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!

Big Fun in the Little City: Fort Wayne, Indiana

Clickbait City

Not long ago a clickbait-type ad surfaced on my Facebook feed, suggesting I click through to learn all about a dynamic cultural urban powerhouse emerging in an unlikely city stuck inexorably in flyover country.  Well, I’m living here in the great American midwest, and given my goal to find great things for teens to get into no matter where they roam, I, um, clicked.  For my readers’ sake, I wanted to discover just where this magical midwestern metropolis could be.

Much Ado about Much!

This special city ended up being Fort Wayne, Indiana, population 264,000.  As it happens, an old friend lives there and had recently invited us to visit and enjoy one of his band’s live music gigs.  Who could say no to catching up, savoring some classic, live tunes and getting away for an overnight with the world’s best daughter?  Looking forward to confirming any and all claims from the aforementioned clickbait, my daughter, Holland, and I planned to stuff as much activity into our 24-hour sojourn in Fort Wayne as we could.  Should you ever find yourself with the occasion to visit this charming city, I hope Holland’s travelog below helps you discover some of the fun to be had!

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Seven Top-Rated Road Trip Activities for Teens

Boring road trip coming up?  Not if I have anything to say about it!  (And I do!  Read on!)

Airline seatback entertainment
Fun aircraft seatback entertainment

Flying from Dallas to Atlanta?  Sailing from Memphis to Cincinnati?  Summer vacations are all about the road trip.  Even flying to a fun destination necessitates getting from point A to point B via car, train, donkey, or rowboat!

Enduring the time spent to get to your ultimate vacation spot can cause much joy or much frustration for you, but especially for your teens.  The electronic babysitters game gadgets you’ve relied upon for years may let you and your family down if they run out of juice in the middle of a lengthy voyage.

board game road trip

Under the circumstances, you’ll want to be sure to bring something analog to keep your youngster entertained.  But we’re talking about teens, here.  They’ve been enjoying their highly interactive digital treats for years!  How in the world will anything non-electronic do?

Continue reading “Seven Top-Rated Road Trip Activities for Teens”

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