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About Maui Legend Tours

Specializing in Exclusive Private Tours on Maui, including Road to Hana Tours, Beach Tours, Upcountry and West Maui Tours.

About Maui Legend Tours

Maui’s highest rated tour driver, Jack “the Legend”

At Maui Legend Tours, we believe any tour is only as good as its guide. That’s where our company founder, Jack “the Legend“, comes in. Maui’s most-requested, highest-rated tour guide, Jack has been telling the stories and legends of Hawaii for over 30 years. With his infectious sense of humor, spell-binding story telling gifts, and extensive knowledge of Hawaiian history, it’s no wonder Jack is a perennial favorite in the industry. He has hosted well over a thousand sightseeing tours to Hana alone.  As one of our visitors recently observed,

“Jack’s gift lies in his ability to weave it all together like an exciting adventure story, transporting the listener back to another place and time.”

In a review posted on Trip Advisor, another passenger writes:

 “I highly recommend taking a Maui Legend Tour with Jack. I was lucky to have beautiful weather on my experience for the Road to Hana. What made it even better was Jack’s colorful and thoughtful tapestry that wove all of the Hawaiian history together for me in one day through the spoken word. I appreciated how he waited for certain landmarks to stop and start the story again… it was sort of like having commercial breaks from a fascinating movie.”

Google “Jack the Legend Maui”

But don’t just take it from us! Google “Jack the Legend Maui” for yourself and check out his glowing 5-star ratings and reviews.




Maui Legend Tours founder Jack “the Legend”

Maui Legend Tours founder and visionary, Jack “the Legend”, first started making a name for himself while driving for one of the busiest tour companies on Maui. During this time, he began developing his craft and unique style of story-telling, fast becoming the company’s most-requested tour guide. Soon a nickname began to surface, although no one, including Jack himself, knows the original author of this fitting title. It didn’t take long before word of Jack “the Legend” began to spread online, in forums and by word of mouth. Five-star reviews began to pepper the tour and travel sites with statements like 

“If you’re ever on Maui, do yourself a treat and get on one of Jack “the Legend’s” Hana tours. The guy really knows how to weave a yarn and turn an already amazing trip into pure magic!”

To this day, when Jack tells of how the idea for Maui Legend Tours was born, he gives credit to one passenger, a fellow veteran tour guide who happened to be part of a group that requested Jack as their guide. A mule-back guide who lead groups up and down the Grand Canyon, he immediately recognized Jack’s talent and the two quickly hit it off. During lunch they swapped stories, talked shop and realized they both shared a belief: the most important element of any tour is its guide. Later, at the end of the day as the group was departing the bus, he said “You know Jack, you’re way too good at what you do to be working for someone else. Have you ever thought about starting your own tour company?” Jack never forgot that. 

Less than a year later, Maui Legend Tours was born.   

“Today I’m going to be telling you the incredible story about the Hawaiian Islands and it’s people… This is the history and legends of Hawaii… Today, YOU are going to be part of the legend.”


A Message from Jack “the Legend”

I love history. Especially as it relates to diverse cultures. With its fascinating stories and age-old legends, Hawaiian history is no exception. During my time as a tour driver on Maui, these themes have become a centerpiece of the way I conduct my tours and somehow, over the years, I seem to have developed a knack for telling them. How Hawaii ended up becoming our 50th state is arguably one of the most fascinating stories in history and one that I still love to tell after all these years.

While hosting my Road to Hana, Maui Island and Private tours, one of the things I like to do is talk about specific historical events while we are at the places they actually occurred. It seems to add excitement, creating another dimension to the experience. An good example of this is the Hawaiian word “heiau”, which means ancient religious temple. This is something we actually get to stop and see along our Hana sightseeing tour and, when we do, I tell a true story that occurred in and around this particular heiau many, many years ago.

Some of the biggest waves on earth pound areas of shoreline we pass while on your Road to Hana adventure. With these waves come some interesting facts and events that occur even to this day. Additionally, you will discover one of the incredible mysteries of the great volcano, Haleakala, and how lava flowed out from its crater to form what is now the Keanae Peninsula. The ancient Hawaiians also did some amazing things to transform this location into the incredible landscape you see today.

You can learn all this and more, by reserving your seat on one of our legendary Maui tours today.


-Jack “the Legend”

More about Jack here