Maui Photos, Part II // Our Road to Hana Itinerary

road to hana three bears waterfall upper waikani falls

Taking a dip at Upper Wailakea Falls (Three Bears Falls) 

While in Maui, we got so much great insight from you guys (via these IG + FB posts) about the Road to Hana. I know the Road is very touristy and a number of you got bored or carsick along the way, but I personally enjoyed it and wanted to share our experience! As they say, the Road to Hana is not about the destination but about the journey. We didn’t find any of the stops individually to be amazing, but the variety of all the different stops along one drive made it unique and worth doing once.

This popular excursion begins in the Kahului region (by Maui’s main airport) and goes beyond the quiet, remote town of Hana on the other side of the island. Along the way are various hikes, waterfalls, and parks amongst dozens of scenic overlooks. The drive itself is only about 60 miles, but due to over 600 winding curves and 46 one-lane bridges along the way (get ready for lots of yielding!), it can take over 2 hours one way not including any stops.

A few thoughts before we begin:

– Start early and take two days if possible. I think the main reason we enjoyed it was because we took our time, and didn’t have to worry about rushing home before sundown. What makes staying overnight tough is there’s a grand total of about 1 main hotel in Hana, so if anyone has alternate suggestions on where to stay along the way, please share!
– Get a GPS-based travel guide to listen to, since there’s no cell service along the way. We bought the popular Gypsy app ($5 on your phone), which was informative and easy to listen to.
– Narrow down and prioritize the stops. Don’t try to do too much!
– Bring lots of bug spray, water, snacks, and motion sickness pills if you get carsick. Also bring secured footwear, whether it’s sneakers or hiking-friendly sandals.
– Rent a Jeep to go all the way around the island instead of backtracking home. Although, do this at your own risk (read more below)!

maui hawaii surfboards extra petite fashion blog

surfboards at Paia town, from this blog post

Paia is actually listed as the first stop along the Road, but we were already staying there. This is a small surfing town so not an eventful stop, but you can fill up your gas tank, and grab some food at Paia Bowls or the well-stocked Mana Foods grocery store.

hookipa beach sea turtles maui hawaii

Sea turtles on Ho’okipa beach // outfit from this blog post

Ho’okipa Beach (mile marker 9) and lookout point – popular with windsurfers for the very strong current, and also known for large sunbathing sea turtles in the afternoon. We visited here but later in the day, not as part of our Road to Hana trip. If you’re passing by en route home before sundown, do stop here for the surfer and turtle-watching!


outfit from this blog post

Huelo Lookout Fruit Stand (between mile markers 4 and 5) – Not a scenic stop, but a tiny shack where you can hydrate with one of their smoothies or fresh coconuts. The “lookout” is just where a short path ends in a forest, so that in itself is not worth stopping for.

Kaumahina State Wayside Park (mile marker 12) – public bathrooms! These can be few and far between, so we stopped at nearly every opportunity.

keanae peninsula road to hana maui hawaii stops

Ke’anae Peninsula (mile marker 16)- a short detour drive along the peninsula. There were huge waves here crashing on black volcanic rock, and a little horse grazing on a farm. We regret passing by the line at Aunt Sandys to get banana bread and pork sandwiches, which you can then enjoy overlooking the waves or stash for later. PS – there’s public bathrooms at the tip of the peninsula!

Upper Wailakea Falls or “Three Bears Falls” (mile marker 19) – This was my favorite stop and where we spent the longest time. You can view the falls from the road, or climb down and get right up and in them.  If we had packed a picnic lunch, I could’ve spent an afternoon there sunbathing on the rocks and dipping into the refreshing water. I expected it to be jam-packed with hollering spring break visitors, but it was so serene with just a few people climbing down every so often.

crouching tiger hidden dragon

crouching tiger-ing my way down to Three Bear Falls – Nick has a knack for capturing me in compromising positions!

If you drive past the waterfall about 100 yards, there’s a small parking area on the left side of the road. You can park there then walk carefully along the road shoulder back to the falls. There’s two openings to climb down on opposite sides of the road – we made the mistake of going down the one closest to the falls (see above). The one closer to the ocean is much less steep! The rocks are slippery when wet both during the climb down and in the water, so be careful and wear your sneakers or water shoes when going down.

maui hawaii road to hana swimming in waterfalls

Pua’a Kaa State Wayside Park (mile marker 22) – public bathrooms! There’s a small waterfall here with a pond, right on the side of the road. We drove by and thought it was perfect for kids to go splashing in without having to hike or climb down any slippery rocks.

