Maui Road to Hana VIP Private Tour in Convertible Bronco or Jeep

The ride to Hana is beautiful. However I don’t normally complain but I have to say we were disappointed with our guide Raeya. She kept conversation going but didn’t give us much history or stories about Hawaii in general or any of the stops along the drive. Not very knowledgeable and we felt rushed at times. She did not stop at a black sand beach which everyone was looking forward to. When I booked the tour JourneyJill tours sent me a message asking if we wanted to make a stop at Waiʻānapanapa State Park which I confirmed that we did and I was told that they would be happy to arrange the stop. When I mentioned it to the driver she said “we don’t go there. You need reservations”. I visited Maui a few years ago and l learned so much from our Road to Hana guide then and had an incredible time. I was really looking forward to a similar experience. Unfortunately we were disappointed with this trip. A private tour for 4 people is expensive I would expect better service. I certainly hope this is not the norm and that others will receive a better tour.

If you’re looking for an unforgettable way to experience Maui, I can’t recommend Journey Jill (JJ) enough. From the very beginning, she was professional, friendly, and incredibly knowledgeable about the island’s history, culture, and hidden gems. What really stood out was how personalized the experience felt. Instead of a generic, rushed itinerary, JJ took the time to tailor stops based on our interests—whether it was scenic overlooks, local food spots, or quieter beaches away from the crowds. Her storytelling brought each location to life, weaving in Hawaiian legends, historical context, and insider tips you wouldn’t find in a guidebook. Driving the winding roads (especially along the Road to Hana) can be stressful, but Jill handled it with total ease in her open roof Jeep, letting us relax and soak in the views. She also made sure we had plenty of time for photos without ever making the day feel rushed. Beyond the logistics, her genuine passion for Maui really came through. It felt less like a tour and more like being shown around by a local friend who truly loves where she lives. If you want a smooth, enriching, and memorable Maui experience, booking with Journey Jill is an easy choice. I’d absolutely do it again. This was my most favorite Maui memory! !

Shannon was an outstanding tour guide for the Road to Hana! From start to finish, she was knowledgeable, friendly, and incredibly engaging. She shared so much history and local insight that really brought the journey to life, while also making sure everyone felt comfortable and taken care of. Shannon paced the trip perfectly, knew all the best stops, and had great recommendations along the way. Her positive energy and passion for Maui made the experience unforgettable. I highly recommend Shannon if you’re looking for an informative, fun, and stress-free Road to Hana tour!

After planning it for months, at last the Road to Hana, what better than with JJ (few guides in Hawaii speak Spanish), in addition to his interest in people, nature, culture, (local), 'aina; the fame of the route is more than deserved. Thank you JJ for an illustrative and fun day. We've had no time.

This trip was the highlight of our trip to 7 of Hawaii’s islands. Can’t say enough about our guide Josh! He was a great driver, knew the history and took us to a great local place to eat. The Bronco was very comfortable, we had a great view with the top down. Josh made sure we had drinks and snacks to our liking. Highly recommend this trip.

We had the absolute best Road to Hana tour with Journey Jill (JJ)! She picked us up in a beautiful convertible Bronco, which made the drive even more fun. JJ was such an excellent guide—so personable, full of amazing stories from her incredible life, and truly a pro when it comes to the Road to Hana. She took us to hidden gems that only a local would know about, including a hike to a gorgeous waterfall. We grabbed lunch at a delicious food truck and enjoyed it by the beach, then later stopped to see sea turtles resting on the sand. Along the way, we saw some of the most breathtaking scenery ever. She even provided snacks and drinks, which was such a thoughtful touch. As a travel agent, I’ll be recommending JJ to all of my future clients. Thank you, JJ, for an unforgettable experience—we had the BEST time!

Best way for the Road to Hana as got to enjoy the journey with someone who knows the Island, places to stop and eat. Great to have an open top Bronco - magical! Thank you JJ for an amazing day.

We took a Road to Hana tour with Shannon, and it was a fantastic day. We saw beautiful beaches, waterfalls, stopped at local farm stands, and ate famous huli huli chicken.

My wife and I had the pleasure of taking the road to Hana trip with Shannon from Journey Jills yesterday. Great experience!! Your customized to what we wanted to see, and all of it for in prior to our cruise ship departing. They even adjusted the itinerary to leave an hour earlier to make sure all got done and we got back to the ship on time. Waterfalls, black and red sand beaches, swimming, turtles... It was a great day and I highly recommend them. BTW, Sassy was the name of our Ford Bronco that took great care of us on that beautiful but dangerous road. Glad we left the driving to them!!

A year and a half ago I did the Road to Hana with a friend driving who lives in Maui. When I came back with a friend from England in May, I knew we had to go but I definitely did not want to drive it myself. We had an excellent experience even though it became rainy, then actually cold by the time we got to Hana. So the roof was only open for part of the trip. Shannon was our guide. The trip is so beautiful, changing landscapes and seascapes and some beautiful beaches and waterfalls. It wasn’t warm enough for any of us to go swimming. It was wonderful to have someone else drive and to have them find us places not as touristy. It is important to leave early in the morning to get more time/space with fewer people. We liked that Journey Jill was woman-owned, and we could do a tour with just the 2 of us rather than a van full of people. The only negative thing we thought, was our guide reminding us ahead of time, to bring cash for local vendors and also for a tip, she put in parentheses 20-30% for excellent service. We thought it would be so much better if she had just said the usual - for gratuity for the guide, rather than adding 20-30%. I didn’t mind tipping servers in restaurants etc, 30% when I was there in October 2023, 2 months after the fire. But we thought it was not aloha to ask upfront for a specific percentage, especially 30%, because the trip for 2 people was definitely not cheap. We tipped about 20% in the end.