How to Choose Where to Go on a Trip

People always ask me: How do you choose where to go for your next family trip with four daughters? And my answer is always the same: very, very carefully.

Because planning a vacation with four girls — ranging in age, opinion, snack preference, mucis n0n-tolerance, and mood swing velocity — is like trying to organize a symphony made entirely of cats. Loud, dramatic, beautiful cats. But still, cats. :)

We don’t just spin a globe and point. Oh no. Choosing where to go is an event in our house. A multi-phase, emotionally-charged, occasionally-tearful process that usually begins around the dinner table and ends with someone storming off because “nobody ever listens to me!”

Let me walk you through how it usually goes.

Phase 1: The Pitch Meeting

It always starts with me casually tossing out an idea, hoping to plant the seed.

“How about Greece this summer?”

Cue four wildly different reactions.

The Youngest (7): “Do they have unicorns there?”

The 10-Year-Old: “Do they have a pool with a slide?”

The 13-Year-Old: “I’m not going if there’s no Wi-Fi.”

The Oldest (16): “I don’t want to go anywhere basic. Everyone goes to Greece.”

Alright. Strike one.

So I try again. “What about Japan?”

Now they’re all interested, but for wildly different reasons. One wants to see cherry blossoms. One wants sushi. One wants anime. One wants to try every vending machine in the country (I hope it's not gonna happen..). I make a mental note: this has potential. But wait.

“Wait… how long is the flight?” someone asks.

“Fourteen hours.”

Gasps. Groans. “I’ll die.” “My skin will flake off.” “What if I have to pee the whole time?”

Strike two.

Phase 2: The Democratic Process (a.k.a. The Hunger Games)

At this point, I call a family meeting. Everyone comes armed with a list. I hand out notebooks. We make a rule: no interrupting. (It lasts about five seconds.) Nice try :)

Each girl presents her “top three (not less) dream destinations,” complete with reasons.

The youngest wants to go to Disneyland. Again. I can't do it anymore :)

My 10-year-old wants to go somewhere with wild animals but “not too wild” because she’s still afraid of goats. Yeah! No G-O-A-T-S! :)

The 13-year-old says Iceland because she saw a TikTok of a girl in a hot spring with snow falling around her.

The oldest wants to backpack through Europe and “live like a local.”

I try to explain that traveling with a family of five is not the same as starring in a romanticized travel vlog, but she waves me off.

I suggest we find some overlap. The room erupts.

Phase 3: The Reality Check

This is the point where I gently remind everyone that:

We are not made of money.

I cannot teleport.

We have to consider weather, travel time, costs, safety, visas, school schedules, and yes — even dad’s sanity.

I bring out my laptop and start showing photos.

Beaches? Mountains? Cities? Snow? Sun? Somewhere quiet? Somewhere wild?

Someone says, “Can we go somewhere with monkeys again?”

Another chimes in, “What about where we surfed?”

Then: “But I don’t want sand in my food every day.”

And finally: “Can we just stay home with air conditioning?”

I sigh. Deeply.

Phase 4: The Magical Middle Ground

Somehow, after weeks of scattered ideas, late-night Google searches, Pinterest boards, weather comparisons, and one spreadsheet that nobody but me looked at — a miracle happens.

We find it.

The destination that checks enough boxes. A place with beaches and hikes. With culture and coconuts. Enough Wi-Fi to make teenagers happy and enough lizards on the walls to make the little ones feel like they’re on a jungle adventure.

We chose Sri Lanka last year. The girls took turns reading facts about it aloud at dinner. They googled “what to pack,” learned a few words in Sinhala, and planned out their outfits like it was the Oscars.

We stayed in a beach hut. Ate roti and drank fresh papaya juice. We saw elephants. The youngest said it was “better than Disneyland.” My oldest journaled every day and called it “transformative.”

It wasn’t perfect — there was a spider the size of a small car in our bathroom one night. One daughter got sunburned. And I got scammed out of $20 by a very charming fruit vendor. But it was ours.

We chose it together.

So, Dad — How Do You Actually Choose a Destination?

Honestly? You don’t. Not entirely.

You guide. You listen. You nudge. You scroll late at night. You cross reference flight times and Google Maps and “Top 10 Things to Do with Kids in XYZ.”

And most of all, you remember: it’s not really about the destination.

It’s about the journey to getting there together — the planning, the dreaming, the arguing, the compromising. That’s where half the fun (and all the laughter) lives.

Because if I’ve learned anything from traveling with four daughters, it’s this: the best trips aren’t the ones where everything goes perfectly.

They’re the ones where everyone had a voice, even if it was loud and chaotic and borderline ridiculous. They’re the ones where the process was just as memorable as the passport stamps.

So next time you’re sitting at your dinner table wondering where to go next, just ask your kids.

Then clear your calendar for the next three weeks (minimum).

You're gonna need it.