Private Road to Hana Tour

5 (6)
Paia, US
5 (6)
Paia, US
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Experience the breathtaking beauty of Maui's eastern coastline on the Private Road to Hana Tour. Immerse yourself in a world of flourishing rainforests, cascading waterfalls, and mesmerizing seascapes. Your journey will take you to the tranquil town of Hana, considered one of Hawaii's last unspoiled gems. Take in panoramic views, relax on a black sand beach, and savor a delicious lunch at a local eatery. Throughout the day, Jack "the Legend," Maui's most sought-after tour driver, will regale you with captivating stories, legends, and the colorful history of the Hawaiian Islands. With rave reviews and a 5-star rating, Jack's infectious enthusiasm will keep you entertained and inspired. Embark on this once-in-a-lifetime adventure and discover the magic of Hana and beyond. Aloha!

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 9 hours
  • Suitable for 1-1 Participants
  • Private Tour
  • Guided Experience
  • Immersed in enchanting landscape
  • Flourishing rainforests and flowing waterfalls
  • Swimming at a black sand beach
  • Delicious local eateries for lunch
  • Hear colorful history, stories, and legends
  • Private transportation
  • Soda/pop
  • Bottled water
  • Snacks
  • Lunch
  • Air-conditioned vehicle
  • Breakfast
  • Coffee and/or tea
  • Pickup & drop-off service to all the hotel resorts and most condos, except the travaasa hana hotel
  • Beach towels
  • Sun block

Popular Hotels Closeby

More about this experience


Experience the beauty and tranquility of Maui's eastern coastline on the Private Road to Hana Tour. Escape to the unspoiled Hawaiian frontier of Hana, where you'll be surrounded by lush rainforests, picturesque waterfalls, serene pools, and breathtaking seascapes. Your knowledgeable tour driver, Jack "the Legend," will regale you with fascinating stories, legends, and the vibrant history of the Hawaiian Islands and its people. With a quick Google search of "jack the legend maui," you'll discover his well-deserved 5-star reviews from delighted customers. Immerse yourself in the hidden gems of Hana and create memories that will last a lifetime.

What to Expect?

Prepare for a full day of adventure and discovery as you embark on the Private Road to Hana Tour. This captivating journey spans approximately 9 hours, ensuring you have ample time to explore the wonders along the Hana Highway. Witness the captivating beauty of Maui's natural landscapes, from the world-famous Road to Hana loop to the remote stretches of Route 36. Immerse yourself in the scenic vistas, where nature's wonders unfold at every turn. Delight in the opportunity to swim at a black sand beach and savor a delectable lunch at one of Hana's charming local eateries. Throughout the tour, Jack "the Legend" will enlighten you with his extensive knowledge, providing captivating insights into the rich cultural heritage of the Hawaiian Islands.

Who is this for?

The Private Road to Hana Tour is designed for adventurers and nature enthusiasts seeking an escape to untouched beauty. Whether you're an avid photographer, a curious traveler, or simply someone eager to immerse yourself in Maui's raw splendor, this tour is perfect for you. Considered one of the last unspoiled frontiers, Hana provides a serene and awe-inspiring experience for all who visit. No matter your age or travel preferences, this tour guarantees an unforgettable journey through Maui's breathtaking landscape.

Why Book This?

Uncover the allure of Maui's eastern coastline on the Private Road to Hana Tour. Unlike traditional tours, this experience is led by the legendary Jack, whose storytelling and passion for the Hawaiian Islands will ignite your curiosity. With his wealth of knowledge and infectious enthusiasm, Jack ensures an engaging and educational adventure. Immerse yourself in the untamed beauty of Hana, from its vibrant rainforests to majestic waterfalls and secret pools. Revel in the chance to swim at a black sand beach—a truly unique experience. Additionally, the decadent lunch at local eateries allows you to savor the flavors of authentic Hawaiian cuisine. Book this tour and allow Jack to unlock the secrets of Hana, creating memories that will truly last a lifetime.

