Only on Maui can travelers swim in waterfalls, hike a volcano, surf breaks, and make it back to their condo in time to toast the day away with chicken katsu, mac salad, and a Mai Tai.
The Valley Isle was a place I've heard so much about but have never actually visited myself. I wanted to do it all – I wanted to try the best banana bread, drive both scary one-lane highways, taste the best food, and catch sunrise at Mt. Haleakala – and I thought, what better person to embark on this jam-packed journey with me than the one who taught me everything I know? My mother took less than two seconds to agree and the planning began almost instantly.
Why traveling with your mom is always a good idea:
If you both live in different cities, states, or countries, this is a great opportunity to catch up.
You're now an adult, which means that parental filter your mom carried with her for so long will likely dissipate. You might learn a lot about her that you never knew!
She'll probably make the perfect travel buddy because odds are, you learned your travel habits from her or your father. No one can keep up with my crazy itineraries like her!
If things go wrong, you know she'll have your back no matter what.
And for the memories of course! There's nothing better than spending quality time in a cool and exciting place with the person who knows you best.
This post is in partnership with Maui Beachside. All opinions, photos, and writing are my own.
What to Pack (Carry-On):
Jean shorts (2 pair)
One nice outfit (I brought a romper)
Lava lava (sarong)
Tevas (for hiking and waterfalls)
DSLR + 24-70mm lens
Tripod - for creamy waterfall shots and sunrise at Haleakala
Puffy Coat (for Haleakala)
Beanie (for Haleakala)
Leggings (for Haleakala)
Little gloves if you have them (for Haleakala)
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We spent five nights in "paradise" staying at the beautiful two-bedroom Maui Beachside oceanfront condo – one of two Maui Beachside condos in Kihei.
Its decor is on point, taking inspiration from the island it calls home with a blue and white theme and island vibes. Maui Beachside 2 features two bathrooms, three beds (one bunk bed), a washer and dryer, a living and dining area, a full kitchen and a spacious lanai with everything you could possibly need, whether you're spending five nights or two weeks in this oceanside retreat. I'm talking beach chairs, coolers, shampoo and conditioner, Hulu, and more thoughtful amenities that made for a more than comfortable stay. Pool and hot tub access is also part of the deal where you'll find stand up paddleboards and snorkel gear; the beach is just a few steps away.
Every morning my mom and I would enjoy coffee out on the lanai, watching the waves and the occasional kite surfer with a little banana bread, lilikoi butter, and fresh fruit from the stand across the street.
Can't wait? Scroll to the end to find out how you can receive a special discount
when you book a stay with Maui Beachside.
We loved Kihei's local feel – cute (and affordable) boutique shops and some of the island's best restaurants can be found in the Kihei Kalama Village, which is where we spent almost every night.
Our Favorite Kihei Eats + Drinks
Three's Bar and Grill - Get the lilikoi martini and the mahi mahi fish and chips!
Paia Fish Market - Fresh, locally caught fish? Yes, please. I had the ono fish tacos, but your fish choice is up to you! Don't leave Maui without giving this place a taste.
Tiki Bar - Fun (and sweet) tiki-themed drinks to get you in the island spirit.
Kihei Cafe - From loco moco and homemade corned beef hash to banana sweet bread French toast, this place has it all. **Cash only!
Arrive + Pool/Beach Day
Road to Hana (Part 1)
Road to Hana (Part 2)
Arrive + Pool/Beach Day!
I touched down at 1 p.m. and had about seven hours to kill until my mom flew in from the Marshall Islands, so I stopped by the store to pick up a few necessities (like sunscreen - this one is reef-safe!), checked in, and ran to the beach. I couldn't wait to feel the sand between my toes and soak up the warm Maui rays. Today was all about some much-needed R+R before the adventures began. A few island-themed drinks at Tiki Bar accompanied by live music and we hit the sack – we had a big day on the horizon.
I woke up to the smell of coffee and the sun setting the mountain aglow in the distance. We snacked on fruit on the lanai (there's a fruit stand just across the street), lathered on the sunscreen, and hit the road. Next stop: The Kahekili Highway.
A cliff to the left and a wall of rock to the right, my mom's knuckles were white as she gripped onto the steering wheel at full attention while we drove the twists and turns of Maui's infamous one-lane, two-way roads.
Vastly different from the Road to Hana, the Kahekili Highway is dotted with pastures on a remote stretch of undeveloped coastline between Honokohai and Waihe'e. It's a gorgeous but narrow highway on west Maui's North Shore. Almost all of my research said "Don't do it!" or "Too dangerous!" but I promise you, it's worth the adrenaline. Ok, hold up, let me clarify something: if you're afraid of heights or aren't comfortable behind the wheel, you probably shouldn't attempt the Kahekili Highway for your and everyone else's sake. There are a ton of pullouts, but if you encounter a driver who freezes because of the steep cliff on one side and a rock face on the other, well, that's not fun for anyone involved.