Nahiku Marketplace (mile marker 29) – Mr. Gypsy Guide made this seem like a fun marketplace of local vendors and eats, but I don’t think it was worth stopping at. The food and coffee we had was pretty subpar and overpriced.

road to hana black sand beach volcanic caves maui hawaii

Wai’anapanapa State Park (mile marker 32) – large park with a strip of black sand beach, caves, and camping grounds. After checking in at our hotel, we headed here and spent the rest of our afternoon at this park.

Travaasa Hana Hotel – I’ll talk briefly about our hotel since it’s one of the only options in town. It’s not my type of resort, but some might enjoy it for peace and relaxation (the crowd was mostly older couples with a sprinkling of families). Rooms are on the pricier side (starting at $500/night) without AC or TVs, and the resort is more spread out in style, with a walking path as well as golf carts to take you around to tennis courts or pools. The property is situated near the ocean, but it’s over a rocky shoreline and not a swimmable beach.


room and pool at the Travaasa Hana

travaasa hana resort hotel where to stay maui hawaii

Hana Town – We kept reading that Hana is a small sleepy town. Therefore we weren’t expecting to do much, but were still completely unprepared for just how limited the food options were! Don’t rely on the operating days and hours listed online, since places close when they sell out. I had been eagerly awaiting some Thai food from one of the two popular trucks there, so was crushed to find out both had closed early. By 6PM, the only place open in town was our hotel restaurant (with dishes starting at $50 and very mediocre reviews) … such despair!

troys plate lunch food where to eat road to hana

Troy’s plate lunch // BBQ pork + shrimp-stuffed parrotfish (which Troy catches himself!)

A lack of good food options puts a damper on my day, so imagine waking up the next morning and still not being able to find anywhere open to eat at! Poor Nick had to deal with my “hangriness” (or more accurately, cheapness, because I refused to eat again at our hotel). After driving around, we stumbled upon Troy’s Plate Lunch setting up early. This husband and wife team cook everything in the morning off-site, so I’d stick to items that keep well in hotplates like BBQ or Korean chicken, and avoid fried items which wouldn’t be crispy anymore. We got the first serving of the day so everything was at its prime, and pumped new life into me!

There are even fewer food options past Hana, so if you’re continuing on that way and didn’t pack enough snacks, be sure to grab something first.

haleakala national park pipiwai trail bamboo forest road to hana maui

 Zella live-in leggings xxs (hemmed), Nike Free sneakers (size up)

 Haleakala National Park (mile marker 42) – home of the Pipiwai trail and the Seven Sacred Pools. The parking lot was packed by late morning, however we didn’t see many people on the trail after the initial stretch. The parking fee is now $20 per car, but it also includes access to the Haleakala crater summit (except at sunrise, for which you need to get a permit in advance) so save your receipt.

pipiwai trail waterfall road to hana maui

Waimoku falls at the end of the Pipiwai trail

The Pipiwai trail is about 2 miles each way, and took us about 2 hours round trip. It goes by a big banyan tree, streams, overlooks, and then a long stretch of bamboo forest. At the end of the trail is the tall and trickling Waimoku falls, which we honestly didn’t find impressive on that day, but we also didn’t venture off-trail to get closer. Overall I thought the hike was pretty easy for the non-athletic like myself (just remember to bring plenty of water!), and the bamboo stalks whispering in the wind were relaxing along the way.

road to hana hiking bamboo forest palm leaf print bikini swimsuit

Sadly, the Seven Sacred Pools were closed for swimming so I had no use for a swimsuit. Not being one to pass up a photo op, I pulled my leggings down by my ankles for a picture and may have scared off some passerby hikers who thought I was popping a squat ; )


The Road Home (along the backside of Haleakala)
From here you’ll have to either backtrack home along Hana Highway, or continue going around the island, which we opted to do. We were told: 1. You need a Jeep to drive around the back roads, and 2. rental car agreements are void if you go that way. So a Jeep definitely helps, and what the rental clause usually means is you’re on your own out there in the case of car troubles.

