Horseback Riding and Talking Story in Hana

By Mr. TWS

Among the many varied experiences during our recent trip to Maui, one of the most memorable was horseback riding in Hana, on the island’s eastern coast.

"Waves break along the Hana coastline in Maui"

Morning on the Hana coastline

Horseback riding on Maui

Though Sweeney had done some English style riding years earlier, my experience had been a few rides on a friend’s horse; in that the goal there was not to learn to ride but to survive. There are coastal horseback rides in California very near our house, but we’d never chosen to try, partly because there had been some controversy regarding the treatment of the horses. Both of us were quite happy with the decision to ride in Maui: even with our history, riding was basically a new experience, the views along the coast were perfect and so was the weather, but probably the biggest reason was the surprise we hadn’t expected.

"Lucky and Cody await their riders at Hana Riding Stables in Maui"

Lucky and Cody

As we approached the Hana Riding Stables, just across Hana Highway from our cottage at Travaasa Hana, we were greeted by our guide, Jolynn Piimauna, who introduced us to Lucky and Cody, the horses Sweeney and I would ride. We were especially lucky to be the only ones taking advantage of the early morning ride.

"Jolynn of Hana Riding Stables instructs Sweeney"

Jolynn giving Sweeney instruction before the ride

As with anything new, there’s always a little apprehension and a desire not to do anything stupid. Jolynn was very calm and instructive and seconds later Sweeney was up on Lucky. Jolynn provided the basic instructions for holding the reins, leg and body positioning and then basic ways of communicating with Lucky to go right, left and stop. It was here we got our first insight about Jolynn. Sweeney said, “And you’ll be right there with us.” Jolynn said, “No, I’ll just need to go with you to cross the road and then you’ll be on your own for the ride; just be back in an hour.” We were both surprised.

A surprised and frightened rider?

"Is this a frightened rider on Lukcy the horse at Hana Riding Stables in Maui?"

Shocked by the news?

I thought that was unexpected, but pretty neat. Judging by the look on Sweeney’s face, I don’t think she was fond of the concept she but she just laughed and said, “Oh, OK!” (The photo above was just a random shot.) Then quickly Jolynn said, “No, I’ll be with you all the way.” I really appreciate that kind of tongue in cheek humor and have a pretty good radar but Jolynn had taken us both. It was the timing and total believability of her delivery. Seconds later I was up on Cody and after the same instructions, we were off.

We crossed the road and headed into a pasture along the coast. There were other horses there and a younger one was in the path. I assumed Cody would just walk around on his own but headed right for the horse nipping him in the butt as if to say, “Get out of the way, youngster; show some respect.”

"View of Hana coastline while riding on horseback, Maui"

Hana coastline

The Hana Ranch owns lots of property near Hana much of it is used for raising cattle. We approached a gate and could see many “cows” on the other side. Jolynn said, “They’re all bulls. They’re used to riders coming through; they won’t bother with us. Just don’t look them in the eye.” It was only when I’d repeated this for Sweeney that she told me she was just kidding. Twice in a few minutes; Jolynn was one of the best at this.

"On horseback along the Hana coast, Maui"

Traveling with Sweeney on horseback

Talking Story

The Hawaiians have a term for chatting and story-telling, “talk story”, and that’s what we did about several different topics during the beautiful ride along the coast just south of the Travaasa property; we learned a lot about Hawaiian (in particular Hana) residents and also about Jolynn who was the surprise of the trip making what would have been a great activity into one that was really extraordinary. She talked of her upbringing as a fourth generation Hana native and her father who trained horses teaching her at an early age. She first rode a horse alone at two. She said she and her four siblings didn’t understand why they couldn’t play and take it easy like other kids but now she is really grateful that her father passed the family business to her siblings and especially her. She was a living representative of the way tradition and lore and know-how are passed generation to generation uniquely in Hawaii.

Along the way, Jolynn pointed to a large house that was far out on a point and said there was a 90+ year-old woman living there. She said that the woman gave back to the community by allowing the locals to use a section of her property for parties at no cost for special celebrations, such as weddings. In return, volunteers donated time to help with the upkeep of her property and house.

Jolynn talked about other ways that people helped each other and how this community of about 1800 residents was a very close knit family. The downside, she said, is that everyone knows your business. She talked of her sister’s house being destroyed by a tsunami. Townspeople on higher ground pulled her mother and sisters from the water to safety after the first wave. The townspeople also worked together in restoring their home, which was completely gone after the wave, and they did it in less than a month.