Pro Tip – Drive this (and every other) highway clockwise so you're hugging the land rather than the cliff when you pass cars. There aren't many (if any) guardrails on this road. You'll save yourself and your passenger a couple of heart attacks!
You'll pass Honokohau Bay (famous for its prime snorkeling), the Nakalele Blowhole, and the Olivine Pools before the one-lane road even begins, so if you'd like to get a taste of the highway without doing the scary drive, you can always stop by these attractions and turn back. If you do decide to brave the drive, don't get spooked from that first stretch of the one-lane highway (if you're headed in a clockwise direction)! We learned from our friend at Julia's Banana Bread stand that that's the worst section of the entire drive (she hasn't done it in 17 years!) so, if you can get through that you can do the rest! Take a minute to explore the tiny village of Kahakuloa, seemingly untouched since its creation in the 1800s, and snap a photo of the historic church (founded in 1887). Then, pick up some banana bread, lilikoi butter, and free limes (if you're lucky) at Julia's before continuing on.
Pro Tip - Download your maps before you head out! Service is scarce and some of these attractions lack signs. Try Maps.Me if you need an offline map provider.
At the top of the hill just after Kahakuloa, stop in Karen Lei’s Gallery for locally made gifts from Maui artists. There's also a food truck, tables, and a killer view – it's an awesome spot to grab lunch (and the last place to grab lunch between here and Kahului).
The kind woman at Julia's Banana Bread (her name sadly escapes me) gave us an awesome recommendation for a local waterfall hike on the highway. There are no signs, she said, so just look for a few cars in a pull-out and you've found it.
Vague, I thought, but sure, let's go for it. And sure enough, there was only one pull out with about four cars on the entire stretch of road – a tiny, overgrown trail seemed to lead straight off the cliff. So, against our survival instincts, we descended through trees and sugarcane down the Makamakaole Trail until we reached pool one of three – the sun seeping through the leaves reflected beautifully off the water.
Further down, a second pool appeared. We followed the trail downriver until we reached the finale. A banyan tree marked the beginning of the falls and we climbed down its roots to its base. The falls had ivy on all sides and a smooth rocky area to the side, perfect for a quick beverage break before climbing back up and out.
So thankful for this recommendation! It was awesome. There were only two other people there, unlike the waterfalls you'll find on the Road to Hana. A local treasure for sure.
And, just like that, the highway was coming to an end and it was time to head back to our new home. We left the condo around 9 a.m. and finished the highway by about 3, so we had a little time to spare and we spent it at Big Beach back in Kihei where we watched kids tear up the big break with boogie boards on the beautiful cliff-flanked sandy beach. Definitely one of my favorite Maui beaches!
But don't stop there. Follow this same road all the way down to its terminus. You'll pass through stunning lava fields with a beautiful view of Haleakala in the background. It lit up beautifully during sunset.
Mt. Haleakala + Road to Hana
Our alarm goes off at 3 a.m. and the morning person that I'm not miraculously hopped out of bed with a smile because it was about to be an epic day. It's a 1.5-hour drive to the top of Mt. Haleakala, the world's largest dormant volcano, and catching sunrise over the crater is sort of a Maui rite of passage. Not going would be like traveling to France and not visiting the Eiffel Tower.
IMPORTANT Pro Tip - Permits are required to visit Mt. Haleakala at sunrise. They cost just $1 and go on sale three months in advance (they sell out fast). Visit this link to snag yourself a ticket.
The last stretch to the top is a series of switchbacks, but the good news is, it's a two-lane road and most of the traffic is headed in the same direction. Keep your eyes peeled for cows, though. They like to hang out by the side of the road and they can be a little startling in the dark.
Plan for a little traffic as you enter the park and make sure you arrive with at least 30 minutes to spare (or even earlier if you want some night shots - it's typically really clear up there!).
Pro Tip - Pack layers!! It may be hot and steamy down by the ocean, but it gets brisk when you're 10,000 feet high. I brought a beanie, a puffy down coat, and leggings and I was still a little chilled. The wind chill is what gets you – pack accordingly. Gloves would've been nice too.
You'll see everyone gathering at the ledge in the parking lot but venture up the marked trail for an even better view with a lot less people. You'd be surprised how few people want to walk the .5-mile round-trip trail to the highest point in the park. Highly recommend. The sun set the crater's red dirt aglow as it rose, and the rays fanned out in the sky above. It was spectacular!
Once the sun was up, we quickly drove to the actual summit (the road is closed while its dark) and took in the 360-degree views from the observation deck just as the clouds rolled in. But don't forget to look down! Little Chukar Partridges run around your feet among Haleakala Silverswords – the beautiful greenish-blue, shiny relative of the sunflower found only on Mt. Haleakala and the Big Island's volcanoes.
If you're feeling up to it (and have the time) consider hiking the volcano's trail network for some otherworldly scenery.
This postage stamp old-school plantation town in Maui's upcountry between Mt. Haleakala and Pa'ia is full of charm. I wish I could've spent more time here. We stopped in Cassanova for a morning latte and walked around the storefronts from a different time. Check out Driftwood for cute beach-themed gifts and pick up a flower headband called a "Haku" at Haku Maui.
