Planning Guide: 11 Steps to Planning a Family Trip (aka My Olympic Event)
I love daydreaming about our next adventure. Planning trips for my family isn’t always a breeze, but I genuinely enjoy it—it’s a little escape. The first two steps usually happen between Christmas and New Year’s, when the house is a mess, everyone’s in pajamas, and we’re setting our wild travel goals for the year.
1. Ask the family where they want to go. Everyone shouts five different destinations in five seconds. I nod with a great big smile and some strange looks and pretend I can make all dreams come true.
2. Narrow it down to 3-4 realistic options. This involves a complex algorithm of weather patterns, kid-friendliness, vibes, and my personal tolerance for whining. And honestly as long is there is a pool, no matter how big or small, I usually don’t get a lot of whining. They play well together when it’s just the two of them on vacation – at home it is a different story.
3. Decide Length of the trip and Pick dates that work for us, about 3-6 months out. Honestly, this is the most stressful part. With sports, dance, school, and life, syncing our schedules feels like trying to align the planets—and I’m not an astronaut, just a very determined mom with a calendar and a dream.
4. Enter destination and date combos into Google Flights, Hopper and Kayak.com. Aka, start my part-time job as a travel agent. I chase flight deals like it’s Black Friday. As a rule of thumb, I multiply the total round-trip flight time by $30 per hour—if the price is equal to or less than that, I know I’ve found a great deal.
5. Start researching hotels. This is my Super Bowl. I read TripAdvisor reviews like it’s bedtime fiction. Bonus: I keep checking even after I’ve booked. (Yes, I’m that person who might switch hotels two weeks before the trip because “something felt off.”)
6. Plan activities/tours 30–60 days out. I become a tour guide, historian, and meteorologist all in one. Is there a badge for this?
7. About three weeks out: the “Do you actually own what you need?” check. I pull out the packing list and realize 75% of it needs to be ordered online—again. I ask the kids if they have what they need for the trip: Sedona? Hiking boots. Exuma? Swimsuits that aren’t from three summers ago. Alaska? Everything waterproof and warm enough to survive a snowstorm. Their response? “I think so?” Translation: Mom’s about to hit ‘Add to Cart’ 47 times. This is my favorite gear when traveling HERE.
8. Two weeks out: I either book a rental car or set up airport pickup. My husband loves the idea of driving a rental car, so we usually go that route. It’s like his personal test drive every time we travel. We usually request a Grand Wagoneer so we can spread out and take naps because again we’ve been up since 3am. My husband lovingly refers to it as Zombie Day.
9. Pack light. The kids pack themselves and present their suitcase to us. Ha. They typically have to go back and sort some things out on their end but they continue to get better and better at this mammoth of a task.
10. Day before: Operation Departure. I clean the fridge, turn off the ice maker (learned that the hard way), and make everyone eat out so we don’t come home to a science experiment
11. Night before: early-ish bedtime. But we all know we’re waking up at 3 a.m. with that “Christmas morning” energy—because our flight is at sunrise and we’re headed to paradise!
I spend way too much time thinking of potential things that could go wrong, just to avoid the inevitable mini heart attacks I usually have on the first and last day of the trip—because somehow, that’s when everything goes sideways. So, If you think you’re the only one who freaks out, don’t worry—you’re definitely not alone!
When you arrive at the hotel, ask for an upgrade. When asked nicely, some of the front desk staff really enjoy giving an upgrade. Please do not expect an upgrade, but if given one please show lots of gratitude. Many hotels during slow periods will upgrade your room free of charge. The last time we went to Costa Rica, we were upgraded to an amazing family suite at Nayara Tented Camp and it was incredible, but it was during their slow season.
If you don’t yet have an American Airlines credit card for reward miles, please get one here. You’ll get 50,000 miles just to sign up and it will be the beginning of all your travel joys. As you spend, you’ll get more miles, and they add up quickly. Typically, every trip we go on, we use airline miles.
Some of our FAVORITE family destinations: Costa Rica, Key West, Alaska, Big Sur, Exuma, Grand Canyon and Paris. Check these out for destination ideas!
Please message me with any questions, I’d love to hear from you!
Safe travels. You’ll hear from me soon.
