5 Mistakes Families Always Make When Planning a Trip
Hallstatt, Austria
*This post may contain affiliate links, which means I may earn a small commission if you make a purchase through one of my links, at no additional cost to you. As an Amazon Associate, I earn from qualifying purchases.
Planning a family vacation always sounds fairly simple in the beginning.
Pick a destination. Book a place to stay. Buy the plane tickets. Pack some clothes. Go have fun.
And then somehow you find yourself three days before the trip wondering why the hotel is 45 minutes from everything you want to do, nobody has a swimsuit that fits, and you have somehow scheduled six activities for Tuesday.
Most stressful trips aren't ruined by one huge planning mistake. Usually, it's a handful of smaller decisions that sounded perfectly reasonable at the time.
Here are five of the most common mistakes families make when planning a trip—and what I do instead.
1. Trying to Do Too Much
This is probably the easiest travel-planning trap to fall into.
You've spent the money to get there, you may never visit again, and suddenly everything feels like something you have to see.
So you start adding activities.
And adding.
And adding.
Before you know it, your relaxing family vacation has a schedule more complicated than your normal life.
I usually plan one or two main activities per day and leave room around them. That doesn't mean we sit around doing nothing. It means we have enough flexibility to stay somewhere longer when we're having fun, stop for ice cream, go back to the hotel for a swim, or change plans when everyone is tired.
Especially with kids, downtime isn't wasted vacation time.
Sometimes it's the part that saves the rest of the day.
A good rule of thumb:
Choose your must-do activities first.
Leave some open space in the schedule.
Don't make every meal a reservation.
Build in slower mornings or afternoons.
Accept that you probably won't see everything.
I'd much rather come home wishing we'd had time for one more thing than spend the whole trip telling everyone, “Hurry up, we're late!”
2. Choosing the Wrong Location
A beautiful hotel at a great price isn't necessarily a great deal if you're going to spend half your vacation getting back and forth from it.
Location is one of the things I pay the most attention to when planning a family trip.
Before booking, look at where you'll actually be spending your time. How far is the hotel from the attractions you want to visit? Will you need a rental car? Can you walk anywhere? What does parking cost? How long will airport transportation take?
The same applies to the destination itself.
Think about:
Flight length
Transportation once you arrive
How spread out the area is
Activities available for your kids' ages
Weather during the time you're visiting
The overall pace of the destination
A destination can look amazing on Instagram and still be a terrible fit for your family.
And if you're currently choosing where to stay, I put together a whole guide on how to choose the best hotel for a family vacation, because the nightly rate is only one small piece of that decision.
3. Waiting Too Long to Book
I'm all for being flexible with travel plans.
I'm less enthusiastic about realizing the only hotel rooms left during spring break are either $900 a night or located somewhere that requires a small expedition to reach.
Popular travel dates fill up.
This is especially true for:
Spring break
Summer vacation
Holiday weekends
Christmas and New Year's travel
Popular resorts
Cruises
Destinations with limited lodging
Booking earlier usually gives you more choices—not just better prices.
You may have more room types available, better flight times, more convenient hotels, and a better selection of rental cars.
That said, I don't think you need to book every single detail the minute you decide to travel. Start with the things that are most likely to become expensive or unavailable: transportation and accommodations. Then fill in activities and reservations as the trip gets closer.
4. Packing Without a System
There are two ways last-minute packing usually ends.
You either bring enough clothing to relocate permanently...
or someone arrives without underwear.
I've found that packing becomes dramatically easier once you stop reinventing the process for every trip.
I use a reusable packing list and work through categories instead of wandering around the house throwing things into suitcases as I remember them.
Think:
Clothes
Shoes
Toiletries
Medications
Electronics and chargers
Travel documents
Kids' items
Carry-on essentials
I also like using packing cubes to keep everyone's clothing separated and make it easier to find things once we arrive. They're especially helpful when you're packing several people into the same suitcase.
And pack your carry-ons separately from your checked luggage. Anything you may need during the travel day—or wouldn't want to be without if a suitcase took an unexpected vacation of its own—should stay with you.
The goal isn't to pack perfectly. It's to have a repeatable system so you aren't starting from zero every single time.
5. Not Having a Clear Plan
There's a big difference between not overplanning and not planning at all.
I don't want every vacation scheduled down to the minute. But I also don't want to land somewhere and begin Googling, “How do we get from the airport to the hotel?”
Before we leave, I like to have the important pieces figured out:
Where we're staying
Flight or transportation information
How we're getting from the airport to our accommodations
A few activities we definitely want to do
Any reservations that need to be made ahead of time
A rough idea of what we'll do each day
Confirmation numbers and important travel information in one place
That gives us structure without locking us into a rigid itinerary.
A week before we leave, I also do one final check of everything—reservations, weather, packing, documents, medications, chargers, and all those little details that suddenly become very important the night before a flight.
If you want something you can use for that final check, grab my free Week Before Your Trip Checklist. It's the same kind of reset I use before we leave so I'm not lying in bed wondering whether I forgot something.
Final Thoughts
A good family vacation doesn't require a perfect itinerary.
You don't need to predict every possible problem, plan every meal six months in advance, or create a color-coded schedule that requires its own orientation meeting.
You just need enough of the important pieces figured out that you can actually enjoy yourself once you get there.
Give yourself some breathing room. Choose a location that makes sense. Book the important things early. Create a packing system you can reuse. And keep your trip information somewhere you can actually find it.
The goal isn't more planning.
It's better planning so you can think about it less once the vacation starts.
Want Everything Organized in One Place?
This is exactly why I created the Wander With Ease Travel Planner.
It's built around the same way I plan my own trips, with one place to keep your budget, reservations, itinerary, packing list, and other trip details organized without turning vacation planning into another full-time job.