How to Plan a Trip with Kids, Without a Travel Agent

Are you in the early planning (or dreaming!) stage for a trip with a baby, toddler, or kids, but you’re not sure what to do next? Is this your first trip with dependents and you’re feeling a little lost about how to plan?

I’d love to give you some tips!

This is the system that I use, and it might not be exactly right for you, but I’m hoping that my trip planning routine can help inspire and give you confidence if you’re feeling stuck in the process.

I’ve never used the services of a travel agent, and honestly – maybe I’m missing out! But I actually really love to plan our trips DIY-style, and I am good at it.

I’m in the middle of this process myself, planning a trip for our family to Israel and Malta in less than a month. So I’m living this right now!

The wanderlust stage

This is the first part of the process, and it usually starts for me as we’re on our way home from our last trip. It probably drives my husband crazy!

This is where I start saying things like, “I just want to travel forever!” and “Where are we going to go next?” and push my husband to consider jumping on the digital nomad bandwagon.

No luck on that one yet!

In this stage, I start to think about where we haven’t been, what’s been hot lately (I’m looking at you, Game of Thrones filming locations!), and I spend a lot of time scrolling Pinterest and daydreaming.

I usually end up with a shortlisted-bucketlist (is that a thing?) to keep in mind until we’re ready to set a date.

The initial planning

This is where we start to talk about dates. We look at my upcoming breaks at work (I’m a teacher, so these are predictable), compare this against times that may be a little more calm at my husband’s job, and nail down a time frame.

When possible, we try to leave this loose. 3 weeks in late summer is much easier to work with than having a specific set of dates at this point in planning.

This is not always possible, especially working around school breaks. If we’ve only got 1 week for Spring Break, there’s no wiggle room!

Once we have a time frame, I look at my top list of destinations and think about which ones are best for that time of year. This is huge, and something that people often forget! Maybe we’re not going to the place that I’m most excited about, but we’ll go someplace that matches the time that we’re traveling best.

The location double-check

Okay, we’ve got a time frame, and we’ve chosen a location that I’ve been wanderlusting over and that works well at that time of year. Great!

Now I spend some time looking more closely at that location. Sure, it looks great on Instagram, but if we’re going to plan a trip there, I need to know more about it.

This is where I start reading travel blogs. I look for the experiences of people with kids (and babies if I’m lucky enough to find that!). What did they do? What did they love? What challenges did they face?

I search for the top things to do on Google or TripAdvisor, and scroll through the lists. I know the kinds of things that I like to see when I travel, and I’m looking for a good amount of attractions that jump out at me as something I definitely want to do.

I’ve ruled places out because most of the top 20 attractions were museums or historical buildings. Not my jam when traveling with a toddler! I’m sure those places still had lots of awesome off-the-beaten-path things to do, but when traveling with littles, I want to focus my time on places that offer a lot of the type of travel activities that we love.

It’s usually at this stage that I “present” the place to my husband. I am 100% the planner for our trips, which frankly is ideal for both of us. Before I get any farther in the planning, I run the location by my husband. I show him the coolest attractions and some basic expectations about the place.

Maybe this is a weird step, but since I plan everything with minimal involvement from him, this gives him a chance to see what I’m planning and get excited. He could, of course, veto at this point – but he doesn’t. He knows I’ll plan an awesome trip wherever we go!

The organization

At this point, it’s time to get organized for all the work to come. I’ve always preferred to use OneNote for this. I like the ease of copy-pasting information and itineraries, it’s super easy to add screenshots which can be very helpful, and it makes it a breeze to access all of the planning from my past trips.

I always create a new notebook for each trip, and then create the key pages: Agenda, Flights & Lodging, Things to Do, Major Costs, etc.

Maybe you’re more into bullet journals, or binders, or word documents, or whatever. But you’re going to want some sort of system!

The flight search

This is where it goes from fun and inspiring to tedious and frustrating.

It has always been very important to me to spend wisely on our vacations. We travel hack. We often stay in AirBnBs. We avoid checking bags as much as possible.

And we find the best value on flights that we can.

When it was just the 2 of us, I would have instead said we find the cheapest flights that we can, but that’s no longer true. Traveling with a baby and a toddler, we care more about the airline and flight time than we used to.

But there are still ways to save a LOT of money on flights – if you’re willing to put in a little time!

My personal favorite way to look at flights is to simply use Google Flights. They pull data from all the major sources, and have all the features that I love. I know a lot of regular travelers swear by SkyScanner or Hopper (which I used to love, but feel it lost functionality).

Scott’s Cheap Flights is an amazing resource for finding dirt-cheap flights, but only if you’re willing to be flexible with when and where you travel to (or have the time to wait for a deal to your specific location).

Tip #1: Use an Incognito window.

Start by opening an Incognito window. Why? If you’re still planning and looking around at multiple dates/options, you’re going to be doing several flight searches. And you know what? The prices will increase. Looking at flights repeatedly tells the algorithm that you’re serious about booking something, so – of course – the price will jump up.

This happened to me just the other day looking at our flights. I searched once (of course in Incognito), played around with some settings, and then came back to do that first search again. It was $200 more the second time.

Searching in Incognito mode deletes your browsing history, so the next time you open a new window – you’re back to the original price.

Tip #2: Look at the flexible date graph.

This won’t work if you have very tight, specific dates. But if your dates are flexible, be sure to check out the date graph. This is a feature in Google Flights, but also in other sites like Kayak (you have to add the +-3 days filter to the dates), Expedia, etc.

I’m always drawn to the happy, green numbers showing the lowest cost dates to fly, but they’re not necessarily going to be the ones that work best. Maybe the second lowest number is actually a much better flight. Be sure you spend some time playing around with this feature!

Tip #3: Be realistic about flying with little ones.

