had to enter them as new travelers in order to not have their frequent flyer number default into the reservation.  The system then tried to override them into a known traveler since the names were the same, so I had to get a little creative with entering middle initials vs. middle names.  In the end it worked, and now that Christmas has passed I have gone back and put in their United frequent flyer numbers and known traveler numbers.  There is a chance this will throw off your ability to use Pre-Check or similar, so there is a potential slight downside to this form of trickery.

3.  Don’t use their miles or points.  This one should be pretty obvious, but don’t use someones miles or points to book their surprise trip for various reasons, including they are likely to see the activity in their account or email inbox.

4.  Consider gift certificates if you aren’t 100% sure of their travel preferences.  One thing we have done for some extended family members in the past is give airline gift cards if we know they like to travel, but we aren’t in a position to know exactly when and where they want to head.  We have found that this is an especially good gift for grandparents who have grandchildren spread around the country.

5.  Wrap it up in a creative way.  The gift of travel is good enough that it doesn’t have to be dressed up in fancy wrapping in order to be awesome, but if you are like me, it is fun to come up with a unique way for the recipient to find out about the gift.  For example, give a trip to Paris in a box of macarons, or a ski trip in a box of fake snow, or in our case a trip to Spain using a huge map that your mom used in her high school Spanish classroom for 30+ years.

It isn’t totally necessary, but it sure builds up the fun and excitement for everyone in the room as you can see by our trip reveal to my mom on Christmas morning!

Giving the gift of a vacation may be a bit more risky than a sweater, DVD, or cozy blanket, but it can also be way more fun.  If you have ever given a surprise trip, then I’d love to hear what you did and how you did it!






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  1. Love it! I did this for a friend once and it worked so well that I ended up starting a whole company for surprise trips, Magical Mystery Tours. No matter how many trips we do, I always LOVE the anticipation and of seeing people’s reactions to a new destination (plus, we’ve done it enough that we feel pretty certain that we can zero in on places that travelers will love!)

  2. This is cool, Spain is a great destination. My brother used to live there and longs to go back. I have tried to tell him how to get there easily and he blows me off.

  3. I gave my husband a surprise trip to Las Vegas the weekend of his birthday. We lived in Michigan and his birthday is in the middle of February. It was so cool because I had already told him to be completely available that weekend and I packed his suitcase without him knowing. My mother flew in from NYC (where we’re originally from) the morning of to watch our son, and we jumped in the car and left. He thought we were headed to a Casino he mentioned in downtown Detroit. He was so shocked when we ended up at DTW airport and I made him check into his flight airport code LAS. Definitely the best and most unforgettable gift I’ve ever given.

  4. We gave my parents a trip to New Orleans for this Christmas but I chose to tell them in advance because of planning logistics. They also have a SW companion pass so at some point I needed to get them involved in the planning. I also needed to transfer Club Carlson points to my dad so he could book 2 for 1 under his name. We still got them to open an actual present on Christmas Day and it was a gift card for them to have extra spending money on their trip.

  5. My 13 year old loves Lemurs and talks about them all of the time. Her main Christmas present is to be able to attend the Lemur Science camp at Duke University next summer for a week.(we are in Wisconsin)There is a nearby cat.1 Hyatt that will help make the trip more affordable. I laminated the logo for the camp and wrapped it up several times for the surprise. Definitely cheaper than a family trip to Madagascar.

  6. I planned earlier this year a surprised trip for my husband to go to New Orleans after Christmas this month to celebrate his upcoming big birthday! My kids chipped in their ideas, and his niece is flying in to watch my kids! I did all the bookings using Delta miles to fly first class on Alaska, booked two nights using Club Carlson credit card BOGO benefit before its devaluation, found a crazy deal on Travelpony for Hyatt French Quarter for about $120 a night! I even created a new open table account just so I can reserve New Year’s Eve dinner!! Even though he didn’t believe me that we would be home for Xmas, he was really surprised when we presented him the surprise trip over Thanksgiving with a box containing an Alaska Airline model plane, a Cafe Du Monde beignet mix, a bottle of creole seasoning and several oyster shells! All those goodies I have to ask my friend to buy through her Amazon account so he couldn’t see it in ours! Mileage accounts aren’t the issue as he never looks at them. We leave in 10 days!

  7. My daughter gave us a trip to Mendocino, California. The first package we opened was a customized viewfinder which had different images of the inns and activities she had planned. The next gift were the actual gift cards along with a letter detailing recommended activities and restaurants.

  8. My husband planned our honeymoon last year. I knew he was planning the trip but he did not tell me where we were going. I didn’t know until we were sitting on the plane and the Captain announced our destination! He had all the travel documents and every time we had to say where we were headed or anything he would just show the papers, I’m sure they thought we were crazy but it was worth it. He had me bring earbud along and listen to music or play games on my phone while we waited so I wouldn’t hear announcements or look at the schedule boards. We went to the Bahamas and it was the best trip I’ve ever been on!

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