Hawaii Family Vacation: Tips, Highlights, and Itinerary Guide

How about some Hawaii Two-O — yes, a cheesy nod to Hawaii Five-O — which can only mean one thing: here’s the second (and final) post about our trip to Maui. If you missed the first post last Thursday, check it out to read about where we stayed, where we ate, our “neighborhood,” how we saved money, and what traveling with a toddler was like, including tips that worked (and which didn’t).

In this post we cover the activities and adventures we tackled while in Maui with a toddler, the home-related purchase we made to remember the trip, and the vacation tradition we continued while in Hawaii.

Our main activity was the beach — this trip was all about relaxing. We weren’t chasing nonstop adventure like snorkeling, zip lines, or dinner cruises; after three weeks of nonstop projects for a book and little sleep, we wanted to decompress. Still, we fit in a few memorable outings.

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One full day was dedicated to driving the Road to Hana. We stocked the car with snacks, diapers, fuel and a guide CD, then set out for the scenic, winding route that everyone says you should do while in Maui.

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The scenery didn’t disappoint. The highway itself was nerve-wracking at times — nearly constant curves that got tighter and narrower the further we went — but the views made it worthwhile.

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We didn’t hike to every waterfall like some Hana travelers do — hiking with a toddler can be tricky — but we enjoyed many sights from the road, including waterfalls visible from the highway.

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We spent extra time exploring the Ke’anae Peninsula, where dramatic waves crashed against cliffs and a roadside stand sold incredible banana bread that we still dream about.

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Another highlight was Waianapanapa State Park. The park offered spectacular coastal features: a distant sea arch, a blow hole where water shot up through a rock, a cave, and a remarkable black sand beach.

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The black sand, formed from lava rock, was unlike anything we’d seen. Clara loved it, and so did we.

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Two small setbacks happened after this: the skies turned overcast, and our camera battery died. Still, we drove on to Hana, had lunch at a roadside BBQ, and completed the full loop around the island. Some people stay overnight in Hana, but since Clara was napping and we wanted to see more, we kept going. The full loop took about eight hours with several stops, and Clara did surprisingly well — frequent stops helped her stretch and stay happy.

We made it back in time to recharge and caught a beautiful sunset in Lahaina.

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Another big adventure was whale watching. After spotting whales from shore, we decided to take a boat trip so Clara could see them up close. We were a little nervous about being at sea with a two-year-old, but the trip went well overall.

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Clara behaved admirably, with only a brief meltdown. We even tried the “Young Naturalist” program on board, though Clara’s idea of participating involved making new kid friends in a very hands-on way. Once she settled down, she enjoyed finding a vantage point and watching for whales.

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We did see whales — mostly blows and occasional tail sightings. Regulations require boats to keep a respectful distance, so there weren’t dramatic breaches, but seeing them in their natural environment was impressive.

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Beyond car and boat excursions, we explored a lot on foot. Our condo was close to Lahaina’s highlights, so long morning walks (often interrupted by breakfast stops) led us to planned places and a few delightful surprises.

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One unexpected find was the Lahaina Jodo Mission: a serene Japanese temple and a large Buddha statue tucked around a corner, offering a peaceful cultural detour.

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We also discovered animals in unlikely places. The Hyatt Regency at Kaanapali had flamingos, black swans, and even African penguins roaming the grounds, plus a gorgeous pool and oceanfront paths perfect for strolls.

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The Maui Ocean Center was another highlight and a great, toddler-friendly alternative to snorkeling. The aquarium’s underwater tunnel surrounded us with fish, sharks, and stingrays — a dry, comfortable way to see ocean life up close. It was the perfect final stop on the island before our late-night flight.

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As part of our vacation tradition, we write postcards to ourselves to document each day. We usually keep them instead of mailing them, filling the backs with highlights like where we ate, what we saw, and goofy anecdotes — like Clara’s hiccup at a hibachi dinner.

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We also brought home a small souvenir: a historic map of Maui printed on canvas. It’s a visually appealing piece that complements the U.S. map we use for marking trips and gives our home a bit more Maui memory.

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Overall, the trip left us relaxed and grateful for family time with Clara — and missing our dog Burger the whole time. We came home with sun-soaked memories, a stack of postcards, and a new canvas map to remind us of Maui. Do you have any trips coming up? We’d love to hear about them.