Maui, 2025
When I travel, I typically look up at the world around me, taking in the environment and observing the local culture. But now, as a mom, traveling has essentially turned into me constantly glancing down at the stroller next to me. Is she still napping? Is this too warm? Should we go back to the hotel room?
All jokes aside, even though we now have a lot more bags to lug around and flights to over-prepare for, I’m determined to continue traveling. My trips and travel stories will now look a little different, as I adjust itineraries to fit into nap schedules and give up doing anything after 6pm. My goal is no longer to see new places for myself, but to show my daughter this big beautiful world and hopefully instill in her a love for exploration. I thought Hawaii would be a good place to start.
We invited Simon’s family to tag along, booked flights, and committed to five days in Maui right at the tail end of my maternity leave.
The highlights
Staying at a resort! I never grew up with the means to ever consider a resort, so being greeted by leis like rich families do in movies was exciting. We stayed at the Westin, and I loved walking into a huge indoor-outdoor lobby everyday greeted by the sound of a thunderous waterfall and animals (flamingos, parrots, koi fish)
Watching sunrise from our hotel room balcony and the Kaanapali beach walk. And being able to do so in shorts.
Living at the beach!
Doing a workout class under the palm trees. Can’t all my fitness classes take place here?
Going down a water slide (albeit into the kids’ pool)
Catching the Black Rock Torch Lighting cliff diving ceremony
Fresh acai bowls and poke everyday
ʻĪao Valley State Monument hike
Snorkeling for the first time and seeing a giant turtle (!)
70° weather, day and night. This was the best part about being in Hawaii, especially as the Bay Area experienced almost freezing temps this week. Even baby girl seemed to enjoy not having to bundle up in a fleece onesie 24/7 like she does at home.
Seeing countless other families take their babies and toddlers on vacation, and thriving
The not-so-glamorous moments
Realizing that we can’t afford Maui. Food, tours, water activities, rentals, and even groceries are insanely priced for whatever “luxury” they claim to be
Realizing that the more affordable activities involve driving 2+ hours (volcano summit, Road to Hana), which just wasn’t possible for us this time around
Having to plan our days (and change plans on short notice) around nap times. On our last day, we cut our beach and snorkel time short because baby wouldn’t stop crying from being overtired
Getting sunburnt
Having to end our days early because 5pm meant bedtime in PST
Traveling with baby
Even though people will tell you it’s hard, it’s worth it. Here’s what worked for us.
Borrowing a Doona to use as a carseat-stroller combo. It was so easy to strap into an Uber or rental car, and convert into a stroller when needed. Makes transitioning between walking and driving mid-nap more convenient.
Stuffing the stroller bag with diapers so you don’t have to pack them into your luggage. We tried Coterie diapers for this trip, but weren’t impressed.
Breastfeeding to not only nurse on-the-go, but also to comfort a fussy baby during flights.
Free extra bags we brought onto the plane: breastpump bag, insulated cooler bag with milk, and stroller bag (gate checked). TSA made me take the pump out individually to go through the scanner, and quickly inspected the milk. You also have to carry the baby through the scanner, so an extra hand would be helpful with stroller collapsing/pushing.
Traveling with grandparents or other family so you can get adjoining hotel rooms. This way, when baby goes down at 6pm, you can hop over to the other room and not have to sit in silence and darkness. We brought our baby monitor to keep an eye on her from the other room.
Bring your own bedsheet for the hotel crib
It’s a privilege being able to travel, especially to a place where you can go about your day in shorts and a swimsuit. Island life just hits like a warm hug—the air is soft, the colors are bright, and your whole mood shifts into easy, sun-soaked happiness. Despite the added difficulty, it was a joy getting to travel with three generations of family. I won’t forget the nights we spent cooped up in the same room, eating a takeout dinner, chatting away, and laughing at everything.
Living the island life in the dead of winter, with baby in tow.