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- Issue #11: How to Vacation With Teenagers in 2025 (Without Losing Your Sanity or WiFi Signal)
Issue #11: How to Vacation With Teenagers in 2025 (Without Losing Your Sanity or WiFi Signal)
The First Rule of H.M.C - Don’t Talk About the H.M.C
Welcome back!
The First Rule of H.M.C - Don’t Talk About the H.M.C
What’s on Today’s Agenda:
🍔 Damn, That Looks Good
🩳 2025 Swim Trunks
🎧 New Song
🏝️ How to Vacation With Teenagers in 2025
🤣 Dad Joke
👀 Must-Watch Documentary
💪 He-Man Life Lessons
Damn, That Looks Good 🍡
@chadtyson checking in from #camp where we decided to made #blackstone #twinkies today! #camping #camper #blackstonegriddle #dessert #grilling #grill... See more
Your Wardrobe: The Best Men’s Swim Trunks for 2025
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Listen To This Album At Your Next HangOut💿
How to Vacation With Teenagers in 2025 (Without Losing Your Sanity or WiFi Signal)

How to Vacation With Teenagers in 2025 (Without Losing Your Sanity or WiFi Signal)
Teen vacations used to be sitcom material. Eye rolls. Hoodie hibernation. Mysterious aversions to sunscreen. But in 2025, you’ve got tools. The chaos can work in your favor when you adjust your game plan.
Here’s your no-fluff playbook for vacationing with teens and making it count.
1. Give Them Skin in the Game
This isn’t your solo show. Your teenager doesn’t want to be dragged along on a perfectly choreographed dad itinerary. Pull them in early.
Call a family planning huddle. Let each teen pitch one must-do activity. Make it competitive. Treat it like Shark Tank.
If someone wants to hit a vintage arcade, they’ve gotta sign off on the sunrise hike too. That’s how vacation democracy works.
📍Dad Tip: Use Google Docs or the Notes app to build a shared itinerary. Drop in “choose-your-own-adventure” slots. Keeps the energy collaborative instead of combative.
2. Accept the Phone is Part of the Trip
Teens and tech are one unit. Their phones hold friends, playlists, maps, cameras, and an entire social universe. Take the WiFi needs seriously.
Instead of fighting it, build in scroll time. Schedule downtime where they can plug in without guilt. Say something like, “3 to 5 is cabin chill time. Do what you want.” It removes the constant tug-of-war.
📍Dad Tip: Prep offline content ahead of time. Download Spotify playlists, offline Google Maps, and a few games. Spotty signal will sabotage your peace faster than a forgotten charger.
3. Anchor Each Day With One Plan
Pick one solid activity each day. That’s your anchor. Everything else flows around it.
Go for a morning trail, then open up the afternoon for rest. Plan a late-night fire pit with s’mores and speakers. Build in breathing room so teens don’t feel overbooked.
📍Pro Move: Let them sleep in at least once. You’re building memories, not running a boot camp.
4. Go Where Teens Can Roam
Choose destinations that allow freedom and safe adventure. You don’t need a theme park. You need a spot with open space, decent food, and some chill factor.
Here are a few dad-tested winners:
Hocking Hills, OH – Cliffs, caves, and just enough signal to check Snapchat.
Nashville, TN – Music, murals, hot chicken, and vintage shops.
Montreal, QC – Feels international, speaks some English, serves poutine.
Sleeping Bear Dunes, MI – Water, sand, trails, and quiet evenings.
Look for lakes, walkable towns, and anything near good tacos. Teens do better near snacks and nature.
5. Make Food the Main Event
Food solves everything. Hunger trumps mood swings. If you want buy-in, feed them early and often.
Turn meals into mini missions. Find that ridiculous diner. Do a dessert tour. Let them pick the pizza toppings. Play music while you cook together at the Airbnb.
📍Dad Tip: Plan for one “no rules” meal. They pick. You pay. Fries count as a vegetable.
6. Use the Car for Connection
Long drives create rare space. Eye contact becomes optional. Conversations unfold between snack breaks and playlist battles.
Bring a “Would You Rather” deck. Let them play DJ. Ask about their music. Tell a story from when you were fifteen. Pick a weird one.
📍Bonus Challenge: Build a shared road trip playlist. Add songs as you go. Let it become the sound of the trip.
7. Give Them Room to Disappear
Teens need space. Let them take solo walks, sip coffee on their own, or retreat to their room with their earbuds for a bit. No need to hover.
When they step away, don’t panic. Let them breathe. Let yourself breathe, too.
8. Make Memories Easy to Catch
Some teens live on camera. Others keep things closer to the vest. Give them low-pressure ways to record the trip.
Ideas that actually work:
Disposable camera or Polaroid they control
Family Instagram takeover
Private group chat with daily pics or inside jokes
Short videos or voice notes for a recap reel
📍Dad Tip: Snap candid photos instead of staging them. Everyone looks better when they’re not being told to smile.
9. Add a Game to the Journey
Throw in a playful challenge. Keep the fun low-stakes and weird.
Try one of these:
Weirdest souvenir wins a milkshake.
License plate hunt on highways.
Street food taste test with scores.
Photo scavenger hunt around a new town.
Structure doesn’t have to feel like rules. Just make it silly.
10. Talk About It Before You Unpack
Last night of the trip or somewhere on the drive home, open the floor. Ask what they liked. Ask what annoyed them. Ask if they'd do it again.
Keep it light. Keep it real. Get a few laughs out of it.
Let them know their input matters. That this wasn’t just a dad show with a guest list.
One Final Thing
Travel with teens requires patience, snacks, music, and curiosity. You’re not curating a highlight reel. You’re giving your kid a memory that lasts longer than the trip.
They might not say thank you right away. That’s okay. You’ll see it in the stories they tell later.
Pack your hoodie. Charge the chargers. Book the thing.
You’ve got this.
Try Out This Dad Joke At Work
What do you call a boomerang that won't come back? A stick.
👀 Must-Watch Documentary
The Mask You Live In is a documentary that explores how cultural expectations around masculinity affect boys' and men’s mental health in America. It follows real boys and young men as they try to make sense of what it means to “be a man” in a world that often rewards silence, toughness, and emotional distance.
Through personal stories and expert insights, the film shows how media, peer pressure, and even well-meaning adults push boys to hide their emotions and avoid vulnerability. That pressure creates real consequences for their relationships, self-worth, and mental health.
The documentary presents some tough truths. Boys in the U.S. are more likely to face behavioral challenges, fall behind in school, and become involved in violent situations. The film links these patterns to early exposure to rigid masculine ideals, sometimes starting as young as age 12.
To learn more, visit IMDB.


