A few years back, my then 5 year-old mentioned that a friend at school went on a family surprise trip to Disneyland and one of my kids asked if we’d do the same thing for them.  Like I’ve mentioned on other pages, I really enjoy planning trips and planning surprise trips for kids is even better.


Our first opportunity came when my mom tried to get the whole family to go on an Alaskan Cruise for her and my dad’s 50 wedding anniversary.  There wasn’t a whole lot of interest from the rest of the family even though our family of 4 thought it sounded great.  I knew my mom really wanted to go and as our kids were getting older, the time for Grandma Time was now.  With that, Jill and I decided to take an Alaskan cruise and invite my mom.


Planning a cruise is really pretty easy.  Just pick the itinerary, the date, and search for the best prices.  We booked our airfare to Seattle then chose to wait until relatively close to the departure date for the best pricing.  Our flights were compatible with several cruise lines with similar itineraries.  This left us fairly confident that we wouldn’t miss the boat so to speak.  If you can be flexible and don’t care about your cabin location, you can get some killer deals if you wait until the last minute.  In the end, we were able to get 2 rooms next to each other for a decent price.


Packing is clearly Jill’s area of expertise.  When we got close to the departure day, Jill would quietly sneak a pair of the kids’ shorts here and a shirt there until we had everything we needed for both kids.  She was even able to get some special stuffed animals and other treats without them ever noticing.  In the end, were able to get everything into a few roller carry-ons and one bigger suitcase.  This all sat in our closet and the kids never noticed.

The Art of Deception

A few weeks before the trip, I started the story that I needed to go to Seattle for work.  I had recently presented at a work conference so I just piggybacked on that to say I needed to do it again in Seattle.  The cover worked well and when we left to “Drop off Dad” at the airport, it helped to explain all the suitcases.  Dad needed lots of computers and electronics for the presentation.  I even convinced them that I had gotten gate passes so they could come down to the gate.


Boarding started and we did the obligatory hugs and kisses goodbye.  I started collecting the carry-ons, paused and said “How about if you come with me?”  They both looked at me with that “Yeah, right dad” look so I said it again.  “Really? You’re kidding right?”  I looked at Jill then back to the kids, “Surprise”.  They couldn’t believe it, they were so excited to be going to Seattle and had no idea what else laid ahead.


We did normal tourist activities in Seattle and were having a great time.  The kids were so excited to be on their surprise trip but were tired of walking and getting hungry.  Jill convinced the kids to just sit on a bench for a few minutes to people watch when all of a sudden, Eli says “Hey, that looks just like Grandma.  Wait, it IS Grandma!!!”.  Surprise!!!

Cruise Time

The next morning, we decided to go for a walk along the harbor while we secretly sent Grandma to the pier with the luggage.  We turned the corner and the ship came into view.  The kids’ eyes lit up again when they saw the size of the ship.  Jeremy even asked to take a cruise for our next vacation.  Ha!  I told the kids I had an idea and told them to wait a minute.  I ran ahead to meet my mom and the luggage to turn it over to the cruise line.  When I returned I told them I arranged a tour of the ship and lunch aboard but we had to be off the ship by 3:00 when they set sail.  Again, they were in awe.

During the check-in process, Jill and I kept looking at each other in disbelief that the kids were not catching on to the prank.  We even got our picture taken while boarding and the kids bought it all.  We did the “tour” and even checked out our rooms.  The kids just kept saying how we have got to take a cruise some time.  We casually ate lunch and were later sitting up on the deck eating an ice cream cone when the boat started moving.  Jeremy FREAKED out!  “Call the Captain!!!!  Call the Captain!!!!  We’re not supposed to be here!!”  Then Eli, “Our luggage is over there!!!  We don’t have our stuff!!!”  Jill and I just looked at the kids and said “Surprise.”

They couldn’t believe that they were going to spend a night on the cruise ship and were even more amazed when they learned it would be 7.  The kids didn’t even care where they were going.  They never even asked but when we told them it was Alaska, the grins almost wrapped around their head.

In the end, we all had a great trip and the quality time with Grandma was priceless.  There were many more “Surprise” moments as we took various excursions but the look on the kids’ faces as the boat was pulling away was something I’ll never forget.

If you’re up for the challenge, plan a surprise trip for your kids or grandkids.  I guarantee you won’t regret it.