Good to Know

During the Private Road to Hana Tour, be prepared for a full day of exploration, lasting approximately 9 hours. Keep in mind that the tour covers the entire Road to Hana loop, showcasing the scenic wonders along the way. From the start of the journey, you'll be captivated by the mesmerizing landscapes that unfold before your eyes. To ensure your utmost comfort, bring along comfortable walking shoes, swimwear, and a towel for your beach visit. Stay hydrated and pack sun protection, as the Hawaiian sun can be intense. Indulge in the delicious local cuisine during the lunch stop, savoring the unique flavors that exemplify the island's culinary delights. Immerse yourself in the beauty of Hana and let Jack be your guide to this hidden treasure.


Customers rave about the Private Road to Hana Tour, particularly thanks to the charismatic and knowledgeable tour driver, Jack "the Legend." Travelers have hailed Jack's storytelling skills, which paint a vivid picture of the Hawaiian Islands' history and culture. His engaging manner and ability to make the tour come alive have garnered him countless 5-star reviews. Guests have expressed their gratitude for the opportunity to witness the breathtaking landscapes of Hana, including the stunning Road to Hana loop and the renowned black sand beach. Many praise the well-planned itinerary, allowing ample time to explore Hana's treasures. With Jack as your guide, expect an extraordinary adventure that surpasses all expectations.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Your Itinerary

Hana Highway - Road to Hana

This tour does the entire Road to Hana loop.



5 (6)


We were a family of four with two (adult) children. We had heard about the treachorous road and while we weren't scared of the driving we just didn't know what we wanted to see since there is sooo much to do. We were glad to someone so greatly informoed. Jack did not disappoint. Not only did he listen to our wishes we had put in place but he made sure every member had the best experience possible. Firstly, his car is comfortable for four people and could easily fit more. He had enought water, sodas and a wide array of snacks to last during the whole trip. His headset makes it easy to understand him. Communication was very easy and he listened to our wishes and made a perfect day. He is very knowledgable about the legends of Hawai'i and the Road itself. There were spots where we were completely alone! He also was able to secure an entry permit for the black beach which was on our wishlist. He informed us well about what to bring We also went to a great restaurant for lunch too and as everything is included in the price we were not stressed one bit. All in all I really reccommned Jack the Legend Maui and I think it was wort every penny.

Grace L

Amazing private tour experience!! Jack was knowledgeable (provided in-depth history of Hawaii), knew all these private spots, super friendly (my two boys kept talking about how awesome he was post the tour) and a superb driver for the twisty roads (my 75 year old mother-in-law sat in the back of the Escalade and was 100% fine)! We visited private waterfalls, had a leisurely swim at the black sand beach, had an awesome lunch of seared local fish, saw a bamboo forest and ended the day watching sea turtles and an endangered seal resting on a beach! Thank you Jack for such an incredible tour!!

Diane K

The road to Hana is intense with all the bridges and turns! The scenery is stunning along this road, so I was glad to be able to sit back and relax to really enjoy the natural beauty. We're so glad we left the driving to Jack. He is an expert on driving the road to Hana and did a great job making us comfortable throughout our day. Out of everything we experienced during this tour, it was Jack's telling of the history of King Kamehameha that we will probably remember most! Jack's storytelling style is engaging and he did a wonderful job of bringing the history of the island to life for us. I have two pre-teens and they both enjoyed the stories, too! I highly recommend riding with Jack!


Great day with Jack! We were a family of 4 including two teens. So glad we left the driving to Jack. His escalade was extremely comfortable and he was so knowledgeable about history and the local area. We learned so much and saw so many awesome sites. He was very prepared - when I started to get a little car sick, he had ginger tabs (and I sat upfront on the way back)! We left early and were able to get ahead of most of the traffic along the road. Had an amazing lunch at a little stand in Hana. Left us a lot of time for beach at Black Sand beach, short hikes, waterfall viewing, etc. Definitely worth every penny. Thanks Jack!


I booked Jack for a Road to Hana tour for my parents — here's what they had to say: My husband and I joined Jack “ The Legend” on a day- long Road to Hana private tour. Jack was a great guide and an expert on Hawaiian history. I will always remember the great risk he took to retrieve the phone that I accidentally dropped out the car window onto the highway. Jack went back more than a mile and was able to find the phone and hand it back to me intact. He literally made my day and saved me a lot of money.

Elizabeth C

Jack was a great tour guide. His history of the Hawaiian Islands was phenomenal. We enjoyed his stories and the places he took us to see. He found food to make the whole family happy.
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2024-06-19 13:08