Just realized I had a ton of help from Reddit on our itinerary and other things, so here's our trip from a couple months back -- it was awesome. Passing it along in case it helps folks -- especially those w small kids.
We mixed plenty of easy beach and resort time with a little adventure, some incredible scenery, and great food. It was enough to keep everyone excited without exhausting ourselves.
We spent most of our time in Kaʻanapali, with two nights in Hāna so we could enjoy the Road to Hāna without rushing. Here's what we did, along with some recommendations.
Wednesday, May 20 — Travel Day
Flew from Minneapolis to Maui via Seattle, arriving around 10 p.m.
Picked up a Turo rental car.
Stayed overnight at Maui Seaside Hotel near the airport.
Since we were getting in so late, we figured we'd stay near the airport, wake up early, and get a full first day in Kaʻanapali rather than paying for an expensive resort night we'd barely use.
Thursday, May 21 — Kaʻanapali and Resort Day
Headed to The Westin Nanea Ocean Villas in the morning.
Enjoyed the pool and, thankfully, were able to check into our room early.
Spent the rest of the day exploring the resort and beach.
The Westin Nanea was absolutely spectacular. We travel a lot, and I've never stayed at a better resort. We booked through a heavily discounted Marriott Vacation Clubs promotional offer, which required attending a vacation-ownership presentation. If you're willing to sit through the sales pitch, these offers are definitely worth exploring. We got a 6-day, 5-night stay for around $2250.
Friday, May 22 — Snorkeling and Luau
Morning pool time and breakfast.
Stopped at a scenic overlook near Kapalua.
Visited Kapalua Bay for snorkeling and beach time. Our kids were over-tired so didnt stay long.
The relatively sheltered bay, easy entry, colorful fish, and possibility of sea turtles make it a great spot for families with younger kids. Parking fills up quickly.
Flexible lunch and afternoon back at the resort.
Evening: Attended the Wailele Luau at the Westin Maui.
The luau was definitely pricey, especially for a family of five, but we thought it was worth it. It's several hours of dinner and entertainment, so it really feels like a full evening's activity rather than just a meal. The girls loved it, although a couple even managed to fall asleep toward the end :)
Saturday, May 23 — Relaxing in Kaʻanapali
Easy morning enjoying the resort.
Noon vacation-ownership presentation, part of the accommodations. This ... is not for us. It was not very high-pressure.
More beach and relaxation time.
Dinner at Duke's Beach House.
Duke's was particularly enjoyable. Eating outdoors right by the beach was a wonderful experience, and a great setting for a family dinner.
We also loved the outdoor live music around Nanea during our stay. Those relaxed evenings were a big part of what made the resort so special...
Sunday, May 24 — Tropical Plantation and Exploring
10 a.m. tour of Maui Tropical Plantation.
Drove to Waiheʻe Ridge Trail.
We only did a portion of the trail with the kids, but even the drive out and getting to explore part of it was cool. Beautiful scenery, but some Hana-like roads 😅
Relaxed afternoon.
Parents' date night at Māla Ocean Tavern in Lahaina.
Monday, May 25 — Surfing, Sea Turtles, and Pāʻia
8 a.m. surf lesson with Got'Um Surfing.
Drove toward the North Shore and Pāʻia.
Stopped at Hoʻokipa Beach Lookout to see sea turtles resting on the beach.
Explored Pāʻia, a laid-back town with walkable shops and boutiques.
Returned to our resort for the evening.
The surfing lesson was one of the highlights of the entire trip. Several people recommended Got'Um Surfing, and we're glad we listened. Highly recommend them.
Hoʻokipa was also a fantastic stop for seeing sea turtles.
Tuesday, May 26 — Road to Hāna, Day One
We decided to spend two nights in Hāna rather than doing the entire drive in one day. This gave us much more time to explore and was a great decision with three young kids.
7 a.m. — Leave Kaʻanapali
Packed swimsuits, towels, snacks, drinks, and plenty of supplies for the kids.
8:30 a.m. — Twin Falls
Easy trails and waterfalls.
Swimming opportunities when conditions allow.
Fresh fruit stand was great, esp the sugarcane juice.
Good place for a bathroom break.
10:30 a.m. — Keʻanae Peninsula
Beautiful coastal scenery.
Banana bread at Aunty Sandy's.
Had approximately 30 minutes to explore, which was more than enough.
Lunch — The Bamboo Hale at Hāna Farms
We stopped for pizza at Hāna Farms' Bamboo Hale, an open-air restaurant surrounded by tropical greenery. The pizza was awesome, and the atmosphere made it an especially memorable lunch stop.
3 p.m. — Waiʻānapanapa State Park
Reserved our entry ahead of time.
Explored the famous black sand beach, lava formations, and incredible coastal scenery.
The caves were particularly cool to explore --
Spent approximately 90 minutes there.
Late afternoon: Checked into our Airbnb in Hāna and relaxed.
Wednesday, May 27 — Pīpīwai Trail, Hāna Beaches, and Food Trucks
Early morning: Headed to the Kīpahulu District of Haleakalā National Park.
Our main adventure was the Pīpīwai Trail to Waimoku Falls.
Approximately 4 miles round-trip.
Gorgeous bamboo forests, bridges, waterfalls, and rainforest scenery.
Also explored the area overlooking the Pools of ʻOheʻo ... however it was mostly closed due to rain.
This hike was an enormous highlight of our trip. Somehow, we managed to complete it with a 10-, 7-, and 4-year-old. It wasn't exactly effortless, but it was an extraordinary experience and one of the most memorable things we did in Maui.
Afternoon:
Relaxed at Hamoa Beach, a beautiful, dramatic beach near Hāna.
Enjoyed a slower-paced afternoon after the hike.
Food trucks in Hāna:
The food truck area in Hāna was another definite highlight. It's a fun, casual place to grab something to eat, with several different food options. The Thai food was particularly great. Definitely worth a stop while you're in town.
Thursday, May 28 — Return to Kaʻanapali
Drove back from Hāna.
Checked into The Westin Maui Resort & Spa.
Spent our final full day in Kaʻanapali.
After our experience at Nanea, this resort was a disappointment. It was considerably more expensive, and I simply wasn't a fan. The service was not good (our kids got yelled at for touching an adults-only pool? Very odd) and the pool needed cleaning 🤢Having stayed at both, I'd enthusiastically recommend Nanea over the Westin Maui Resort & Spa.
Friday, May 29 — Heading Home
Packed up and returned our rental car.
Afternoon flight from Maui to Seattle.
Overnight near the Seattle airport before completing our journey home.
Hopefully this helps other families putting together a Maui trip, particularly those traveling with younger children. Happy to answer questions about our experience!
I also threw together a little video of our trip if anyone wants to see some of the places we visited:
Our Maui Family Vacation — YouTube