Our cameras couldn’t come close to capturing how vast and serene it was. The landscape changes significantly from oceanside cliffs, to dusty unpaved roads, to rocky terrain and cattle farms. We didn’t have cell service and there were long stretches without another soul in sight, so any car issues would be a nightmare. At one point I misunderstood Nick muttering and thought he said we were “breaking down,” to which I had a mini panic attack, envisioning ourselves being stranded out there for days before becoming food for mongoose (vicious little things that look like squirrels)!

surfing baby goat dairy farm maui hana

Surfing Goat Dairy – As you’re approaching the main part of the island again, there are a few attractions off the back roads including a goat farm, winery, vodka distillery, and lavender farm. I was curious about all of these, but when forced to prioritize, it wasn’t hard to choose the baby goats! I read the “farm tours” were not worth it, so we just watched and pet the adorable babies, then ordered a cheese plate and some chocolate truffles. I actually am not a goat cheese fan at all, but the ones on the platter were mostly mild and admittedly very good – a yummy end to our two-day drive!

surfing goat dairy farm cheese charcuterie platter where to eat maui hawaii

I hope you guys enjoyed this post! Let me know what stops we missed along the Road to Hana that you would highly recommend to visitors!

Other posts from this trip:
Paia apartment rental review + photo journal
Outfit post at Back Sand Beach
Outfit post in Paia
Outfit post at Wailea Beach

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  1. Arista Pi wrote:

    You and your hubby are beautiful sweetheart! I love the Asian love (assuming he's partially Asian?) Either way good looking out girl. I've always seen your gorgeous pictures and super cute fashion sense on Pinterest and finally found your blog. You're so pretty and tiny and I love that you're representing for us! Keep up the great work, your outfits definitely inspire me, I especially love those high waisted wide leg pants on you, I think they were like a way older post and possibly Anne Taylor? Can't wait till it's warmer and see what you incorporate into your wardrobe from S/S17 ❤. You are my favorite preppy/girlish/sophisticated fashion goddess!

    Posted 5.9.17 Reply
  2. Lauren wrote:

    Jean, Thank you for your suggestions. They worked! I really felt like I was getting the 'run around' before. I now have my skirt, delivered Friday. Your intervention is very much appreciated!

    Posted 5.7.17 Reply
  3. I love Maui and have been there over 10 times. =) But, your photos StiLL make me want to go back, they are so lovely. I always find Maui SO casual and feel over dressed everywhere I go. However, your beautiful outfits put me to shame. LOL. Next time I'll be more brave. Thanks for the inspiration. Mahalo

    Posted 5.4.17 Reply
  4. Such gorgeous photos! I love all your bathing suit choices.
    Julia・Little Miss Haute Couture

    Posted 5.1.17 Reply
  5. Kirsten wrote:

    i LOVE that guy eating your dress! the waterfalls are beautiful <3

    -Kirsten //

    Posted 5.1.17 Reply
  6. Love this! Maui looks incredible!
    I'm also in love with your leaf printed swimsuit!♥

    Posted 5.1.17 Reply
  7. Denise W. wrote:

    I explained to my husband who you are….educated, career-oriented, blogger….and then I showed him the bathing suit/leggings narrative. When he got to "popping a squat," we were both reduced to tears. You are funny!
    Oh, I also hate goat cheese. It smells like feet : ( Carry on, adorable lady!

    Posted 4.30.17 Reply
  8. Anonymous wrote:

    Hi Jean! I've been a longtime reader (since 2012, maybe?) and have enjoyed seeing your style evolve over the years. We're probably around the same age and pretty much learned how to dress for work from your blog! I've lived on Maui my entire life and it's so interesting to see it from your perspective! You look glamorous even in your casual attire 🙂 Also, I'm impressed you ate at Ichiban Okazuya… it's such a small little hole-in-the-wall spot frequented by mostly local families and the workforce in town. Loved how you highlighted all the beautiful spots on Maui in these travel posts!

    Posted 4.30.17 Reply
  9. Jean wrote:

    Hi Joann, I'm not a representative of Chicwish, but I do care about your poor experience because I'd very be frustrated as well. I really like some of my items from there, but think their customer service has room for improvement.

    From my own shopping experiences at Chicwish, you have to be adamant with follow-up emails and very firm. Once I sent a return back and they only gave me store credit saying I mailed it after the return deadline – I wrote that was definitely NOT the case, and got a full refund afterwards. If you haven't already, I would email them again and ask for the replacement to be shipped out right away (and ask for the estimated delivery date), otherwise say you'll file a dispute with your credit card company or Paypal, etc.

    I've sent lots of customer service feedback to Chicwish and they have (believe it or not) improved over the years, unlike some other companies that don't care about customer service or don't even respond to emails. I've always received my orders or gotten a refund on returns, however it can take a long time which is something they really need to work on. I've sent them an email too about your exchange, but please keep me posted about how it works out.

    Posted 4.30.17 Reply
  10. Jean wrote:

    Ah sorry I forgot to include that – it's from H&M;!