"Travaasa Hana cottages, previously a sugar plantation in Hana, Maui"

Travaasa Hana, previously a sugar plantation

Jolynn said the pastures had been a sugar cane plantation and the Travaasa buildings were the buildings where 500 had workers lived. When the plantation was purchased in 1946 the buildings were renovated and additional ones added to later become what is now Travaasa Hana today.

She spoke of the high cost for groceries and the fact that locals would make monthly treks to the other side of Maui to stock up and freeze food and supplies that are far less expensive than in Hana. She said they supplement with meat they get by hunting deer and wild pigs on the freely accessible land as well as by fishing in the ocean. There were also stray cattle that were considered wild.

We had heard that Oprah Winfrey owned property that we would be riding near. We had just assumed an investment but Jolynn described meeting Oprah as she inquired about Hana, and Jolynn also provided the “rest of the story” (as Paul Harvey used to say). She thought Oprah was a wonderful person and described the land deal as something that really helped the Hana Ranch and the community. She also described Oprah’s generosity and friendliness towards her personally.

We asked about other celebrities she’d met and she mentioned a few such as Michael and Janet Jackson, Steven Seagal and Jim Nabors. She particularly singled out Michael Jackson, saying that he was so incredibly nice. When her family heard he was to take a riding tour with her, they all wanted to show up and meet him. When she asked him if it would be OK, he said certainly and was very gracious with his time after the ride, spending hours listening to her sister singing country western songs (a tradition passed on by their mother) and joining in. She said they were all very nice, but did mention one other celebrity who was not so nice and very demanding. However, Jolynn made it clear that she was the boss on the trail ride and the celebrity needed to do what she said.

"Jolynn at Hana Riding Stables, Maui"

Jolynn and Sweeney

The ride and instruction were great, but the really surprising and unique aspect of the activity was meeting and talking with Jolynn. If you travel to Hana, take the time to go riding with her. Check with Travaasa Hana’s concierge about Hana Riding Stables pricing and reservations.

Talk story with us — what are your horseback riding experiences?

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49 thoughts on “Horseback Riding and Talking Story in Hana

    1. Mr. TWS

      Thanks for the comment. Given the fact that she let us know on the first 2, I’m certain the rest of her anecdotes were authentic. She is an admiral person, particularly based on some things Sweeney edited out because they might be too personal. But Jolynn was quite representative with the behavior of help your neighbors and do what you can when you see need.

  1. Fida

    This is still one of my dreams that I have to give life to… Riding horses in Hawaii. I am green with envy. It took a long time for me to warm up to horses. Growing up on an Alpine farm all I knew where enormous work horses with backs the size of a small car. They sat us children on their backs while crossing rivers that were too wild to let us jump from stone to stone… I held on to dear life and seeing the water flowing beneath didn’t help either. It wasn’t until a few years ago when my good friend and horse whisperer gave me riding lessons on his quarter back horse. My fear turned to instant love 🙂

    Love the Talking Story and dead-pen Jolynn. I hope she’s still willing to let me ride one of her horses, now that she’s accustomed to Oprah, Michael and the likes 🙂

    1. Mr. TWS

      Thanks for the many comments. To your last paragraph, she took US, so I wouldn’t worry.

      Thanks for sharing the childhood memory; It does sound scary.

      I hope you are able to make it to Hawaii soon; be sure to try horse riding; I think any of the major islands have riding but Jolynn in Hana, Maui would be a good choice (Maui, Oahu, Kauaii, Hawaii, Moloka’i).

    1. Mr. TWS

      I wasn’t able to tell that the horses liked either of us; they were just well trained. I felt that Cody was not over pleased with having the heavy load. However, he did turn back and watch us as we walked away. It might have been a goodbye; or maybe a good riddance. Thanks for the comment.

  2. Suzanne Fluhr

    The last time we tried horseback riding was in Costa Rica and it was very scary. Your ride sounds like it was very pleasant. If we return to Hana, maybe we’ll give horseback riding another try.

    1. Mr. TWS

      I hope you do. This was a completely non-scary ride but exhilarating because of the setting and views. I think part of it had to do with the calmness of the horses. The choices for us were used for beginners and I think the love that Jolynn expressed for her horses and provided in their care and training resulted in their calm demeanor.

    1. Mr. TWS

      I hope you get the opportunity soon. The horses were fun and very well trained. When my horse rubbed his face on Sweeney’s leg to scratch, I didn’t pull it away because knew she would be okay, though it did make her a bit nervous. Thanks for the comment.

