I had so many DM’s about our trip to Maui! (and for those who messaged me after our Feb 2024 trip, sorry this is so late!) After I answered questions and sent back to back to back suggestions over DMs, I received a “thank you” and also a “why don’t you write a blog post”. So here we are! Before I dive in, here’s some quick demo facts about us to consider while reading:
So far, we’ve taken 3 trips to Wailea Maui with our kids. We try to go at least once a year. Stay tuned for updates for 2025 and beyond!
2023 – August – 2 year old (27 months), and I was 6 months pregnant
2024 – Feb/March traveling with a 3.5+/almost 4 year old, and a 15 month old
and later in 2024 – Nov/Dec traveling with a 4.5 year old and 2 year old (24 months)
– flight time: 6 hours one way – PDX to OGG
– our preferred time of year to visit Maui: February/March
– our preferred town on the island to stay: Wailea
Here is what I’ll highlight in this post: where we stay, affordable family-friendly activities and where we love to eat. Plus, other kid stuff: what we rent while we’re there (crib, car seats, beach wagon, etc) and how we like to travel with young kids. Get ready! Some might be the unpopular opinion!
Why we stay in Wailea? It is in proximity to our favorite places, beaches, and the condo village we like to stay in! Wailea Ekahi Village- Our favorite beach condos! We’ve found and booked all 3 stays on Vrbo or Airbnb, but I recently (post-trip) now see a new website dedicated to the property. We’ve stayed in 3 different units on the property. I do not recommend booking a condo that’s managed by Maui Beach Vacations because they do bare minimum expectations and it’s been a hit or miss on cleanliness and functional a/c. If you can, try to book with personally owned+managed vacation rentals. However! We did enjoy the location and style of our most recently booked condo (Nov 2024 trip) which is managed by Maui Beach Vacations. Because of the location and style of the condo, it outweighed the lack of hospitality from Maui Beach Vacations and we would book again. The condos are located beach front, on our favorite beach- calm, quiet and kid-friendly, (between Keawakapu Wailea-Ekahi Public Beach Access and Mōkapu Beach). The condo village is also right next door to the public path that goes along the beach front to Andez, Four Seasons, etc – a beautiful morning or sunset walk!
Did we rent a car? Yes! we rent a car so we can go outside of Wailea. Depending on where you’re staying, what you’d like to go do and see, you may or may not need a car rental. We like to make it to the Upcountry Farmers Market, and prior to the fires, Lahaina. We absolutely rent car seats when traveling so we don’t have another thing to lug through the airport.
Things to know about OGG – take the trolly to the car rental. Yes it says it’s a short walk. it’s not a short walk if you have kids and luggage and kids. Take the trolly!
“Gear” we packed:
Compact + lightweight stroller: Colugo
Slumberpod with fan
Toddler Swim Vests
Pack n play mattress (to pack, we use the vacuum compression storage bags linked below)
What we rent: Beach wagon, rent a pack and play or travel crib. Who we rent from: We’ve used her 3x! https://www.babyfurniturerentals.com
We rented a highchair previously but only used a few times. Our kids do great sitting at the table in general, and if needed, a few pillows did the trick. We also sit outside to eat quite a bit. We have brought/packed our booster seat and prefer that over the rental highchair.
Fun reef safe sunscreen for kids: these color sunscreen sticks are from Australia so you know it’s the good stuff! Make sure you get make-up wipes to get off/careful to get it on clothes, couches, towels, etc! 🙂
Our condo has: Tommy Bahama beach chairs, umbrella, cooler, and sand toys.
Packing tip: Amazon Basics Vacuum Compression Space Saver Zipper Storage Bags with Hand Pump
What we purchased ahead of the trip but did not use/need: Flyaway inflatable toddler bed for the flight.
By the airport: Top Chef’s favorite, Sheldon Simeon’s restaurant is right there! Tin Roof – so delicious! Don’t miss out on it. Take something to go!
