The Deal Mommy

My #1 Tip for Traveling With a Teenage Boy

Traveling with a teenage boy means taking your photo opps when you can get them.

Deal Kid consented to a rare photo with his mom with a new old-school Fuji instant camera. 

I’ve been traveling with the Deal Kids since before Deal Kid was born. True story- Deal Kid would have earned BA status if we could have figured out how to get his flights credited in utero.  Now Deal Girl is ten and Deal Kid is thirteen- a full blown teenager. Traveling with a teenage boy is in some ways more challenging than traveling with a toddler. Yes, there’s less poop, but there are just as many ways to step in it. 

With younger kids my #1 tip is to minimize transitions. I offer this tip for both logistical and sanity-saving reasons. With older kids you don’t have to worry as much about moving around. There’s less stuff to haul and they’re more prepared for change. However, even if the kid is taller than you are (as Deal Kid is at thirteen), remember that you’re still dealing with a kid. 

My #1 Tip for Traveling With a Teenage Boy

As I’m typing I realize there’s probably a listicle hidden in here but I’m not gonna give in. I have a number of examples from this past weekend to share but they all add up to one piece of advice: meet him where he is. 

Meet him where he is? What on earth does that mean?

I’ll explain. This weekend Deal Kid and I took a Mother-Son press trip to The Condado Plaza Hilton in San Juan, Puerto Rico. The theme of the trip was “Family Fun at the Condado” and the hotel delivers in spades: 

Snorkeling and Kayaking- both offered right there on property- are what I call “big fun”. So is ziplining at Toro Verde Nature park, especially when you do it horizontally like Superman:

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I conquered La Bestia-the beast! #familyfunatcondado #tmom #hosted

A post shared by Dia (@thedealmommyblog) on

However, where Deal Kid was- and where I met him- was wrapped up in the “small fun”. Stuff like scratching the 8 ball at pool. Like taking a best of three Ping Pong tournament to 25 points.

Traveling with a teenage boy: Deal Kid ponders his next move.

Deal Kid ponders his next move.


Or destroying me in lawn chess. And of course enjoying a double scoop of coconut ice cream at 11PM at Cafe Caribe.  So what that we were stuffed from flourless chocolate cake from dinner? 

Fortunately the Condado excelled at the small fun, too. 

While my first choice for a Saturday night in San Juan might not have been Pokemon Go hunting, I have to admit we had a lot of fun!  PokeStop treasure collecting across the footbridge to Fort Geronimo’s ruins was just the right amount of exercise after our fresh sushi dinner. 

What “meet him where he is”  doesn’t mean:

He doesn’t get to be a jerk! If “where he is” at the moment is torturing his sister and doing the human equivalent of flinging his feces I’ve still got to shut it down. That was one reason I really enjoyed this weekend with him- one on one the kids just aren’t tempted to stray from their best selves as much. 

Since my kid is just entering the teenage years I’d love to hear from those of you who have graduated- does my advice track with most boys or just my boy? Is traveling with a teenage girl much different? Traveling with Deal Girl as a teen will be different but Deal Girl is a much different person. Please share your thoughts in the comments. 

The Deal Mommy is a proud member of the Saverocity network. 

My #1 tip for traveling with a teenage boy.

2 thoughts on “My #1 Tip for Traveling With a Teenage Boy

  1. Lela, Frugal Nellie

    Love your photos and post, Dia!

    My deal kid just turned 12 and looks so very very much like your deal kid! Though my son would probably prefer the superman zip-lining of all the fun stuff you listed! Maybe some day we will all cross paths. For now our travel is temporarily grounded until family finances are re-arranged into better order, but we will get there soon! Someday I dream of house-swapping in Europe for extended summer living!

    1. thedealmommy Post author

      Thanks, Nellie. One thing I’ve learned is that once you get there staying longer is actually no more expensive than staying for a week or two. Monthly rentals (or even exchanges) can be more cost effective than even a week at hotels. Hope you can get out there soon!

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