There’s no telling what kind of excitement might occur during one of our legendary Road to Hana tours. During my many years as a tour driver, I have seen all sorts of wonderful and amazing things happen… some funny, some not so funny; some expected, some not. Even the occasional heart-warming moments remind me why I enjoy doing what I do so much. It’s an adventure and, as such, all sorts of fantastic things can happen. There is one particular day that stands out in my mind. It started as one of those perfect Maui mornings: sunny, clear blue skies, perfect popcorn clouds and a light breeze that kisses your skin. The sunlight was shimmering on the waves with the deep blues of the Pacific stretching majestically out to the horizon. Perfect.

I had a particularly wonderful group this day. Everyone was in great spirits and several of the couples were celebrating special occasions… anniversaries, honeymoons, the like. It was turning out to be a great day (and we were just getting started). After enjoying a delicious breakfast at Ho’okipa Beach Park, we set off on our journey and it wasn’t long before the jaw-dropping views from the road began to take shape before our eyes: lush rainforests, breathtaking coastal landscapes, vivid flowering plants, tropical fruit trees, waterfalls, everything this world-renowned Maui road is so famous for. By the time we arrived at the black sand beach at Waianapanapa it was close to noon, so we decided to have lunch there. It was then, as we were getting ready to leave, that a young man in the group pulled me aside and asked if he could talk to me in private for a moment. He said today was a very special day because he was going to be proposing to his girlfriend and he wanted to do it at one of the stops along the way. I told him I thought that was a great idea and he asked if I could suggest a good place. All of a sudden the pressure was on because I knew I had to think of the perfect place. At first I thought about the black sand beach because we were right there and it’s a uniquely scenic spot. Then it came to me, the perfect place. A breathtaking waterfall called South Wailua Falls, which is one of the best waterfalls in the state of Hawaii and one that you can actually get to by road. They use it in a lot of the photo shoots and many times you’ll see pictures of it on one of the pages of the airlines’ in-flight magazines. A truly romantic spot, I couldn’t wait to get us there!

After driving a few more miles we hit one of the next stops. I pulled him aside and said, “Okay, when we get to the waterfall here’s what I suggest. The waterfall is located behind the bridge and there’s a small trail that leads to it. If you take your girlfriend and go down there, it’s a beautiful setting and there’s a perfect spot next to the falls to propose. The rest, my friend, is up to you. We’ll all be waiting. Good luck!” When we finally pulled up to South Wailua Falls, I parked the van and had him and his girlfriend get off first. He took her by the hand and they headed off for the waterfall. After they were out of earshot, I proceeded to tell the rest of the group what was happening. Everybody got very excited. From the bridge, we could see them walk down the path and eventually stop at the spot I had suggested. At this point I remember one of the ladies in our group saying “What if she says no?” The thought had actually never occurred to me. If she says no, I thought to myself, it could put a real damper on the rest of the tour, not to mention the poor guy’s heart!

A few moments later, he was down on one knee. By now, the bridge had filled up with other visitors who had taken notice of the event and, from our vantage point, we could see him pulling out the ring. For several seconds, it seemed as if we were all holding our breath, just waiting to see how she would respond. The minute she realized what was happening, she put her hand over her mouth and started crying. We couldn’t hear his words but, so far, it was looking like a success. Her joyfully sobbing face and emphatic nods that followed were the final giveaway. Then he placed the ring on her finger and we all burst into applause. It was a truly heart-warming moment and one that I will never forget.

After a long embrace, they made their way back from the waterfall and thanked me, saying how perfect a place it was for such a special moment in their lives. For the remainder of the trip that day, I remember the many smiling faces in my rear view mirror. It’s those smiles that inspire me to get up each morning and see what adventure the new day will bring.

-Jack The Legend