Planes, trains, and automobiles! Ever since I was a kid, I’ve loved to travel. Each year for my birthday, I’d ask for a Rand McNally Atlas. I logistically helped my parents plan our family trips. I also dreamed about places that I’d visit once I was fully in charge! I’ve been fortunate to make many of my travel dreams come true.

While traveling as a child, I remember walking into hotels and attractions and seeing the wall-to-wall bank of brochures. I’d think, “How cool would it be to have a job where you got to write travel brochures for a living?”. As a kid, I thought it was one person’s job to write ALL of the brochures. I thought that person would get to travel to all of the attractions, write a brochure, and then move on to the next destination. That task of constantly traveling, writing, and producing brochures was my dream job!

Let’s fast forward about three decades. While I’m not writing travel brochures for a living, as Tidy Dad, I’m living out many of my childhood writing dreams. I’m also trying to live out my dream of exploring the world, and now that includes traveling with kids.

Traveling with kids

In 2016 we traveled with Mabel to Canada, visiting Ottowa, Montreal, and Quebec City.

In 2019 we traveled with Mabel and Matilda to Rome. Things have certainly changed since then, and our family has increased in numbers.

Emily and I traveled to London together in August 2022, and then in 2023 were inspired to take the entire family!

And we also added on stay in Paris!

Our next trip

In February of 2024, we’re off to Italy, Switzerland, and Germany! We’re flying direct from New York City to Milan, Italy to stay for a couple of days, then taking the train to Zürich, Switzerland, and will also make a day trip to Germany. There will be six of us in tow: Emily, Mabel, Matilda, Margaret, their Nana, and me.

This will be the second international trip we’ve taken as a family since Margaret was born in March 2020. The pandemic of 2020 and proceeding years have changed or cancelled travel plans for many people (including canceling our own trip to see the Queen during her Jubilee Celebrations in June of 2022).

Although there continue to be precautions in place, it is exciting to finally start to experience some renewed sense of travel normalcy.

Reducing the mental headache

Our upcoming trip is one of the most logistically complex that we’ve taken on with the girls. We’re literally traveling by bus, plane, train, and boat on this trip! I’m going to pull back the curtain and share the travel planning steps that we follow EACH time we plan a trip. The series of replicable steps has helped to reduce the mental and logistical headaches that can come with transporting our family to a new destination.

Traveling, especially traveling with kids, can feel overwhelming. But I believe that by tidying up the planning process, you can joyfully anticipate your trip and more fully enjoy your trip!

Here is my WHY, WHERE, HOW, WHERE, WHAT approach to travel planning!

WHY are we traveling?

Before planning a trip, we start with the WHY. As a family, we take several trips together during the year. Some trips are to visit family. Some trips are for adventure. Some trips are for rest or retreat. The question of WHY influences trip budget, length of stay, and logistical questions such as where we’re going, how we’re getting there, where we’ll stay, and what we’ll see and do in the destination.

Having a concrete WHY can help you answer the other logistical questions that follow.

After answering the WHY for the trip, I make a trip spreadsheet. I start by outlining the number of days and then chunk the day into time blocks. As travel related questions are answered, I update information in the spreadsheet accordingly.

Trip Spreadsheet

WHERE are we going?

Next it’s important to determine the WHERE. When brainstorming travel destinations with Emily, I often start with, “Here’s a place that I’ve always wanted to go to.” And she often replies, “There’s not a place in the world where you wouldn’t want to go!”

We try to travel multiple times a year with our girls. We balance visits to my family in Kentucky with weekend trips to our Woodland Cottage, trips within the United States, and trips abroad.

I teach in a New York City school and our kids go to school in New York City. Every February we have a week off from school and we’ve discovered it is a great time of year for international travel to Europe. Most European destinations are off-peak season in February, and direct flights from New York City are much cheaper. For our upcoming trip, our flights to Europe in February were only $50 more expensive per person than flights to Orlando Florida.

When flying, I love using Google Flights to plan trips. I love using the globe feature where you can search for flights in a range of destinations using filters including price, date, and number of connections. Several years ago, using the same method, we snagged flights to Italy for $270 round trip per person.

When we travel over our February break, we like to be flexible about the destination and use the Google flight feature to help us determine economical options for travel. We’ve also noticed that Tuesday – Thursday are typically the cheapest days to purchase airline tickets. For this upcoming trip, we purchased our tickets on Cyber Monday!

