The Planning Process

People often think we're a little crazy for traveling with four young kids — and honestly, sometimes we wonder if they're right. The part that looks like magic from the outside is usually just a process we trust: a handful of questions, asked in the same order, every time.

We do not start with hotels. We do not start with a Pinterest board. We start with the week we actually have, from a house in Tampa, with John, Beckett, Brooks, Baylor, and Britton in the picture. Everything else is a consequence of that.

How much time do we have?

A long weekend opens a completely different map than two weeks. Florida is a long-weekend state for us — Orlando, Marco Island, a stretch of Gulf light that does not require a boarding pass. A week-plus is when we start talking about going farther. The number of days is the first honest answer. If we skip it, we book a trip that looks good on paper and feels rushed in the room.

What time of year is it?

Season is weather, but it is also school, and it is also the version of a place we want. Niagara in the shoulder months is a different trip than Niagara in peak summer. Europe in fall is the lookbook we pack sweaters for. We hold the calendar next to the wish list and see which destinations are even in season for the days we have.

What is the budget?

Not a spreadsheet down to the snack. A shape. Flights, a hotel we will actually want to come back to at three in the afternoon, food, and one or two things that are the reason we went. With four kids, the budget is often the thing that kills a maybe. That is useful. It is better to know early than to fall in love with a villa we cannot stay in.

Can we fly direct?

We love a direct flight. If we are traveling with kids, avoiding a connection can make the difference between arriving as a family and arriving as a negotiation. From Tampa we are lucky — more of the map is nonstop than people expect. If the only way to a place is two connections and a four-hour layover, it usually waits.

Where do we really want to go?

Then, and only then, the wish list. Jennifer was born outside Toronto. That is not a destination we picked from a listicle. Make a short list of places you have been dreaming about — the ones with a reason. If there is somewhere you have been wanting to see, it moves to the top. The rest of the questions exist to protect that feeling, not to replace it.

Pick, then stop picking

Time, season, budget, flights, the wish list. The destination that checks the most boxes is the one. We do not keep a second “just in case” tab open. Indecision is how a trip becomes a spreadsheet with a boarding pass attached.

1. 01

   How much time do you have?

   Start with the number of days. A long weekend opens very different options than two weeks.

2. 02

   What time of year is it?

   Weather, school, and whether it is actually a good season for the places you are considering.

3. 03

   What is your budget?

   A shape for flights, hotels, food, and the one or two things that are the reason you went.

4. 04

   Can you fly direct?

   With kids, a connection is not a small thing. Direct is worth rearranging the map for.

5. 05

   Where do you really want to go?

   A short list of places with a reason. If you have been wanting to see it, it belongs at the top.

6. 06

   Pick your destination.

   The place that checks the most boxes. Then close the other tabs.

7. 07

   Now the fun begins.

   Where to stay, what to do, where to eat — and the little details that make it feel like a trip.

We try not to do too many activities in one day.

Now the fun begins

Destination picked. Now we plan where to stay, what to do, where to eat, and the little details that make it feel like a trip and not a transfer. This is the part people think of as planning. For us it is the second half. The first half was deciding what kind of trip this is allowed to be.

Stay somewhere the landmark can come to you if the day goes long — the Fallsview Marriott was that, in Niagara. Build in a meal that feels considered. Leave room for the mall, the ice cream, the thing that is just for joy. A trip with four kids does not get better because the itinerary is denser.

What this looked like in practice

Toronto was this process, written down as a few days: dinner at Amsterdam, the CN Tower, a winery in St. Catharines, Niagara Falls, Maid of the Mist, Avondale Dairy Bar. It could have been a checklist. We let it be a handful of true things instead. That is the edit.

The best memories aren't always the easiest ones to make. Sometimes they're the ones that take you a little farther from home.

They may not remember every toy or every afternoon at home. They will remember the spray on their faces, a new city, the feeling of discovering somewhere together. The planning is just how we get them there without losing ourselves on the way.