Traveling to Maui with a Toddler: Tips for a Smooth Family Trip

We took far too many photos during our six-night stay in Maui, so after a major cull we reduced them enough to make two posts (we admit we like to over-share). We wish we could have packed everyone in our suitcase, so posting the trip play-by-play is the next best thing. In this post we’ll cover:

  • where we stayed
  • where we ate
  • our “neighborhood”
  • how we saved money

In the next post we’ll cover:

  • the activities and adventures we tackled with a toddler in tow
  • a home-related souvenir we bought to remember the trip
  • the vacation “tradition” we continued in Hawaii

We also wrote about flying with a toddler and helping her adjust to the time change over on Young House Life.

First up: where we stayed. We rented a small condo at Aina Nalu in Lahaina, on Maui’s west coast, through HomeAway. Booking directly with the owner via that site saved us a significant amount compared with booking the same resort through the front desk or a travel agent. At the time, comparable rooms were being listed at $185/night, which would have cost roughly $126 more over six nights. In our area of Richmond, basic hotel rooms run $150–$175 a night, so a two-bedroom condo with two bathrooms, a full kitchen and a washer and dryer for less than that felt like a great deal. The beach, shops and restaurants were all within walking distance, and we loved both the neighborhood and the condo itself.

The owners had made the place very kid-friendly. They provided a pack ’n play, a stroller, plenty of beach toys, and safety features like outlet covers and cabinet latches. We’d researched child-friendly areas of Hawaii and focused on properties with high ratings on HomeAway before booking, and the condo definitely delivered. The Aina Nalu lobby felt welcoming and well-kept.

We booked a two-bedroom unit because our toddler, Clara, sleeps much better with her own room. The main bedroom had an en-suite shower, and the extra space was absolutely worth it for our family. Some units at the resort functioned more like hotel rooms with housekeeping and keycards, while ours was a true residence with a regular key and no daily housekeeping. We liked the privacy of feeling like it was our own condo. There were plenty of towels and an in-unit washer and dryer, so we did laundry mid-trip—a lifesaver for sand- and ice-cream-covered clothes.

The grounds were laid out with pathways to the various buildings, the lobby and two pools. Some days the pools were busy, but other days we had them almost to ourselves. There were plenty of loungers for sunning and shaded cabanas that felt like king-sized beds by the pool—perfect for relaxing with the toddler.

We each picked a souvenir item to remember the trip: John got a blue Hawaii tee, I bought a soft Maui shirt, and Clara picked pink Crocs she calls her “rocks.” They were great for sand and surf—waterproof and easy to rinse off.

About Lahaina: it’s a charming walkable area with plenty of shops and restaurants. Several beaches were within easy walking distance from our resort. One favorite was “Baby Beach,” where coral reefs shield the shore and create calm, shallow water that’s great for little kids. There were some rocky patches of coral, but staying near the shoreline made it easy for Clara to splash safely. Sometimes she sat waist-deep and splashed, poured buckets of water on her head after counting to three, or simply played at the water’s edge for hours.

We made sure to apply plenty of SPF, turned off our phones most of the time, checked email for only about 30 minutes a day, and I didn’t wear makeup the whole week. It was blissfully low-maintenance. When we got hot we hopped in the water and kept an eye out for whales beyond the reef. While we didn’t spot any from every beach, we had several memorable whale sightings at other spots during the trip.

One fun memory: Clara was fascinated by a small kayak that drifted by with a little girl and a dog onboard. She gazed silently until it passed, then announced at full volume, “little girl and doggy on on on on on a boat! Hi doggy! Hi little girl! Hi boat! Hi man!” Her excitement is contagious.

Now for food. Maui surprised us with a lot of delicious options. Highlights included a fried rice breakfast from Lahaina Coolers, Loco Moco at Aloha Mixed Plate (John got a hamburger on his; I had an egg on mine), burgers from Cool Cat Cafe (praised as one of the best on the island), and a giant slice of Hula Pie from Kimo’s. Lahaina Coolers and Kimo’s provided crayons for kids, which earned parental gratitude. Lahaina Pizza Company served great pie with an upstairs balcony offering ocean and harbor views, and a cold angel hair pasta salad I adored.

We had a funny hibachi experience when a big flame terrified Clara, who shouted “fire is hot!” and cried. We stepped outside while John grabbed the meal to-go, and ended up eating in a cabana by the pool. It was chaotic and hilarious and definitely one of those stories we’ll laugh about for years.

Clara loved local treats like shave ice, ice cream, bagels and french fries. When she wasn’t into a dish we kept crackers, fruit and veggies on hand. At one restaurant she proudly identified letters on an “Aloha” sign; a waitress gave her a flower, which Clara joyfully sniffed in her own hilarious way.

We also witnessed some spectacular whale activity from Aloha Mixed Plate—huge splashes that drew everyone’s attention, followed by the thrill of watching a whale breach. Even after multiple sightings, each one felt as exciting as the first.

Other eateries we enjoyed (without photos) included:

  • Take Home Maui (a deli known for fresh pineapple)
  • Sunrise Cafe (a reasonably priced local breakfast spot)
  • Bradda Hutts (an amazing BBQ stand near Hana)
  • Auntie Sandy’s (fresh-baked banana bread at Ke’anae Peninsula)
  • Sure Thing Burgers (a local organic burger stand in Lahaina)
  • Moose McGillycuddy’s (a sports-bar-style place we found just okay)
  • Cheeseburger in Paradise (a waterfront spot with great views)
  • Fred’s (a Mexican restaurant in Kihei we enjoyed)

One must-try: Ululani’s shave ice. There’s a difference between coarse “generic” shave ice and the fine, snow-like Hawaiian shave ice. Ululani’s is delightfully fine and flavorful; they’ll even add more syrup if yours starts tasting icy halfway through, which is a nice touch.

How we saved money on the trip:

  • We’d been saving since our last big trip five years earlier, which helped with the overall budget.
  • We watched airfare pricing and found that booking midweek (Tuesday night/Wednesday morning) often offered better fares, and booking about 2.5–3 months ahead worked for us.
  • We used HomeAway to find a two-bedroom condo with a washer and full kitchen for about $164/night, which also included baby gear so we didn’t have to bring it.
  • We carried on luggage to avoid checked-bag fees and the risk of lost bags, knowing we could do laundry in our unit.
  • We bought basic groceries and cooked some meals in the condo to offset restaurant costs, and we often split entrees to reduce the bill.
  • We booked some excursions online or through discounted vendors—our resort had an Expedia booth offering deals on activities like whale watching, and some attractions offered online booking discounts.

That’s Part 1 of our Hawaiian trip recap. The next post will share the excursions and activities we enjoyed, the house-related souvenir we purchased, and the vacation tradition we carried on. Meanwhile, feel free to share favorite restaurants, activities, or tips for Maui or Hawaii in general—we’d love this to be a helpful resource for future travelers.