🎤 Episode Overview
After nearly 15 years of family travel — including a two-year backpacking gap year with kids — I’ve made a lot of mistakes, and I’ve watched a lot of other families make the same ones. In this episode of Family Travel Unpacked, I walk through the 9 biggest planning mistakes families make when booking trips with kids, and exactly how to avoid them.
From booking timelines and itinerary pacing to packing strategy and flight routing, this is the practical pre-trip framework I wish someone had handed me when we started traveling with kids.
🎧 Listen to This Episode
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🗺️ Episode Highlights & Timestamps
- 00:00 – Welcome
- 00:44 – Mistake #1: Waiting too long to book
- 02:46 – Mistake #2: Planning without everyone’s needs in mind
- 04:14 – Mistake #3: Overpacking your itinerary
- 06:40 – Mistake #4: Being too rigid with flights and routing
- 10:16 – Mistake #5: Under-researching weather and microclimates
- 12:04 – Mistake #6: Overpacking your suitcase
- 14:56 – Mistake #7: Not preparing for travel day
- 16:37 – Mistake #8: Not using points and miles strategically
- 18:31 – Mistake #9: Thinking short-term
- 19:55 – Wrap-Up
âś… The 9 Mistakes (and What To Do Instead)
Mistake #1: Waiting Too Long to Book
The best family accommodations — rooms that sleep four, vacation rentals, family suites — sell out early, especially for peak travel periods. If you’re planning a summer or spring break trip, start looking 9–12 months out. Flight prices and hotel award availability both tend to be better earlier too.
Mistake #2: Planning Without Everyone’s Needs in Mind
It sounds obvious, but it’s easy to fall into planning the trip YOU want to take and assuming the kids will go along with it. A trip that works for everyone means building in something for each family member — and being honest about what your kids actually enjoy versus what you hope they’ll enjoy.
Mistake #3: Overpacking Your Itinerary
This is probably the most common one. Families pack in too many destinations, too many activities, and too many “must-sees” — and end up exhausted and reactive instead of actually enjoying the trip. Fewer stops, more time in each place, and built-in buffer days make for a dramatically better experience.
Mistake #4: Being Too Rigid With Flights and Routing
Being flexible about routing can save significant money or open up better award availability. Consider flying into and out of different airports if it makes the itinerary work better. Think about connections vs. nonstops strategically rather than defaulting to the same airport every time. Sometimes a connecting itinerary is actually more enjoyable for kids than a long nonstop.
Mistake #5: Under-Researching Weather and Microclimates
Weather can make or break a trip, and it’s more variable than people expect. Many popular destinations have significant microclimates — the Big Island of Hawaii, for example, has completely different weather on each side. Do the research for the specific area and specific time of year you’re traveling, not just the country or island in general.
Mistake #6: Overpacking Your Suitcase
The weight, the fees, the logistics of hauling gear around — it all compounds on a family trip. A carry-on focused approach (with packing cubes) is achievable for most families and makes every transit day dramatically easier. If you’re going somewhere with laundry access, you can always pack lighter than you think.
Mistake #7: Not Preparing for Travel Day
Travel days with kids require snacks, entertainment, a charger, printed backup documents, and a plan for what happens when things go sideways. A little pre-trip prep — downloading shows, packing a dedicated travel day bag, knowing your airline’s policies — goes a long way.
Mistake #8: Not Using Points and Miles Strategically
Most families leave significant value on the table by not using points for family travel. Even a basic Chase Sapphire setup can save thousands of dollars on flights and hotels over a year or two of normal spending. The learning curve is smaller than people think, and the payoff is real.
Mistake #9: Thinking Short-Term
The families that travel most successfully with kids treat it as a long-term practice, not a one-off event. That means building a points strategy over time, getting kids comfortable with travel from an early age, and thinking about a travel calendar rather than a single trip. Small habits — using the right credit cards, booking early, keeping passport renewals current — compound into big results.