The 4 family travel rules I swear by

Juan Ruiz

August 4, 2026

Table of Contents

I stopped booking the earliest flight possible
I break up long travel days whenever I can
I always contact hotels or Airbnb hosts before arrival
I never board a flight without the essentials my kids need

Reading Time: 4 min

I’ve always been a planner — probably an over-planner. After traveling to more than 25 countries with my twin daughters before they turned 10 and now traveling with a preschooler, I’ve realized the trips that go smoothly usually come down to having better systems in place before we even leave home.

These are the four family travel rules that genuinely make trips feel easier for me, my wife, and our kids.

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I stopped booking the earliest flight possible

As a morning person, I used to love booking the first flight out. Arriving early and maximizing the destination on day one was always appealing. Plus, those early departures are sometimes the cheapest flights and tend to leave on time more often, before airport congestion, weather delays, and rolling cancellations start piling up later in the day.

But I stopped booking them because my family isn’t just me. Rushing everyone through a chaotic 4 a.m. airport morning usually meant we arrived exhausted before the trip even really started.

Now, I intentionally build in slower travel mornings whenever possible. I’d rather arrive a little later and have everyone in a better mood than force an ultra-early departure just to save a few dollars or points. Sometimes paying a little more for a mid-morning flight is worth it if it means the trip starts off calmer for everyone. I’m trading away some of that early-departure reliability, and I know it — but a delayed flight with rested kids still beats an on-time one with melting-down kids.

I break up long travel days whenever I can

Long-haul travel days with kids feel much longer than they sound on paper. We’ve been to Hawaii from South Florida several times, and at first I thought it made sense to just power through and get there in one shot. But two long flights, airport connections, delays, meals, and time zone changes can easily turn into a 15-hour travel day — and by the end of it, everyone is completely drained.

Now, we almost always break it up with an overnight stop on the West Coast in places like Phoenix or Los Angeles. Everyone gets a real night of sleep to reset, and the second travel day feels like a short hop instead of a marathon. It isn’t only a comfort play, either; splitting a long flight across two days can come out cheaper than the nonstop.

We’re doing something similar this summer on our trip to Mallorca. Instead of rushing to immediately connect after landing in Barcelona, we’re spending a few nights there first before heading to the island. It makes the whole trip feel calmer and less rushed.

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I always contact hotels or Airbnb hosts before arrival

A quick email or message before arrival can make family trips go much more smoothly.

At hotels, I usually confirm items like a travel crib, a rollaway bed, or an early check-in request ahead of time. For Airbnbs, I’ll often coordinate arrival details and ask about basics we may need if we’re landing late.

One thing that helps a lot is asking Airbnb hosts ahead of time if the rental already has basics like bottled water, toilet paper, or snacks. That way, after a long travel day, we can go straight to the listing and relax instead of making an immediate grocery store stop with tired kids.

I never board a flight without the essentials my kids need

The older my twins got, the easier flying became. But when they were younger, I learned pretty quickly that comfort and familiarity mattered a lot on long travel days.

We always packed favorite snacks, familiar pillows or blankets, and little comforts from home that made flights feel less overwhelming. Basically, a scaled-down version of the gear we rely on for long-haul flights.

Now with a preschooler, preparation looks a little different because she’s not really an airplane napper. We always bring fresh fruit, snacks she actually likes, downloaded iPad shows, coloring books, crayons, and a few favorite small toys in her backpack.

None of this is groundbreaking parenting advice, but having familiar activities and comfort items ready before boarding makes flights significantly less stressful for everyone, including me.

Nothing here requires a complicated system. It mostly comes down to deciding in advance where I’m willing to trade a little money, time, or efficiency for a calmer trip — and with kids along, that trade is almost always worth making.

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