Aloha, Maui: A Homeschool Graduation Trip to Remember
Days 1 and 2: Touchdown, Snorkels, and Surf Prep
We flew into Maui and landed midday! Thankfully, we live on the West Coast, and so we were able to secure a direct flight, which was roughly 6 hours. We flew Hawaiian Airlines for the first time, and that was a fun start. REALLY RECOMMEND 🌺
First order of business: a quick Costco run right next to the airport to stock up on essentials. We were staying in the Kaanapali area of Maui, which was about an hour away. We also found an amazing food truck court (these are very popular and common in Maui) and had amazing burritos and steak salad.
Settling into Kanapali Royal felt like a dream—quiet grounds, condo‑style space (so much less hustle than a big resort!), and easy beach access right beside Whaler’s Village.
As soon as we unpacked groceries and dropped our bags, we wasted no time diving into the ocean, and within 5 minutes of snorkeling, we were seeing turtles and beautiful, bright fish. We watched the sunset before calling it a night. A long 17-hour day, but so worth it.
The next morning, we spent time at a good surfing beach (for beginners) for my oldest daughter. Since this was her (and my) graduation trip, her request was to surf. So we found a good beach and set up there for the day before we went out to dinner at Hula Grill for Father’s Day. And hubs had his first tomahawk steak. We did some sunset family beach pics since this was our only “dress up” day. We had done a traditional luau when we visited Kauai, so that wasn’t a priority this time. We got to bed somewhat early because the Road to Hana was a 5 am wake-up.
Days 3 and 4: Road to Hana & Cliff Jumps
The next day, we spent 15 hours (including driving there and back) on the road to Hana. We purchased the Gypsy guide and downloaded it ahead of time to listen to the history of the area and the road, as well as have sights pointed out for us. This is important because you will lose cell service. Luckily, we had our friends with us who had gone before, and so they were our guides and took us to a few lesser-known spots. Swimming in all the waterfalls, all the hikes; It was stunning, and tiring, but so so worth it. It’s the only jungle area on Maui, so it’s a must-do! But just be prepared, have extra chargers for phones, drive slowly, and start early. And know you’re going to encounter one car, one way at a time, on bridges.
After the loooong and tiring Hana day, we spent the next day at Black Rock Beach, where you can cliff jump into the ocean. The tide was pretty strong, so we wore snorkel gear out and then had Teva sandals to climb the rocks and take the 35-foot jump. The water at the beach was beautifully turquoise, and it was a sunny, clear day. Afternoon winds kicked up sand, so we retreated to our condo kitchen for a home‑cooked dinner, then capped the night with another beginner surf session and—of course—family‑style shaved ice. Sooo yum!
Days 5 and 6: Pearl Harbor Pilgrimage & Final Snorkels
Next up was a bucket list item for my son and husband: Pearl Harbor. We did what is called an island hop and went from one to the next on a quick 25-minute flight for the day, and flew from Maui to Oahu. The day prior, we secured tickets for the ferry out to the USS ARIZONA and toured the USS MISSOURI. If you want to come, plan ahead to make sure you get the tickets you need, and when they release. We were glad we did this while we were in Maui because taking a trip specifically to Oahu isn’t something we want to do or plan to do in the future.
It was incredible to stand where Japan surrendered and WWII ended. As well as visiting the USS Arizona memorial to honor and remember those who died that December day.
The next day, we were still recovering from the day trip to Oahu. (I’d recommend tacking it on the end or beginning of a trip to Maui, not a there-and-back) So we set out for a restful day in the sun. We walked a beautiful nature trail, and then we were off to Kanapali Bay, which has the best snorkeling on Maui. We swam with turtles, swam the entire bay, and the color and the fish were incredible here. That night, we came back for a sunset walk on the trail for more amazing views! Both of these are must-dos!
Then it was our last full day on the island. And since this trip was for my oldest's graduation gift, she wanted to get some surfing in again. We went to the best surfing beach (for beginners and intermediate surfers). She spent a few hours surfing, and then we grabbed some macadamia-nut lattes from Vintage Island Coffee. After that, we joined our friends who were staying nearby for some pool time and our last round of delicious shaved ice. We came back to our condo, bbq’d some turkey burgers, and cleaned up the condo.
As we loaded the car for our homebound flight, I reflected on how richly God blessed our family on this graduation trip—moments of awe at creation, laughter in unexpected places, and the sweet privilege of watching our girl chase waves (and dreams!). Homeschooling has taken us on so many adventures, but this one—our first cap & gown celebration—will forever hold island sunsets and turtle‑kissed memories in my heart. Mahalo, Maui!
