Teens’ Secrets to Planning the Best Vacation Ever

Struggling with how to please your teenage son or daughter in any endeavor, not just vacation planning?  I know that feeling well!  There’s just something about this time in a youngster’s life between childhood and adulthood that challenges any parent.

This entire website is dedicated to fun teen travel to and within various destinations, of course, but with the help of my teen daughter, Holly, I wanted to provide some all-encompassing tips for your family travel planning — no matter where you go or what you wish to accomplish.

Holly has already been to three countries and most every corner of the U.S.  She’s done mission trips, road trips with just her mom, multigenerational family excursions, a sailing or two, and the usual school outings.  If you’re like me, you want to have every tool in your trip planning arsenaI available to enjoy travel with your teen.  They will be busy with college and work before you know it!

Given the wanderlust she inherited from me, Holly was perfectly suited to compile a wealth of tips for parents to consider when planning and executing a fun family vacation, Totally Teen Travel style!  I hope you and your family can make good use of these tips (and acompanying convenience items)!


Teen clothes shopping

  • I love a brand-new wardrobe before vacation.  It makes me feel fresh and confident.
  • Road trip snacks are everything. Period.
  • The middle seat is always the worst seat on an airplane. Aisle seats are best for easy restroom access and window seats are for the view.
  • Comfy road trips are the best. Always remember blankets, pillows, and especially hoodies.

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  • A cold car is always better than a hot car.
  • Museums are great for teenagers, but think twice before taking a teen to a little kids’ museum or a museum that’s paragraph after paragraph of text.
  • Teens are awkward, insecure, and anxious, so please avoid big crowds.

Crowds Vacation Planning

  • Sometimes the coolest attractions are the most obscure. (Example: Glass blowing is so much fun to watch and way relaxing)
  • There should be at least one day on a vacation where everything is up in the air. Like a no-plans day where you can explore the place and do stuff on the go.

  • Stick to local restaurants with a signature style of food. It’s nice to order something in to a hotel room, but do focus on trying to get the taste of the city.

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  • Just because something is cell phone related doesn’t mean a teen is gonna love it.  Focus on their interests, like hobbies or sports.
  • Anything that a teen’s favorite celebrity, band or athlete is associated with, they’ll love it.
  • Live performances, concerts, plays, and musicals are everything.

  • Sometimes teens just want to run off and explore places.
  • I myself love to spend money on vacation, because I know very soon I’ll have to be really careful with my money paying bills and any school tuition.

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  • Homesickness is always going to occur.  It’s best just to let a teen mope for a hot second.
  • It’s really reassuring to at least know someone before going to a place so they can help with directions, tips, and suggestions.
  • Teens like to overpack because we want to make sure everything will go as planned.

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  • Scenic places are the best to just have a day and relax, like camping in the woods or sunbathing at the beach.
  • The best public pools have water slides and diving boards.

  • Vacationing during school is risky… even if your teen looks relaxed, they’re probably stressing over all the work they’re missing.

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  • It’s always nice to have a way to know the state of the house while on vacation, like a house-sitter or nanny cam, to make sure everything is okay and any pets are well fed.

Teen and Dog Vacation Planning

  • Schedules help a lot.  Teens (including myself) have a hard time remembering everything like times and dates.

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  • Replicas are cool, but the real deal (if available to the public) is always the way to go.
  • When at a hotel, teens enjoy their own bed to stretch out and roll around care-free at night.
  • It’s always fun to do little things on vacation that normally isn’t done at home like get ice cream out, or go to parks or go to bookstores.

  • There shouldn’t be any regulations to how much food can be eaten or how much sleep can be slept.  Vacations are a break away from daily life.
  • Quarter machines are much more fun than they may seem.  The satisfaction of getting a random object is really cool.
  • Vending machines are always great, but the only problem is there are too many options…

vending machine vacation planning

  • Summer equals no dress codes.  Go crop tops, spaghetti straps and sleeveless shirts!

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  • If at all possible, don’t take me any place with an overabundance of little children.
  • Gum.

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Do you or your teens agree with this list?  What would you add to it?  Let me know in the comments!

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