  3. Barb

    One time when a friend and I were riding we decided to have a little race on the bridle path. When we came around a curve there was a huge puddle of water covering the path. Turns out the horse I was riding wouldn’t go through water. When he saw that puddle he stopped dead and I went sailing through the air over the puddle and onto the cinder path. OUCH!

    1. Mr. TWS

      We certainly never moved that fast. That seems one of the real dangers in riding. Scary story; glad you survived ok. You must have been a pretty good rider. Thanks for the story.

    1. Mr. TWS

      She WAS a real hoot and the ride was beautiful in a very peaceful setting. I think the horses are also very good because of Jolynn. So it would be a good choice. Hope you are able to do it soon. Thanks or the comment.

  4. noel


    Hana is a beautiful area in Maui, its always fun to do something special like horseback riding in this lush area. Thanks for sharing your journey.


  5. Gaelyn

    I owned horses once and loved to ride right out of our gate My horse side-stepped a rattler and so did the horse behind. So glad.

    I’ve never ridden on the beach and that sounds like fun. But the best part seems to be Jolynn.

    1. Mr. TWS

      This ride was more in a pasture right above the coast. But Hawaii does have some that are beach rides. I think I’ve seen that scene with rattlers in a number of Westerns. Usually they don’t end well for the rider. It sounds as though your horse was pretty smart and considerate of its rider. Jolynn had horses that matched the skill of the rider and I’m sure the others would also. That image of riding on a horse speeding along a beach splashing in the water has always seemed to me to be one of those great things to be able to do.

    1. Mr. TWS

      At first, I thought you were pulling a Jolynn. I never heard of a horse allergy. Sorry it spoiled your ride. It really seems to be a fun way to see some beautiful sights. There was a mule ride down a steep cliff in Moloka’i to get to one of the most famous sights there, the Kalaupapa Peninsula, the place where lepers were banished and later ministered to by Father Damien, who contracted the disease and was sainted. You could also walk the path if you signed for the tour and I would have loved to see the scenery but we were surprised the whole activity would have taken about 7 hours, hiking or on mules, and didn’t align well with the limited travel options to the island and out tight itinerary…next time. Thanks for your comments.

  6. Steve

    I think when Jolynn said she wasn’t going with you I would have been down off my horse and back in the car before she had the chance to tell me she was joking. Looks like a beautiful way to see the coastline though.

    1. Mr. TWS

      It was a great way to see the views and the ride was fun but it was worth it just to talk story. Your response to the joke would be the logical one. Thanks for the comment.

  7. Barbara Sheridan

    We traveled to Hana in Maui last summer and stayed at Travaasa . It was so amazing and we saw the horses out in the pasture by the ocean. Next visit we will plan to do horseback riding. I do plan a visiting again.

  8. Iliki Kanakoa

    Thanks for this story. My husband and I were married on Kauai in 2007. While we were on Kauai, we went horseback riding and it was wonderful! I have always loved horses and I am a fairly good rider. My husband told me and our guide, Bob, that he was a good rider too. Of course we believed him. Somehow Gene wound up as the last rider of the three of us. We were riding across fields of pastureland and trails through forests. It was so beautiful. I wanted to gallop, and Bob gladly agreed to do so. So we went flying through the fields and valleys and it was glorious. We rode for three hours and after an hour and a half, we stopped for the lunch of sandwiches and mangos, pineapple, papaya and other of Hawaii’s wonderful fruits that Bob had prepared for us. Then we went swimming in a freshwater spring complete with a small waterfall to cool off because the sun had come up and it was hot. During the ride back to the ranch (and I can’t remember the name of it— I will have to get out all my memorabilia from that magical trip to Hawaii to find out) Bob told us stories of Hawaii and also of his own life. He was from Detroit. He had gone through a bad divorce and afterwards had sold everything he owned and flown to Hawaii. He was very disappointed when his plane landed in Honolulu, because he felt like Honolulu was very much like a big mainland city. Someone had told him to go to Kauai, the garden isle, if he wanted more rustic living— and he found his home on Kauai. He worked for the ranch leading horseback rides and all kinds of other things too. He took us to a Polo Match after our ride. We learned that polo is a big sport in Hawaii. It was so much fun!!!! Later Bob told us that he was a singer with a band and that night we went to hear Bob and his band perform. The people who live in Hawaii are so friendly. They invited us into their lives— and we gladly accepted the invitation. Bob told me that I should move there because I fit in so well. He said I wasn’t like a Haoli at all—but rather like a real Hawaiian! I don’t know if he tells everyone that— but that was the biggest compliment I have ever been given. I was having so much fun that I didn’t notice how miserable my poor new husband was. As it turned out, he really didn’t know how to ride at all— and he had been hanging onto his horse for his dear precarious life during our three hour ride! He was so angry at me for encouraging Bob to gallop for most of that ride. I certainly should have paid more attention to his feelings, but I guess there is a moral to this story and that would be that one shouldn’t tell lies about their abilities because others may take them at face value— and then they could be in real trouble! I am no longer married to Gene because as it turned out, he told a lot of lies and he expected me to divine the truth of what he “really meant” and of course I couldn’t do that— so we were both miserable throughout our five year marriage. But I fell in love with Hawaii, and one of these days I will move there because I left a big part of my heart there.

