Hawaii has a way of slowing everything down in the very best way, and Maui has quietly become one of our favorite places to be together. For the past few years, we’ve come every New Year’s, and it’s a tradition I really look forward to. There’s something so special about starting the year away, just the six of us, with no agenda beyond being together. It feels easy and familiar now — the same walks, the same stops, the same slow mornings — and those are the moments I find myself holding onto most.
This trip felt like a perfect balance of simple family time and a few really special experiences, and I wanted to share both what we loved doing and what I packed, because Maui style is all about being comfortable, unfussy, and ready for anything.
What We Did (and Loved)
One of the most memorable mornings was a whale watching sail with the Pacific Whale Foundation. The whole family went — baby included — and it was such a fun way to spend the morning together. The kids couldn’t stop talking about seeing whales breach so close to the boat, and it was one of those activities that truly worked for everyone. If you’re visiting Maui during whale season, it’s absolutely worth adding to your plans.
A trip to Maui wouldn’t be complete without dinner at Mama’s Fish House. It’s iconic for a reason — the setting is beautiful, the service is wonderful, and the fish is as fresh as it gets. It truly lives up to the hype, and it’s one of those meals that feels special from start to finish. I recommend booking well in advance and settling in for the full experience.
For something more casual, burgers on the west side at the Ritz-Carlton Kapalua were such a win. After a beach day, this was the perfect laid-back dinner with incredible views and very happy kids.
Paia quickly became a favorite stop. We loved wandering around town, grabbing shave ice, and taking in the laid-back, artsy feel. It’s such a fun change of pace and an easy place to spend an afternoon.
And for anyone who loves poke, the (secret) best poke is at Tamura’s Fine Wine & Liquors. It’s simple, unassuming, and so good — one of those spots you might drive right past if you didn’t know, but ends up being a repeat stop.
We also booked surfing lessons for the kids, which was such a highlight of the trip. Watching them learn, wipe out, laugh, and finally stand up on their boards was so fun — one of those moments that makes a family trip feel extra special.
What I Packed for Maui
When packing for Maui, I keep things simple and flexible. The goal is pieces that feel easy, work hard, and don’t require much thought once we arrive. I like everything to mix and match so getting dressed each day feels effortless.
Printed dress // crochette dress sold out (similar here)
Fashion
Lightweight dresses were the backbone of my suitcase — easy to throw on over a swimsuit during the day and just as perfect for dinner at night. I packed a mix of casual cotton styles and one or two slightly dressier options for evenings out. I also brought a few relaxed tops and easy bottoms for daytime exploring and travel days. Nothing too structured, nothing fussy — just comfortable pieces that still feel pulled together. A lightweight sweater or layer was essential for early mornings, whale watching, and breezy evenings by the water. Even in Hawaii, I always want something cozy on hand.
Accessories
I kept accessories minimal. A straw hat for sun protection, sunglasses, and a roomy tote that could handle beach days, snacks, and everything in between were all I really needed. For shoes, I packed a few pairs of everyday flat sandals and one slightly elevated pair for dinners. Maui is very much a flat-shoe place, and comfort wins every time.
Bikini // Skirt // Hat // White One-piece // Sandals // Pareo (similar here)
Swim
I brought a few swimsuits that I could rotate throughout the week, all comfortable enough for long beach days but still polished. An easy cover-up that doubled as a dress was key — perfect for quick lunches or walking around Paia without needing to change.
What I Packed for the Kids
For the kids, swimwear did most of the heavy lifting.
I packed multiple swimsuits and rash guards so everyone always had a dry option ready to go. Rash guards are a must for long days in the sun, especially with surfing lessons and ocean time built into our days. Beyond swim, I kept things simple with easy sets, lightweight layers for mornings, and one nicer outfit each for dinners out. Comfortable shoes, hats, and plenty of sunscreen rounded everything out. Less really is more here — especially when so much of the day is spent in or near the water.
