Trip Talk No. 4: Maggie's Family Trip to Hawaii
And the free "souvenir" idea we'll all want to steal
Have you read The Life Council by Laura Tremaine? Tremaine names and defines ten categories of friends that bring value to our lives: the daily duty friend, the old friend, the business bestie, the fellow obsessive, the battle buddy, the yes friend, the mentor, the password protector, the new friend, and the soul sister.
Maggie falls into the “fellow obsessive” category. We’re both big readers and never tire of hearing each other’s hits and misses. Not gonna lie, I was thrilled when Maggie agreed with my hot takes on Real Americans and Long Island. Check out her Substack for her reading round-ups and get ready to add some titles to your TBR list!
About Maggie: Maggie lives in Frederick, MD with her husband and five children. She used to teach high school math (and studied math in college specifically to avoid writing papers and reading books she didn’t like). Now, she spends all of her free time reading, listening to the podcast What Should I Read Next?, and abusing the curbside pickup service at the library.
LOGISTICS:
Where did you go? Hawaii (Oahu, specifically!)
Was this your first time traveling to this destination? Second time! I went six months earlier with just my two-year-old to help my sister with her baby. My sister lobbied for me to come back with the rest of my family, so we took her up on it.
How long were you there? Ten days + two travel days
Who did you go with? My husband and our four children (our fifth wasn’t born yet). The older two were 7 and 9, and my little two both had birthdays on the trip! They turned 3 and 5.
How do you approach travel spending? Obviously, the biggest expense of this trip was the airfare. We weren’t planning to go until we had this flukey windfall of thousands of dollars worth of Southwest vouchers that needed to be used within a year. We booked our flights home on a Wednesday when flights were cheapest. We splurged on two big experiences (ziplining and an ATV tour) and did lots of free activities like hiking, beach trips, and borrowing my sister’s kayak. I stocked up at Costco our first day there, packed lunches for our outings, and made breakfast and dinner at home most days.
PRE-TRIP
Were you the one solely responsible for planning the trip, or did you share the responsibility with someone? My sister sent me a list of her favorite things to do around the island, and I checked out one or two travel books from the library. I created a detailed itinerary and collected feedback from her and my husband, who was just grateful that I did the planning.
How long did it take to plan? We booked the flights in May and traveled in August. I spent a couple of hours each week in June and July reading guidebooks, strategizing with my sister over the phone, and using Google Maps to figure out which outings could be done back-to-back.
What was the most enjoyable part about planning, and what was the least enjoyable part? Researching and organizing our daily plans (including the two birthdays!) satisfied my need for control, but I couldn’t ignore my suspicion that the plans would fall apart once my actual human children were involved. And, unsurprisingly, the itinerary fell apart immediately because my kids needed downtime! But I was still so glad I had taken the time to create it. Because I had studied the locations and hours of all the things we wanted to do and decided ahead of time which activities would be first to get cut, it was easy to rearrange plans as we went.
What were you most nervous about? Travel delays, jet-lagged children, driving my gracious hosts crazy, and not fitting in enough experiences.
ON THE TRIP
How did you get to your destination? Do you have travel anxiety? Did everything go smoothly? I prepared for my nightmare scenario (flight delay causing us to miss our connection and any chance to get food during the layover and I’m stuck with hungry/grouchy children for 20 hours) by bringing two days worth of food in our carry-on bags.
The planes were on time, but we nearly missed our 6:30 am flight out of Baltimore because we found an unconscious (drunk?) young man in the street in front of our house at 3 am and used up our huge cushion of time knocking on neighbors’ doors and then waiting for an ambulance to arrive. (He was fine).
My children’s misbehavior was limited to my five-year-old shredding and then stomping on the free lei from the rental car company while we waited to pick up our car at the Honolulu airport. Not bad.
Tell us about a challenging moment. How did you handle it? On the way home from a rare two-activity outing (read: extra exhausting), our minivan, which was full to capacity with my household of six people plus my sister and her 11-month-old, sat in stopped traffic on the interstate watching smoke billowing from a vehicle that caught fire while we wondered how long we would be stuck there. Thankfully, the kids all had new souvenirs in their laps to amuse them, and the holdup only lasted an hour. I was calm (calm-ish—no need to reach out to my husband to fact check here) but inwardly panicking about our nearly empty water bottles and low gas tanks.