    1. Mr. TWS

      Thank you so much for “talking story” with us. Your well told memory was much enjoyed by Sweeney and I. Sweeney and I had our honeymoon on Kauai and also celebrated our tenth anniversary there and it is also a wonderful place and special for us. We are long overdue getting back.
      I thoroughly enjoyed our ride but the thought occurred to me about how much fun it would be to know how to ride well enough to really run the horses. As much fun as we had, yours sounds like a really special activity. Bob’s service sounds pretty good so he must still be in business. I’m sure he would really appreciate reading your comments and retelling.
      The Hawaiian people are really special. And reading your story, I’m sure Bob’s comments about your fitting in were not gratuitous and were not said to more than perhaps a few people.
      I totally agree about being honest, not just about one’s abilities but always. With your strong feelings, I hope you find a way to move to Kauai. Knowing what you really want to do is really the hard part and you’ve got that covered. Thanks so much for commenting and sharing your story.

  9. Mary {The World Is A Book}

    What a beautiful experience and often times, it is the people that you meet that makes it even more amazing. Thanks for sharing Jolynn’s story and life in Hana. We only made it to Mile Marker 8 in hana but would love to see Hana on a return trip. It’s a great way to see the coastline and we haven’t done this exciting adventure yet either. Looks so fun!

    1. Mr. TWS

      I am more positive about the trip to Hana after this experience. Staying in Hana even for a day really makes it more reasonable. There are a number of great hikes with beautiful scenery and taking the southern way back really added too. Particularly seeing the running of the bulls (I know you read but for others it’s described in my post – Maui Road Trip: Running of the Bulls)

  10. Sophie

    Riding in Hawaii sounds fabulous and love your guide and her sense of humour.
    I hired a horse in Lesotho – gosh, it’s been nearly 15 years… just me and the horse riding about in the mountains all day long. Very peaceful.

    (ps Always been curious as to why Americans say ‘horseback riding’ instead of just horse riding…)

    1. Mr. TWS

      That sounds like quite a ride and I can imagine very peaceful. I wish I were enough of a rider to do that solo but even with a small group, I’m certain it would have been enjoyable and peaceful (although somewhat less I suspect).

      The comment about horse-back riding is funny. I never noticed it until I wrote the post and it seemed odd and almost made the switch but decided to keep it in the terms I would normally have used in speaking. But I appreciate you pointing it out.

  11. Leigh

    I am a nervous, apprehensive & easily frightened horseback rider who prefers to go no faster than a walk. My most memorable ride was a 3-4 hour affair in Costa Rica through the rainforest where my horse was up to his knees in mud. We climbed thousands of feet and I felt like the ride would never end. My husband on the other hand had a brilliant time – and loved every minute of it.

    1. Mr. TWS

      It sounds an interesting way to see the jungle. Sorry you didn’t enjoy it more. This Hana ride sounds perfect for you. Thanks for commenting.

  12. Abby

    Gorgeous!! I just this year got over my fear of horses. Now I can’t believe how many horseback rides in pretty places I passed over. So fun — you look like a natural!

    1. Mr. TWS

      Thanks for the comments. It was fun. Great way to see pretty places. Hope you get to enjoy some riding in some of them soon. I thinks its one of those things we’ve passed on too and will be more likely to do in the future.

  13. Sofie

    When I was a child in my hometown, my grandparents used to have horses on their farm, my favorite one looked like Cody on your photo, I thought she was a unicorn:) unfortunately, once I fell off her and broke my hand andI’ve never ridden her anymore. Maybe I should give riding one more chance, but then, I have to face my fears.

  14. Pingback: A Maui Resort Sampler » Traveling with Sweeney

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