A Hawaiian Family Holiday


With lots of family and friends out of state, most of our big, summer family trips are driving to see them. Once in a while we take off for a few days at the beach, or maybe Sunriver. This year, however, my husband and I decided to splurge. After taxes, we ran the numbers, cashed in all our airline miles, and used every “companion fare” the airline would allow to book a trip of a lifetime for our family of five.


We polled friends and family on social media, researched cruises, thought briefly about the Florida Keys or the US Virgin Islands, but finally settled on Hawaii. This launched a new search of the best Island to visit. Kids wanted to do Disney’s Aulani, the husband wanted to go the Big Island, but eventually we decided on Maui. Thanks to Costco Travel (and a hefty tax return!) we booked six days at a family-friendly, cultural resort.


My husband had never been to this particular hotel and the kids and I have never been to any of the Hawaiian Islands before so we were all pretty excited but had few expectations about this first, big family trip. How would the kids (5, 7, and 9) do on a six-hour flight across the Pacific? Would they want to see the sites, experience the culture, and be willing to try new adventures? Could we make sleeping arrangements in two, adjacent hotel rooms work? And the biggest, most important question; would I have enough sunblock for Hawaii?!

As per the norm, I started packing a week in advance. Yes, I am that OCD. I loaded backpacks with Love Rocks, library books, Playaways, and Target dollar-bin coloring books. I completely overthought the amount of clothes we would need (Hawaii called for rain some days, so like every good Portlander, I packed rain jackets and sweatshirts!) And I scoffed at my husband’s insistence that we would need six bottles of oxybenzone-free Alba spray sunblock for the kids.

hawaiiBut finally the morning came to leave PDX. We long-term parked our car, hopped on the shuttle, and lugged our crap all over the terminal like a professionally traveling family. The nonstop flight from PDX to Kahului was long, but the kids did great, and we arrived in humid Maui (when has 80 ever felt so hot?!). We got our rental car (yay, Costco Travel!) and drove across the island and up the coast to Ka’anapali, stopping at a roadside stand for fresh Hawaiian produce, and admiring the THOUSANDS of surfers and boogie boarders lining the beaches from Ma’alaea to Lahaina.

We checked in to the lovely and hospitable Ka’anapali Beach Hotel, settled into our room, and hit the pool (after first applying sunblock at 5:30 p.m. because that’s apparently what mainlanders are supposed to do!) The next six days flew by as we visited fun restaurants, rented boogie boards, took a dolphin-watching boat tour, visited a pineapple plantation, got a nanny so the hubs and I could attend a luau, shopped in Lahaina, took Hawaiian cultural classes offered by the resort, and hit the resort pool every afternoon and evening.

hawaiiHaving never visited the islands before, it was very important to me to learn and experience as much culture as we could. I wanted our children to understand the rich, native heritage and respect it. It was one of the main reasons we chose the hotel we did. Dubbed “Hawaii’s most Hawaiian hotel,” the cultural classes they offered did not disappoint! We learned to speak the Hawaiian language, made both ti leaf (hilo) and string flower (kui) leis, threw fishing nets, played the conch shell and nose flute, and even learned the hukilau hula! By the end of our stay, the staff knew us and our children very well, and when it was time to say goodbye, it really felt like we were bidding “a hui hou” (until we meet again) to friends and family.

And now we are already planning our next visit to Hawaii…hopefully as soon as November!