Costco (540 Haleakala Hwy, Kahului, HI 96732) is also right around the airport and is great if you’re staying awhile and plan to eat in or need staples for the kiddos. If your condo, or lodging amenities do not have beach umbrellas or sand toys, there is also nicely priced items available at Costco.
Around Wailea:
Ululanis is the best shaved ice. https://www.ululanishawaiianshaveice.com
To luau or not to luau? I don’t recommend splurging on a luau if you have small kids. If you want to see a show, there’s a great one (for free!) at the The Shops at Wailea shopping mall. The events page has other great activities that they offer too! DO THIS: We love to book a reservation at Tommy Bahamas for happy hour and then head to the Polynesian show – you can check the website for dates and times. Tommy Bahamas has an awesome HH menu, and they give (and mail for you!) postcards to send Grandma and Grandpa (or anyone!).
There’s some yummy ice cream shops right by the performance stage, and an affogato seems to always help with the the jet lag combo with the kids waking up early as they adjust too. Another hula show option: South Maui Gardens! We love us a food truck pod – and South Maui Gardens has over 10 delicious choices to choose from, it’s super kid friendly with space for them to run around and roam, + it’s a garden so expect a beautiful atmosphere! They also have live music occasionally so check their website. We also enjoyed their hula show* (see reel below!) which is more reasonably priced than a resort luau. There is no alcohol for sale on the property but you can bring your own. (*sponsored event)
Farmers Markets – our absolute favorite is to plan a Saturday morning and head to Upcountry! http://www.upcountryfarmersmarket.com. The Arepa stand there are incredible! Pick up some fresh fruit and veg! Another great farmers market options is the Wailea Village Farmers Market (Tuesdays currently) https://waileavillage.co
Another fun (and free) activity for the kids: Koi Fish – The Fairmont Kea Lani (Wailea) has Koi Fish feedings for the kids at 9am every morning. https://www.fairmont-kea-lani.com
Favorite places to eat around Wailea:
Cinnamon Rolls Place – the best GF cinnamon rolls!
Maui Ono Donuts – the BEST GF donuts!! GF or not, they’re really the best. (make sure to place the order the day before).
Da Kitchen – featured previously on Dinners, Drive-ins, Dives! Great for a quick option, mixed plates, kid-friendly, consistently delicious.
Humuhumunukunukuāpuaʻa – inside the Grand Wailea! It’s great for a date night, or if your kids can handle a sit-down meal. The atmosphere sends all those Hawaiian vibes, with a beautiful view. They also have a cool new aquarium bar!
Monkey Pod – make a reservation! kids can eat butter cheese noodles for free. And great HH for mom and dad. The deviled eggs are the most delicious deviled eggs! There’s usually live music so check the calendar!
*Prior to the fires* Possibly has changed since* Headed to Lahaina? Plan a morning and go to the Hyatt to watch the penguins feeding + the interactive koi fish feeding, and then head to Mala Ocean Tavern for lunch! The restaurant sadly burnt down in the Lahania fires and was one of the first restaurants in the area to reopen. It’s one of our favorites! The ube pancakes are delicious. and it’s a kid-friendly spot too. It’s right on the water, and we’ve seen sea turtles swimming in the wild while we’ve enjoyed lunch!
The not so important, but important opinions: The best sandals for comfort and sand are Tevas! I have these babies in the “maple sugar”. On my first trip to Maui, I made the mistake of taking sandals that were not made with the ocean and sand in mind (they were cute, comfortable, fashion forward, sold at Nordstrom), but they completely fell apart during the trip. My favorite swimwear and cover-ups are from VETCHY. Favorite kid shoes for a trip like this: Natives. Full sleeve and pant swimsuits for the kids from Columbia Sportswear – Amazon Link.
I hope a trip to Maui is in your future! Sunshine + the aloha spirit is always a good idea 🙂 If you have any questions or need more info, shoot me a DM or email! ALOHA!