Welcome back to Seldom A Dull Moment! If you’ve made it this far, you’re probably feeling the weight of vacation planning—especially when you’re trying to balance your big kids' disinterest with your desire for a meaningful getaway. If you’re thinking, “How do I get my kids excited about this trip?” or “I’m about to pull my hair out,” don’t worry, you’re not alone.
In the first post of this series, we talked about the importance of dreaming together as a family. But now, it’s time to get to work and design the vacation of your dreams—without the stress, frustration, or feeling like you’re dragging your kids along for the ride.
- Interested in reading the first 2 posts in this series? Click the links below.
Planning a family vacation when your kids are older can feel impossible. “The kids get bored!” “It’s hard to plan a vacation where EVERYONE has fun!” “I give up! No more family vacations!” We've all been there. But the secret to making this work is getting everyone involved—yes, even the teenagers who’d rather be glued to their phones—and designing an itinerary that’s got a little something for everyone. Here’s how to do it without losing your sanity.
Step 1: Picking the Perfect Destination
Let's be honest, choosing a destination that’ll please everyone can feel like an impossible task. But here’s the thing: It’s not about you anymore. Your kids are growing up, and it’s time to start considering what they want too. Sure, you might have your heart set on a quiet beach getaway or a cultural city tour, but your kids are likely thinking, “Why are we going somewhere without Wi-Fi?” So, how do you make this work?
Start by getting everyone in the family to throw out ideas. I mean, really ask them what they want to do. Get the teens involved by asking: “What sounds fun to you?” or “What’s one thing you’ve always wanted to do?” Even if their answer is “nothing,” push for more: “Well, do you want an adventure? Do you want a beach day? A big city? An amusement park?” You get the idea.
By allowing them to have some say in the destination, you’re making them feel heard—and more importantly, invested in the trip. Even if they’re rolling their eyes, they’ll be more excited when they realize they had a part in choosing what to do. And guess what? This isn’t just about them either—it’s about finding a place that allows for different interests. Mix it up: the beach day for relaxation, a theme park for thrills, and a city for some culture. Everyone can get a little of what they want.
Step 2: Deciding on the Duration of the Vacation
Once you've picked the destination, the next question is: How long should the trip be? Now, here's the catch: teenagers do not want to be away from their friends forever. And as parents, you probably want a break from the constant shuffle of school, sports, and work. But how long is enough without feeling like you're on a never-ending road trip?
Here’s where it gets tricky. Have a sit-down conversation with your family. “What do you think? How much time should we spend there?” Some family members might want a shorter trip to fit their busy schedules or energy levels, while others may crave more time to relax. If you’re dealing with grumpy teens, consider a middle ground: a 5-7 day trip is usually the sweet spot.
But, when you’re deciding on the length, it’s important to talk about why everyone wants the time they’re suggesting. Maybe the younger kids want more time at the beach, while the older ones are hoping for something short and sweet so they don’t miss too much of their social lives. Open communication about what each family member wants out of the trip will help find a good balance.
Step 3: Selecting Excursions and Activities
Now, the fun part. Picking activities is often where the frustration hits. You want everyone to enjoy the trip, but your teens might be eyeing their phones, uninterested in “another museum” or “yet another hike.” How do you design an itinerary that actually gets them engaged?
The key is variety. The idea is to find a mix of activities that everyone can get into—without going overboard. After all, no one wants to feel like their vacation is a list of things they have to do. So how do you balance it?
Ask your kids directly about what kind of activities they’d enjoy (or, at least tolerate). Do they want a thrill? Maybe a day at an amusement park or go-kart racing could be the answer. Is relaxation more their style? Maybe you can squeeze in a quiet day at the beach or a lazy day by the pool.
Plan a few activities for family bonding (like a day of sightseeing or a boat tour) but also throw in some downtime. Leave room for a spontaneous activity or two, like visiting a local restaurant or taking an unplanned detour to a cool, quirky spot.
The goal is to design an itinerary that includes everyone—but also gives some breathing room for your teen to Snapchat or take a break from the hustle of family life.
Step 4: Designing the Budget
Designing a budget for your vacation is essential—and it doesn’t have to be a source of stress. Planning ahead allows you to set financial expectations and avoid the dreaded "I need a vacation from our vacation" feeling when you come home to a mountain of debt.
Start by saving specifically for the trip. Having a vacation fund can relieve some of the pressure of figuring out how to afford the fun things you want to do. But here’s the thing: a budget isn’t about rigidity; it’s about creating space for both planned activities and spontaneous fun. Maybe a random ice cream stop turns into the best moment of the whole trip. Maybe an unplanned excursion becomes the highlight.
Leave room for flexibility, so you’re not stressing if you decide to splurge on something last minute. Just remember, the goal is to keep it fun without breaking the bank. Everyone gets what they want (within reason), and you can leave the stress of finances behind.
Step 5: Get Feedback & Finalize the Plan
Now, it’s time to come together as a family again to review everything. Yes, I know, the last thing you might want to do is ask your kids for their feedback—especially if they’ve been dragging their feet up until now. But here's the secret: Getting their feedback and input builds excitement and gives them a sense of ownership in the trip.
Sit down as a family and share the plan. Give them the chance to ask questions or offer ideas. Get their thoughts on the itinerary, and don’t be afraid to make adjustments based on their input. This isn’t just about keeping them entertained; it’s about getting everyone excited and feeling included in the trip.
Remember: flexibility is key. Maybe one kid wants to swap a beach day for a visit to a local amusement park. Maybe another is craving a quieter activity. Listen carefully, and be willing to compromise. You may not get 100% agreement on every detail (and that’s okay!), but the goal is to come to a consensus where everyone feels involved and excited.
From Dreaming to Designing: The Excitement Builds
Designing a family vacation doesn’t have to be a nightmare. When you bring everyone to the table to plan, listen, and compromise, you create a trip everyone can look forward to. You may not please everyone on every little detail, but by getting input and allowing for flexibility, you’ll set the stage for a vacation that’s memorable for all the right reasons.
Stay tuned for the next post in this series, where we’ll cover the final preparations before departure, ensuring that your family is ready to enjoy the trip you’ve all designed together!
Happy vacation designing—your dream trip is closer than you think!
Want more help with your family vacation planning? Want an easy way to engage your "big kids" in the Dreaming, Designing, and Departing process? Order my interactive family vacation planning guide and start to dream and design tomorrow!
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