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So you may have heard of this tour driver on Maui they call Jack the Legend. I stumbled across him on my iPad one evening while perusing the internet for things to do on Maui (I had heard great things about the road to Hana but had also read about how stressful it can be for those who attempt to drive it themselves). And there he was all over the place… Travelocity, Trip Advisor, Yelp, Facebook… you name it. Jack The Legend. Jack The Legend. Jack The Legend.

With reviews like:

“Jack is the man! Best tour my wife and I have ever taken, bar none.”  

“Definitely take Jack’s tour! The stories are worth it, Hana is amazing, and it’s a totally fun and relaxing trip.

“If you can request a driver for the Road to Hana tour, get him!
He bewitched us with his stories, legends and history of Hawaii for nearly 10 hours.
Such a fun time…”

In celebration of our tenth anniversary, my wife and I were getting ready for our much-anticipated ten day trip to Maui. So I immediately booked a tour and put in a request for Jack The Legend. Fast forward to the morning of our tour. As we were stepping aboard the tour bus, I asked the driver “Are you the infamous Jack The Legend?” A big grin spread across his face. “That’s what I hear”, he chuckled. Little did we know what a truly special day we would have with Jack as our guide.

For the next nine or so hours, it was as if we were all catapulted back in time, to a strange and exotic world where a completely isolated culture existed for centuries on this chain of jewels that Captain Cook called The Sandwich Islands. We were literally right there in the middle of it, watching it all unfold before our eyes: breathtaking views everywhere you look, far beyond anything my wife and I have ever experienced. To this day, it was without a doubt the single best tour either one of us have been on. And Jack the Legend was the maestro.

The road to Hana is a 50-mile snake of a road that winds through some of the lushest, most jaw-droppingly beautiful rain forests, coastal lines and waterfalls you can imagine. It is punctuated by bright floral reds, purples, yellow-golds and nearly every other shade of color imaginable. Because of the nature of the road itself, and the fact that most of it is one lane wide, it takes a few hours to get to Hana. What Jack adds to this experience cannot be over-stated. Not only does he have a thorough knowledge of Hawaii, its history, culture, and people, he also manages to somehow weave it all seamlessly together, both past and present.

For those of you who have never taken this tour, you really, really should. And with Jack at the helm, it is sure to be an experience you will not soon forget. 

-Bill Stapleton