I want to save money when we fly, of course, but I also want to maintain my sanity. Really think about what is going to work for your family! Is it worth saving $100 per person to add an extra 4 hours of travel time? You will probably end up asking yourself that kind of question a lot.

I will no longer consider flights with more than one stop, unless absolutely necessary. 2+ stop flights don’t usually save you that much money anyway, and the airport transfer is a highly stressful time. Not worth it.

The big question that parents flying with a baby of toddler for the first time always ask: is it better to fly during the day or take a red-eye?

Get ready for my awesome answer here… who knows?!

Every experienced parent traveler has an opinion about this, but there is no consensus. That’s because every kid, every age and stage, and every flight is different.

I’ve had marvelous success with red-eyes. Except that one time that my 22-month-old decided to stay up for the whole 10 hours, ruining the first 2 days of our trip as she reeled from the jet lag.

I’ve also had great success with day-time flights, but that’s not perfect either. If your toddler is used to running around and playing during this time, it’s tough to keep them happy in an airplane seat for hours on end.

Think about your kid, your comfort level with potentially having a disastrous red-eye, and book what seems best for you. You can’t predict how it will go, anyway.

Once I have a good idea of the flights that I want, I add them to the OneNote but I don’t book them yet. Unless the trip is under a month away, in which case time is of the essence!

Oh, and what about that whole “Tuesday is the cheapest day to book flights” thing? I have honestly not found this to be the case, and I’ve seen reports lately that Sunday is actually the cheapest now. In my experience, assuming you’re not booking last minute and you use Incognito browsers, the prices tend to stay the same or vary by only a few dollars throughout the week.

This is not the case if you’ve found an awesome sale fare – don’t let that pass!

Narrowing down the specific locations

Back when I was in the wanderlust stage, I was looking at the location as a whole country or region. Maybe I was looking at a specific city, but we never stay in just one place when we travel.

It’s time to figure out exactly where we want to be, and how much time we want to stay there.

This is where you might want to revisit the top attractions that appealed to you before. Are they all close enough together that you know right where you need to stay? Or are they spread around? Will you need to move throughout the region during your trip?

For example, on our upcoming trip, we will be staying in Tel Aviv, and most of the attractions we have planned are there. But we would be remiss if we didn’t spend a few days in Jerusalem, so I’ve been narrowing down which nights to stay in each city.

This is also when you’ll want to figure out exactly how you will get from place to place. Do you need to rent a car? Catch the train? Uber or taxi? Hop a short flight? This might impact your choices.

Once I know roughly how long I want to be in each area or city, I roughly sketch it into my OneNote. I still want to be flexible at this point, although I might be starting to see some things that require us to be in a certain place on a certain day – special events, farmer’s markets that happen once a week, a performance we’d like to catch, etc. I make sure those are marked on my agenda.

The lodging search

This stage can be really easy or a lot of work, depending on the type of traveler you are.

I really love to stay in AirBnBs. I also really love to find especially unique, or quintessentially local AirBnBs. This is another place where I spend a lot of time playing with the dates, and this is why I did not set in stone any of my plans in the previous step.

If you put in set dates, you will only see what is available for those dates. But maybe if you flex the dates a bit, you might find the coolest little chateau or the most beautiful penthouse! I always try different combinations.

If you are someone who just wants to spend the whole trip at the same hotel or resort – great! This step will be easy for you!

If, like us, you like to spread your time between different cities, different AirBnBs, maybe a hotel here or there – this is where you can get lost hunting for the perfect combination.

Keep track of everything, take lots of notes, and compare prices as you go! You might save some money by staying AirBnB on the weekend, and resort mid-week, for example.

Time to book the big stuff

Now that I’ve figured out the best flights, I know when and where I want to stay, how I am going to get from place to place, and I’ve found the perfect lodging: I’m ready to book.

Get back into that Incognito window and go for it! I always start with flights first, because they are the biggest and most nerve-wracking purchase. I also like the peace-of-mind of having 24 hours to cancel without penalty if I’m using Expedia!

Get everything booked at once, and get all of the details down in your notebook.

Yay! The hard part is done!

Build an agenda

This is where it starts to get fun again. Using Pinterest, TripAdvisor, my favorite travel blogs, and good ole Google, I make a list of all the things that I’d like to do if I had all the time to do it. This includes the sites I want to visit, but also specific events. I link everything in my OneNote for later.

I like to give this one a little time. Add to this list over the course of a week or two. I find that I’m inspired to look for different types of activities at different times, and I want to have a full, well-rounded list here.

Once I’ve got a hefty list, I’m ready to create my agenda.

For me, I like to have a table-view of each day of the trip, with room to fill in the main activity for the day. A calendar would be great, too, though I personally don’t like to include all of this in my Google Calendar.

I start by blocking out the flights and any moves between cities. Then I put any time-sensitive attractions down, then the things that are at the top of my list of Things to Do.

I don’t fill up every moment of the calendar. Particularly at the very beginning of the trip. Traveling with kids – especially little ones – can be unpredictable. I leave at least every third day blank, because I know there will be times that one of our major plans didn’t work out, and we’ll need a make-up day.

But I will still have lots of things on my Things to Do list that aren’t on the agenda, so if I do manage to keep up with the schedule, I will just choose one of those activities for the day.

If any of the activities on the agenda require advance booking, I go ahead and do that now. If it’s something that could be booked just a day in advance, I will often wait until we’re on the trip to book it, when we have a better idea if everything is working out how it is supposed to.

Phew! That’s it! Easy, right? 😉

Now sit back, relax, and daydream about your trip. Nothing to stress about until you’re ready to pack.

---

What kind of traveler are you? Do you like to DIY, or do you hire a travel agent? Let me know why in the comments!