A week with family in Maui, Hawaii

When I turn sixty, I hope I can do exactly what my mom did to celebrate her birthday. She rented a big house in Hawaii for a week and invited her five children (plus spouses and children) to come spend the week with her. She then hired a local chef to cook dinner for the 15 of us every night, which meant we could relax each evening and enjoy dinner at the house without the pressure of booking restaurants and schlepping tired kids out of the house. While we tried to venture out for fun excursions during the day, we all gathered back at the house each evening for dinner and lots of relaxed family time. We sat around a big table, eating dinner, drinking wine, talking, and laughing. We put the kids to bed and stayed up late, playing games and laughing some more.

It’s funny what happens when you return to your family. No matter how much growing up I’ve done in the past 20 years, despite the fact that I have children and a family of my own… the minute you put me back at a table with my siblings and parents, I become a child again, slotting right back into my position in the family. It can’t be helped! I am the eldest of five. The responsible one. The bossy one even. 🙂 And somehow I find myself back in those childhood shoes again.  It really was so fun to have the opportunity to spend this special time with my family, back in one house together with no work to do and no where else we had to be.

The lucky thing about being the eldest of five is that when we get together with my family, I have four younger siblings to play with and love on my kids. There wasn’t a single swim in the pool for my kids without a crazy uncle to up the fun factor. From the minute we woke, Wilkie was whisked from my arms, fed breakfast and dressed before I could drink my coffee. I’d go to put suncream on my kids only to be told someone had already done it. At one point, I went to find the girls to tell them they needed to take a bath and get dressed for dinner only to find them under a thick layer of bubbles in the bath tub with my sister. My mom took at least one of my children with her every time she went out to run errands, and there was this constant supervision of children that made the whole week so relaxing. Not to mention, the kids got to play with their cousins, who they don’t get to see very often, and we got to cuddle a new baby boy who we hadn’t yet met. I can’t begin to explain how special it was for everyone to have this magical, condensed week together. Our kids were in tears when we left.

A highlight from this trip was taking my brothers out for a surf! They were such good sports about it, giving it a proper go for the sake of hanging out together. At one point, I was out in the surf with all three of my brothers, cheering them on to waves and laughing through it all. It was such a fun morning!

And of course celebrating my mom! The youngest sixty-year-old we know. She is a constant ball of energy and always up for fun. We always joke that she doesn’t have a slow gear; everything she does is done with gusto. I’m actually surprised we didn’t manage to get her out on a surf board! (I wouldn’t put it past her though — you should see her ski!) Again, I hope I’m like her when I’m sixty.

Because we stayed in a beautiful home and the week was mostly about spending time with my family, we didn’t explore the island as much as we would have otherwise. But what’s nice about Maui is that the island is small enough to explore pretty easily. We covered a fair bit of the island and never drove further than an hour away. Here are a few tips from some of our favourite adventures:


  • Hali’imaile General Store — We stopped here for lunch one day on our way back from Ho’okipa Beach and had a great Asian-inspired lunch with yummy cocktails too.
  • Paia Fish Market in Paia for freshly caught fish. Great for an easy lunch.
  • The Coconut Caboose roadside truck near Honalua on the northwest coast — serving the best coconut shave ice we ate in Hawaii, and coconut gelato too!
  • Whole Foods for groceries. We weren’t so impressed with the grocery stores near where we stayed, so it was worth the extra drive to Kahului (near the airport) to pick up food from Whole Foods.
  • The Fish Market in Lahaina — great for fish tacos!


  • Watch sea turtles emerge from the water and climb the beach at Ho’okipa Beach near Paia. We also found good waves here when it was pretty flat everywhere else.
  • Browse the cute shops in Paia. We found the cute ‘Aloha’ shirts for the girls in a cute shop in Paia (just around the corner from the Paia fish market). I think it was this boutique.  There were lots of other charming little shops in this town too.
  • Visit DT Flemmings Beach on the north west coast for good surfing waves (and no reef) and grab burgers from food stall adjacent. From here you can drive a bit further north to explore Honalua bay (and grab coconut shave ice from the Coconut Caboose).
  • Surf the breaks along the coast in Lahaina. They are all reef breaks, so you have to be very careful, but we took my brothers out in the surf and they managed okay. There are a couple surf rental shops in town and it’s all really easy to rent boards.
  • Visit the town of Lahaina.  We didn’t make it to the Lahaina Farmers Market, but apparently it’s quite good. There are lots of surfy and touristy little shops along the coast stretch in town.

12 thoughts on “A week with family in Maui, Hawaii

  1. I thought your mum was one of your sisters in the picture with the kids!
    We were just in Maui and loved Mama’s Fish House restaurant just outside Paia. Delicious seafood on the beach and it’s been there since the 70s so the decor is original island chic.

    • Oh I’m so glad you commented on this. We drove past and wondered if it was any good! What a beautiful spot. Hopefully readers will scroll down and read the comments for more suggestions, as we only just scraped the surface on our visit.
      And haha – my mom. She’ll love to read that. 🙂 xx

      • My other suggestion is spending a couple of nights in Hana rather than just driving there and back in a day. The eastern side of the island has completely different feel compared to the north and western, more remote, tropical and more local “Hawaiian”. Lots to see and do there as well – the famous black sand beach, waterfalls, tropical gardens and some delicious places to eat (lunch at Hana Farms was yum).

  2. You just made me miss Maui! It’s the only Hawaiian island I’ve been on, and we explored the whole thing and loved it. I want to go back with our kids sometime soon! We drove to Hana and then drove all the way around the eastern side of the island, which had a few scary moments but only adds to the fond memories now.

  3. What a fun trip!! I think that is amazing that your mom did that. We did a reunion with my in laws last year at the beach. There were 20 of us (10 kids, 10 adults) Kids ages 3-14. I have to admit it was very overwhelming and stressful. My husband is #3 of 5 kids. All the boys were nuts (We have three girls so not use to it. Just screaming and drama) and all the older kids were picking on my middle daughter. The oldest tossed her off of him when she was grabbing him while playing soccer (She was only 6 and had no idea how to play) That and one of the younger boy cousins thought it would funny to hold my oldest daughters arms while she was in the deep end. Non of the parents disciplined their children except for us. It seems like all of your children are so well behaved especially around younger kids. Bravo to you and your husband for raising children who are empathetic to others especially younger ones. Our trip turned me off so much I told my husband I would never do another family trip again.

  4. If I’m not mistaken, it is DT (not PT) Flemings Beach. Paia is lovely and we had amazing pizza at Flatbread Comoany right on the main street. Mamas Fish House was good but I don’t think it was worth the crazy expensive prices. Maybe better for a cocktail/appetizer but not for a large family unless you’re prepared for a very expensive meal.

  5. Hi Courtney! Do you have the link to the house you stayed in? We are planning a family trip to Hawaii this winter. The place you stayed looked beautiful! Thank you!

    • Hi Bridgette,
      How exciting you’re planning a family trip to Hawaii.
      Sorry, my mom booked the house, so I don’t have the details. And It was now a few years ago, so I don’t know if my mom will remember. But I can ask her and report back if I have more info for you! xx

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