The Ultimate Family Travel Planning Checklist
Rome, Italy
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Planning a family vacation involves a surprising number of little decisions.
At first, it feels simple: pick somewhere to go, book a flight, find a hotel.
Then suddenly you're comparing rental cars, checking passport expiration dates, making dinner reservations, figuring out whether everyone owns shoes they can actually walk five miles in, and wondering why planning a vacation somehow became its own part-time job.
The good news is that you don't need to plan every minute of your trip.
You just need a system for planning the right things in the right order.
This is the basic checklist I use when planning our trips so I can keep everything organized without making vacation planning more complicated than it needs to be.
1. Set a Realistic Travel Budget
Before you start falling in love with hotels and activities, decide roughly what you're comfortable spending.
You don't need an exact number down to the dollar yet. A realistic range is enough to help you make better decisions as you plan.
Start with the major categories:
Flights or other transportation
Accommodations
Food
Activities and excursions
Transportation at your destination
Parking
Tips
Souvenirs
A little extra for unexpected expenses
One of the easiest ways to overspend on a vacation is to focus only on the big expenses.
A hotel may fit your budget until you add a $50 daily resort fee, $40 parking and breakfast for the entire family.
Knowing your overall budget first makes it much easier to decide what's worth spending more on and where you'd rather save.
2. Choose a Destination That Fits Your Family
There's a difference between a destination being amazing and a destination being amazing for your family right now.
Think about the ages of your kids, how everyone handles travel, how active you want the trip to be and how much work it will take to actually get there.
Consider:
Travel time
Number of flight connections
Time-zone changes
Weather
How easy it is to get around
Activities that fit your kids' ages
Food options
Overall pace of the destination
A twelve-hour travel day might be completely worth it for one trip and absolutely not worth it for another.
You don't have to choose the easiest destination every time. Just make sure you know what you're signing up for before you book it.
3. Decide on Your Travel Dates
Once you have a destination in mind, start looking at dates.
If you have flexibility, compare a few different options before committing. Moving a trip by even a few days can sometimes make a big difference in airfare or hotel availability.
Pay extra attention if you're traveling during:
Spring break
Summer
Thanksgiving
Christmas and New Year's
Holiday weekends
Major events at your destination
If you're tied to a school calendar, you may not have much flexibility—and that's okay. It just means you'll usually want to start planning earlier.
4. Book Your Transportation
For most trips, this is the first major reservation I make once our dates are set.
When comparing flights, don't look at price alone.
I also pay attention to:
Departure time
Arrival time
Number of connections
Length of layovers
Total travel time
Baggage fees
Airport location
That $40-cheaper flight isn't always a deal if it involves waking everyone up at 3:30 a.m., two connections and arriving six hours later.
With kids, convenience has value.
Once your flights are booked, save the confirmation information somewhere you can easily find it later.
5. Book Your Accommodations
Where you stay can have a huge impact on how easy the rest of your vacation feels.
I look at more than just whether the hotel itself is nice.
Think about:
Location
Room size
Sleeping arrangements
Distance from the things you want to do
Parking
Breakfast
Pool or other amenities
Laundry facilities
Resort fees
Cancellation policy
Sometimes paying a little more for a better location saves money elsewhere because you aren't constantly paying for parking, rental cars or rides.
If you're comparing hotels right now, I have a full guide on how to choose the best hotel for a family vacation →.
6. Figure Out How You'll Get Around
It's surprisingly easy to book flights and a hotel and forget about the part in between.
Before you arrive, know how you're getting:
From the airport to your accommodations
Around the destination
To major activities
Back to the airport at the end of the trip
Depending on the destination, that might mean:
Rental car
Public transportation
Hotel shuttle
Taxi or rideshare
Walking
A combination of several options
Also look at parking costs before automatically renting a car. In some cities, the car itself isn't the expensive part—the hotel parking is.
7. Make a Loose Itinerary
This is where I think a lot of people go to one extreme or the other.
Either every minute is scheduled...
or absolutely nothing is planned.
I prefer something in the middle.
Start with your must-do activities and put those on the calendar first. Then build the rest of the trip around them.
I generally aim for one or two main activities each day.
