Wailea Tours
Private Halfway to Hana Tour

Private Halfway to Hana Tour

By Maui Legend Tours
per group (up to 6)
Lowest price guaranteeReserve now & pay laterFree cancellation

Ages 0-120
Duration: 4h
Start time: Check availability
Mobile ticket
Live guide: English

  • Snacks
  • Bottled water
  • Soda/Pop
  • Air-conditioned vehicle
  • Private transportation
  • Pickup and drop-off service at all the hotel resorts and most condos (excludes Travaasa Hana Hotel)
What's not included
  • Beach towels
  • Sun block

Start:Multiple pickup locations offered.
    Pickup details
    • We pick up and drop off at ALL the hotel resorts and most condos, except the Travaasa Hana
    Hotel pickup offered
    During checkout you will be able to select from the list of included hotels.
      Port pickup offered
      During checkout you will be able to select from the list of included ports.
      • Kahului & Lahaina
      End:This activity ends back at the meeting point.

        • Not wheelchair accessible
        • Pushchair accessible
        • Near public transportation
        If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 64704P11

        • Confirmation will be received at time of booking
        • No heart problems or other serious medical conditions
        • Most travellers can participate
        • Not recommended for 6-months-or-more pregnant travelers
        • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
        • This is a private tour/activity. Only your group will participate

        • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

        If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 64704P11

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        About the operator
        Don’t take it from us – here’s what people have to say about this operator:
        • Maui Legend Tours
          Kula, United States
          Joined in September 2016
        • 873leahv
          0 contributions
          5.0 of 5 bubbles
          A wonderful and memorable day
          We had the most wonderful tour with Jack the Legend! We got to see so much on our day tour... starting with part of the road to Hana, with awesome stops along the way, a little hiking, lots of photos, just amazing scenery and windy roads (glad he was driving!), the lush vegetation is so cool with unique features like the rainbow eucalyptus trees, bamboo, and so much more. Then we visited amazing beaches, we saw a large group of turtles resting on the shoreline, beautiful sand and water. We tour some of the up country with amazing views of neighboring islands. We stopped at a little local food place right along the road, delicious! And also visited 'Iao Valley State Monument, wow that place is incredible. We still had time to visit a beautiful, peaceful beach and do some swimming for a couple hours! It was an amazing day and Jack was the best storyteller as we were all enthralled with the history of the island and how it became as we know it today. We had lots of treats and beverages to enjoy long the way. Lovely day and highly recommend!
          Written 12 March 2024
        • Cin214sports
          0 contributions
          5.0 of 5 bubbles
          Jack of Maui Legends. Wonderful tour with awesome tour guide.
          Enjoyed Jacks interesting stories about Hawaiian culture. We saw huge turtles, waterfalls, wonderful scenery! Great tour guide. Loved this tour!
          Written 11 December 2023
        • 22le_lal
          0 contributions
          5.0 of 5 bubbles
          Awesome day as a family!
          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.
          Written 3 January 2023
        • Grace L
          0 contributions
          5.0 of 5 bubbles
          Amazing private tour experience!!
          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!!
          Written 25 December 2022
        • Diane K
          0 contributions
          5.0 of 5 bubbles
          Great experience!
          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!
          Written 13 July 2022
        • 581jennys
          0 contributions
          5.0 of 5 bubbles
          Worth every penny! Family tour on road to Hana
          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!
          Written 25 April 2022
        • 208sauls
          0 contributions
          5.0 of 5 bubbles
          Good times with Jack
          My wife and I had driven the road to Hana 25 years ago... We wish we would have known about "Jack the legend " then. He made the drive with our 13 year old daughter fly by with his historical perspective and side bar stories.. We consider Jack more than a guide!!! He is a friend and a traveling companion when you need it most!!! Thanks Jack for giving us a great day AS ADVERTISED!!!!!!!!!
          Written 30 December 2021
        • waseemio
          0 contributions
          5.0 of 5 bubbles
          Went above and beyond
          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.
          Written 24 October 2021
        • Kelly H
          0 contributions
          5.0 of 5 bubbles
          Amazing Day🌞
          Our family of 6 (kids ages 15,14,14, and 9) took the elite private tour with Jack. We wanted to go on the road to Hana but did not want to drive ourselves. If you want to go to Hana, have an experienced driver, hear the history of Hawaii and how it came to be, stop at the best stops, and have some flexibility- Jack is your guy! He is AWESOME! Jack picked us up at our resort in kaanapali, took us on an adventure, and brought us back with knowledge, pictures, and memories that our family will not forget. Jack should write a book! So happy we chose him. Thank You Jack! It was AWESOME🤙🌺🌈🌊🌴🐢🌞🍍
          Written 13 July 2021
        • Elizabeth C
          0 contributions
          5.0 of 5 bubbles
          Road to Hana: great experience
          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.
          Written 12 July 2021
        • PhilNPeg
          0 contributions
          5.0 of 5 bubbles
          Road to Hana veteran, best trip yet!
          We’ve travelled the “Road to Hana” several times. Driven it twice. Rode once in a 12 passenger van on a tour. This time we took the private tour with Maui Legend Tours. Our guide was Jack, he’s been in Hawaii since 1979 and knows a lot of the history and local culture. We found his knowledge of Hawaiian history and his ability to share it very pleasurable. He stopped at multiple sites along the road and gave us ample time for pictures. This was a “high end” tour in an Escalade and we enjoyed it immensely.
          Written 10 February 2020
        • Letha A
          0 contributions
          1.0 of 5 bubbles
          Might have enjoyed it, had we been able to go.
          Back in November 2018 we made a reservation for this island tour. Received the email that we were confirmed for April 30, 2019. We were so excited to go. Less than two weeks before our tour date I received an email that the tour date was "over-booked" and we'd have to change dates. Seriously, how could they be "over-booked" when we were confirmed 5 months prior?? We were told we'd have to go on Sunday, April 28th, but we had already made other plans for that date, so we ask to switch to Saturday April 27th. While sitting in the airport in San Francisco on Thursday, April 25th I got a phone call that they couldn't take us on the group tour that day BUT..if we wanted to pay MORE MONEY we could get a "private tour". I politely told them to FORGET IT and requested a refund. To say I was angry was an understatement. This is the poorest agency I have ever booked with..and I've been to Hawaii 7 times and taken MANY tours. Will never book with them again. Glad others seem to have enjoyed the tour. Wish we could have.......
          Written 7 May 2019
        • Brad L
          0 contributions
          5.0 of 5 bubbles
          A great day in Maui
          Jack was the perfect guide and host; knowledgable and professional. His pace and narration were spot-on. Granted, weather can make a difference, but on Maui, rain tends to pass quickly and after a couple of short showers, we were back to perfect conditions. If you want to experience Maui away from the resorts and learn about the island's history, this is the tour I would recommend to family and friends.
          Written 5 May 2019
        • 0Loulouk
          0 contributions
          5.0 of 5 bubbles
          Interesting and informative tour of a beautiful area
          Jack was a great host who provided a detailed commentary of the legends and history of Maui. He stopped at beautiful sights and pointed out details along the way. He drove the challenging route with confidence allowing us to focus on the surroundings. The company was helpful and accommodating when a change of plans was required. Highly recommended.
          Written 4 May 2019
        • cmburns47
          0 contributions
          5.0 of 5 bubbles
          Road to Hana tour
          Six travelers had a private tour with Jack "the legend". Terrific day ! Jack was very knowledgeable and entertaining . Really a Hawaiian history lesson. Excellent value, emirable day!
          Written 17 April 2019
        See all 28 reviews
        These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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        5.0 of 5 bubbles1 review
        Very good

        Chattanooga, TN10 contributions
        5.0 of 5 bubbles
        Our trip with Jack was informative, interesting and educational. He certainly knows his stuff, and we were treated to a delightful trip halfway to Hana. Jack is well-versed in the history of the region, and he is knowledgeable about all things related to the experience. Highly recommend!
        Written 8 May 2024
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

        Private Halfway to Hana Tour provided by Maui Legend Tours

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