What surprised you? About eight days into the trip, when I was feeling a little exhausted and ready to go home, my sister mentioned that her husband said he was sad we were leaving in a few days. This from a man who moved into his guest room with his wife and toddler for ten days to free up the master bedroom and nursery for a little circus of houseguests!
Another surprise: the best beach spots are on military bases! My completely useless advice for anyone visiting Hawaii: stay with family members who have military IDs so you can access quiet, beautiful beaches.
What media did you consume on your trip? Sometimes we watched the YouTube channel of a professional surfer with my brother-in-law after the kids were in bed. I spent at least half an hour each evening using the free Clips app to create a little video highlight reel from the day’s adventures. The kids loved watching them when they woke up the next day and we rewatched these videos constantly for months.
Do you have any activities/restaurants you’d recommend?
The CLIMB Works zipline experience was expensive, but worth it!
The pillbox hike in Lanikai is short (less than half an hour to the top, with an enthusiastic 5yo leading the way), and the view is incredible
Sunrise on Lanikai beach on the first day of the trip works great for travelers coming from East Coast time!
Waimea Falls “hike” is actually a stroller-friendly, flat-ish walk and worth the long drive and small admission fee!
Shave ice in Hawaii is not to be missed! We tried it at several shops, and it’s delicious!
POST-TRIP
What was the hardest thing for you to face when you got home? Jetlag! For four days after we returned home, all of my children were still awake until after 1 am and struggling to wake up before 11. They returned to Eastern Standard Time just in time for school to start a couple of days later!
Do you have any routines in place for easing back into “normal life”? I didn’t then, but I sure do now! After coming home to an empty fridge and a dozen pieces of luggage to unpack after 20 hours of traveling with four children, I now schedule a grocery pickup for the day we return from any trip!
Did you bring home any souvenirs? The kids each selected one item from the Navy Exchange: t-shirt, piggy bank, bracelet, decorative sea turtle dish. But I treasure those videos I made in the Clips app each night of the trip! Two years later, we still rewatch them at least once a month.
And finally… what did you learn about yourself through this trip? When I was a child, my genius parents included a lot of downtime for us when we traveled. If we were going somewhere for 6 days, then day 3 and day 5 would be designated rest days during which we’d see a movie or play cards. I planned enough activities for us to be constantly on the go in Hawaii, but we often did one outing for a few hours in the morning and then laid around in the afternoon. It felt like a waste of time to rest at all—did I fly 5,000 miles so we could watch tv and nap??—but it also felt necessary. We could have squeezed in more activities, but only at the cost of everyone’s enjoyment of the trip.
1. I love that Maggie packed two days worth of food into carry-on bags to avoid having hangry children. 2. I can’t believe the bit about the unconscious man in front of their house and almost missing their flight!!! 3. Her brother-in-law being sad about her family leaving—so sweet! 4. Why have I not been making videos of our vacations? Genius! This line made me LOL—“I couldn’t ignore my suspicion that the plans would fall apart once my actual human children were involved.”
Some discussion questions: Have you been to Hawaii? What are your go-to airport/airplane snacks? Are you for or against including downtime in your itinerary?
And in the spirit of my bookish friendship with Maggie, what was the last great book you read on vacation?
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I love this series SO much!! The Oahu photos are stunning. Love the travel spreadsheet! Another +1 for down time on vacations. I feel toddler schedules work well on vacations: breakfast, big outing outside, lunch, nap and chill, something calm and outside, sleeeeeep.
Again, such a fun series! I loved this! I've been to Hawaii once (The Big Island) for our honeymoon. I would love to go again, but the thought of taking all the kids feels a bit overwhelming (and super expensive). We, sadly, do not have any military connections there, so that's a bummer. ;) I always feel the same about resting when traveling, like it's a waste of vacation time, but in reality, it's a necessity. At the beginning of this month, my parents kept our kids for a full week (7 days/7 nights), so that was basically my summer vacation. And I read "It's a Love Story" -- so good!