That gives us enough structure that we aren't spending half the vacation deciding what to do, but enough flexibility that we're not constantly rushing to the next thing.
Leave room for:
Pool time
Wandering around
Longer meals
Rest
Unexpected discoveries
Changing your mind
Some of our favorite vacation moments have been things we never planned.
8. Make Reservations for the Things That Matter Most
Not everything needs to be booked in advance.
But if something would genuinely disappoint you to miss, find out whether it needs a reservation.
That might include:
Popular attractions
Tours
Excursions
Shows
Special restaurants
National park reservations
Rental equipment
Transportation
I don't usually reserve every meal because I like having flexibility, but there are definitely destinations where a few dinner reservations can save you from wandering around at 7:00 p.m. with hungry kids while everyone slowly turns against one another.
Book the important things.
Leave the rest flexible.
9. Create a Packing Plan
Packing is much easier when you don't start the night before.
I keep a reusable packing list and adjust it depending on the destination and type of trip.
Start with categories:
Clothing
Shoes
Toiletries
Medications
Electronics
Chargers
Travel documents
Kids' items
Swim or outdoor gear
Carry-on essentials
Then make sure each person has what they actually need.
I also use packing cubes because they make it much easier to keep everyone's clothing organized—especially when we're sharing suitcases.
And always pack your carry-ons separately.
Anything you absolutely need during your travel day should not be buried underneath four pairs of shoes at the bottom of a checked suitcase.
10. Organize Your Travel Information
You should be able to find your important travel information without searching through 47 confirmation emails.
Keep these details together:
Flight information
Hotel reservations
Rental car information
Activity confirmations
Restaurant reservations
Transportation details
Passport information
Travel insurance
Important addresses
Confirmation numbers
I like having everything organized before we leave so I'm not standing at an airport counter searching my inbox for an email from six months ago.
This is also where having one central travel planner makes an enormous difference.
11. Do a Final Check the Week Before You Leave
About a week before the trip, I go through everything one more time.
This is when I:
Check the weather
Confirm reservations
Look for schedule changes
Check passports or IDs
Refill medications
Finish laundry
Start packing
Download entertainment
Charge devices
Make sure we have chargers
Check transportation plans
Take care of anything at home before we leave
None of these things are particularly difficult.
The problem is remembering all of them at the same time.
That's exactly why I created my free Week Before Your Trip Checklist.
Make the Week Before Your Trip Easier
Grab my free Week Before Your Trip Checklist so you can keep track of the little things that are easy to forget before you leave.
12. Prepare for Travel Day
The night before we leave, I try to make the next morning require as little thinking as possible.
That means:
Carry-ons packed
Devices charged
Boarding passes ready
Documents together
Snacks packed
Water bottles ready
Clothes laid out
Transportation confirmed
If we're flying, I also make sure everyone knows what they're responsible for carrying.
Travel days are unpredictable enough without spending twenty minutes looking for someone's headphones while you're supposed to be leaving for the airport.
13. Leave Room for Things to Change
This might be the most important part of the entire checklist.
You can plan everything perfectly and something will still change.
Flights get delayed.
Weather happens.
Someone gets tired.
An attraction isn't nearly as fun as you expected.
You discover somewhere you want to stay longer.
A good travel plan should make your trip easier—not make you feel like you're failing when you don't follow it exactly.
Have a plan.
Then give yourself permission to change it.
Final Thoughts
Planning a family vacation doesn't have to mean months of stress or a 14-page itinerary.
The goal is simply to take care of the important details before you leave so you aren't constantly solving problems once the trip starts.
Set your budget.
Choose a destination that works for your family.
Book the important things.
Create a loose itinerary.
Get organized.
Then go enjoy the trip.
You don't need to plan everything.
You just need to plan the things that make everything else easier.
Want Your Entire Trip Organized in One Place?
This is exactly why I created the Wander With Ease Travel Planner.
It's the same system I use to organize our own trips, with one place for your budget, reservations, itinerary, packing list, and other important travel details.
Instead of confirmation numbers living in your email, your budget living in your Notes app, and your itinerary existing somewhere in a group text, you can keep everything together.