    Posted 4.30.17 Reply
  11. Jean wrote:

    Thanks for the tip, Kim! I have a few kids leggings from various places too, including H&M; and Gap. I'm a Zella convert because the material actually holds incredibly well through running / travel, and doesn't stretch out or bag at the knees over time.

    Posted 4.30.17 Reply
  12. Jean wrote:

    Yum! That's a great idea…

    Posted 4.30.17 Reply
  13. Jean wrote:

    Thanks! It's from H&M;!

    Posted 4.30.17 Reply
  14. Unknown wrote:

    Our party of 3 adults and 1 toddler stayed at Hana Kai Maui, which was fabulous. After landing in Maui, we stocked up at the nearby Safeway. We cooked dinner and ate it on the lanai overlooking the ocean. For the rest of our stay, we hit the food trucks at Hana.

    Wanted to see more photos of the area where most people turn around (backside of Haleakala). We were too chicken to try that. =)

    Glad you had a good trip!

    Posted 4.30.17 Reply
  15. Posted 4.30.17 Reply
  16. Mizeats wrote:

    Glad you had a wonderful time in Maui! Thank you for providing this helpful itinerary. These pictures really capture the beauty of Hawaii. I can relate about needing good food options while traveling! It's one of the things that's tops on my list when visiting too!!

    Posted 4.30.17 Reply
  17. Joann wrote:

    You have featured Chicwish clothing several times on your awesome site! I purchased a jacket last fall and just love it! I also purchased a blue/white (Marine Midi) striped skirt this spring for Easter. Unfortunately, it was too big, so I returned it for a smaller size. I shipped it on April 7th; received by Chicwish on the 10th. To date (April 30th), I STILL do not have my skirt! I did send an e-mail to them, asking when I might receive the new skirt. I had clearly marked what size I needed in exchange; however, they wrote back asking me what size I wanted (is this a stall tactic?)! They said it "still needs a few days to be restocked. We will process and reship it asap once it is restocked." How long does it take to 'restock' a returned item and resend? I find this questionable and disturbing since they are quick to ship out when you order something! My question to you: Are you still continuing to represent their clothing line? If so, I thought you should be made aware of the fact that they now have my money and my skirt!

    Posted 4.30.17 Reply
  18. Olivia wrote:

    wow these pictures are beautiful! Love it! New post/

    Posted 4.30.17 Reply
  19. Thai wrote:

    great photos! i wondered where the retro high waisted bathing suit is from, in which it had not been linked?

    Posted 4.29.17 Reply
  20. Kim wrote:

    Love reading about your adventure. Note on leggings, I found gap kids full length leggings on their site right now to fit well, good quality, solid black, back pocket, high waisted, inseam not too long, no camel toe, machine wash, affordably priced, recommended for extra petites! A reviewer said it's the same quality as the women's version. The silhouette could be more figure flattering but they look pretty good considering fit and price and quality and machine wash. The cropped version I thought was too cropped, not 7/8 length although limited sizes were available in store, maybe I could have sized up.

    Posted 4.29.17 Reply
  21. Thanks for all the tips! You have amazing outfits and perfect pictures as well!


    Posted 4.29.17 Reply
  22. Isabelle wrote:

    Amazing photos!
    XO Bella,

    Posted 4.29.17 Reply
  23. hlo wrote:

    We had the same hunger problem on the north side of kauai, esp bc we're night owls. When on road trips abroad we've taken to bringing larabars, buying baguettes/cured meats and swiping some butter/mustard packets from breakfast.

    Posted 4.29.17 Reply
  24. Amazing photos!! I definitely want to do this trip now, it looks amazing

    Posted 4.29.17 Reply
  25. Anonymous wrote:

    Great travel shots and tips. What is the brand of the high-waisted bikini you wore at Pua'a Kaa State Wayside Park?

    Posted 4.29.17 Reply
  26. Jean wrote:

    Oops! Thanks for pointing that out.

    Posted 4.29.17 Reply
  27. Wonderful photos, Jean! It looks like you had the absolute best time in Maui! I hope you have a lovely weekend!


    Posted 4.29.17 Reply
  28. Anonymous wrote:

    I think there's a typo: Seven Sacred [misspelled Sacred] Pools.

    Posted 4.29.17 Reply
  29. You've worn such appropriate outfits for the activities you did! 🙂 Super cute!

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 4.29.17 Reply
  30. La Bijoux Bella | by mia wrote:

    Simply beautiful photos … so peaceful scenery! 🙂

    Posted 4.28.17 Reply

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