HOW are we getting there?

When traveling on weekend trips or to visit family we often drive. We like the flexibility of having a car and being able to easily get around in our destination. When flying, we try to book DIRECT flights. We’ve discovered that, particularly when traveling with kids, it’s worth the additional cost not to connect in another airport before arriving at your destination.

Most airlines have also changed pricing details on reservations and now charge extra for EVERYTHING including seat selection, carry-on bags, and number of checked bags. We’ve completely tidied up how we pack for trips and save money by packing light.

For a recent trip to the beach, we used Baby Quip to rent equipment that we’d need at our vacation destination. BabyQuip is a platform that connects families who are traveling with families in the area who have signed up to be local baby gear providers. Each provider has their own list of available items, and a location area where they’re able to deliver. Delivery charges vary based on the provider and the distance. We rented items like a beach wagon, beach tent, and water toys for the girls to play with while on vacation.

Whether we’re driving or flying we also have to determine whether we’ll pack a stroller, car seats, our baby wrap, or scooters. On a recent weekend trip to Washington DC we packed foldable scooters for the girls and they loved using them to get around The Mall. They are used to riding their scooters to and from school in New York City and loved being able to navigate around the monuments in our nation’s capital!

When flying, we always start by finalizing flights before we move on to the next step. I add the flight details to my trip spreadsheet and include the confirmation number.

Trip Spreadsheet

WHERE are we going to stay?

We’re returning to the WHERE question a second time. Selecting accommodations for the trip is the next major logistical question to answer. When we are traveling with our daughters, we love staying in Airbnbs. We’re Airbnb hosts and rent out our Woodland Cottage, and love the flexibility of being able to choose accommodations that have multiple bedrooms and a kitchen for cooking. It’s also nice to have extra space and a living room to spend time in once our girls go to bed, rather than sharing a hotel room.

Once accommodations are reserved, I add those details to my spreadsheet and link the confirmation details to the first hotel cell.

Trip Spreadsheet

WHAT are we going to do?

When traveling with kids, we try to plan one major activity for the morning, and one major activity in the afternoon. We build our itinerary around those activities and then fill the day with explorative play time and snack breaks. We look for parks and playgrounds for the girls to run off some energy!

The saying “early bird gets the worm” has proven true when traveling. When attractions first open, there are fewer crowds, which makes it easier to explore as a family and monitor the girls.

Once activities are reserved, I add those details to my spreadsheet. I also like to link email confirmations to the cell in the spreadsheet.

Trip Spreadsheet

Traveling with kids

We love traveling with our girls. For a short period of time, we take a break from our normal routines, we experience life in a new destination, and we make lifelong memories. We know that travel during this season of life looks different than traveling without kids, and we’re choosing to embrace it!

One of my favorite memories of our trip to Rome was sitting in a park overlooking the Colosseum. Emily and I were drinking coffee and eating pastries while watching Mabel and Matilda play. When traveling with the girls, we’re forced to slow down. We also spend a lot of time in parks and playgrounds. But there’s something so beautiful about sitting back and soaking in the sights and sounds of a foreign location, while watching your kids play. We’re experiencing new things together. Even if our girls don’t remember it all, we certainly will remember being there with them.

Muse vs. Amusement

We were recently talking to friends about their experience traveling to Paris with their young daughters. They said they enjoyed basking in the beauty of the city, the parks, and the lights. One of their favorite memories was sitting in front of the Cathedral of Notre Dame, opening their notebooks, and sketching it together as a family. They said the trip to them was a “muse”, which means a source of inspiration. They went on to say that “amusement” is the opposite of muse. Trips of amusement are designed to distract, entertain, and invite you to escape from reality.

In this season of life, we are looking forward to a trip filled with moments of muse. We’re excited to experience London and Paris with the girls. We hope to be richly filled with beautiful sights, enjoy scrumptious delights, and enjoy time together. We hope it will be a source of inspiration, a muse.

Trips are learning opportunities

By sharing how we plan for traveling with kids, I hope you’re inspired to think about how you can embark on travel adventures with your own family. Travel is such a beautiful gift, but can feel very overwhelming at times. There are so many logistics to consider, but answering the WHY, WHERE, HOW, WHERE, WHAT, can be a helpful place to start!

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