Another one of Maui's sugarcane plantation towns, Pa'ia was founded in the late 19th century and today features a collection of shops, galleries, restaurants, and more. Hop out and snap a couple of pictures with the town's legendary surfboard fences, grab a bite to eat at the Paia Fish Market if you haven't done so at their Kihei location, maybe visit a couple of shops, and continue down the road to the first stop on the Road to Hana.
The Road to Hana
Ahhh the legendary Road to Hana in all its glory. Lush, green jungle, beautiful tropical plants, tons of stunning waterfalls, coves, bridges, fruit stands for days, and lots of Huli Huli chicken. Yes, what they say is true – there are roughly 620 turns and 59 bridges (most of which are one lane), so, let's start off with a Pro Tip, shall we?
Pro Tip - If you're into a little history and want to make sure you see at least the five must-visit Road to Hana attractions, download the Road to Hana, Maui Driving Tour app by GyPSy Guide. I never do audio guides, like ever, but this one proved to be pretty helpful, especially when Google maps isn't readily available with the lack of service over there. He automatically tracks your location and speaks up whenever you pass something of note. He also keeps you on a good time schedule if you're doing the Road in a day.
We alotted two days to explore this must-do Maui activity. Everyone I chatted with said one day is not enough, especially if you're trying to do it all (and you know I was). So, we rented camp gear from a guy in Hana and planned to spend the night by the ocean for two full days of ultimate exploration. Let's get started!
The first stop on the Road to Hana. You'll catch a glimpse of green sea turtles at this popular windsurf (and surf) spot so, make sure to get out and walk down the beach to the south end to see these cute sea creatures sunning themselves.
2. Twin Falls
There wasn't quite enough water, but it was beautiful nonetheless! The farmstand is super cute too. It's technically on private property but the owner is kind enough to let visitors walk the trail to the two different waterfalls. The guy on GyPSy Guide says it's not worth a stop if you're in a hurry, but I disagree! Check it out!
The Upper Waikani Falls (also known as the Three Bears Falls) was my absolute favorite!!!! You can see it from the road, but it's so much better up close. Park in one of the pullouts and walk back to the bridge where you'll see a trail on the side opposite the waterfall (not the side with the chain) and climb down – that's the worst part of the trail, I promise. Then it's a short walk to the falls. Make sure to jump in and swim around for a refreshing morning (can you believe it's still morning?!) dip.
These falls have a beautiful pool to the right of the bridge and cascade down a massive cliff to another pool below. Make sure to get out and check it out! You can't see the huge falls from inside the car. You'll pass many more waterfalls and streams as you drive your way down the winding road to Hana that you can explore at your leisure. I'm simply highlighting my favorites.
By this time, your stomach is probably starting to growl, and luckily, there's a marketplace in Nahiku serving some of the best food around. If you haven't had Huli Huli chicken yet, this is the place to snag a plate. But be careful – arrive too late and it might be sold out!
Look for the sign just before you reach Wainapanapa State Park and drive up the driveway to a cute little house that sells delicious chocolate made right there on the farm. If you have a cooler, this makes a great gift, if not, try a sample and buy a bar (or ten) for yourself to enjoy!
7. Camping at Wainapanapa
The black sand beach at Wainapanapa State Park is unreal and definitely worth a stop. The contrast of the bright green plants against the black lava is striking. Check out the blowhole and lava tube on-site.
It also happens to be one of only two campgrounds on the Road to Hana, so we picked up our gear from a guy just outside of Hana and set up camp under a tree in the grassy area just steps from the black sand beach.
If you're up for a little adventure, check out the freshwater pools just north of the black sand beach. Park in the parking lot and approach the fence – there's a sign that says, "falling rocks, proceed at your own risk." We walked around and just a few hundred feet or so, you'll approach the cave with water reflecting a deep blue hue. Look for toads! They're super cute.
9. Kaihalulu Beach (Red Sand Beach)
Easily my favorite beach on Maui, this hidden red sand beach isn't hard to find if you know what to look for. There are no signs, so I found the trail on Google Maps and figured it out that way. You'll want to park on Uakea Rd and walk to where it dead-ends at the gate. Then, walk through the Youth Center's grassy field towards the break in the bushes – that's the trail. It's just a short walk until it terminates at the beach! Easy as that. The red sand next to the blue water and under the towering red cliffs above is truly an amazing sight to see. Get there at sunrise or sunset for some long exposure shots if you can!
8. Hana Farms
Camping is all good and fun until it's dark at 6:30 p.m. and you don't want to sit in your tent for a couple hours while it downpours. Luckily, it was Friday, and Hana Farms had a live local Hawaiian band and delicious food just down the street. Everything they sell is locally sourced and tasty as all get out. The open-air structure is eye-catching in and of itself. There's a little shop on the street selling treats and the restaurant with additional seating is up top.
We ordered their Margherita pizza, a lilikoi (passionfruit) soda, and enjoyed the vibes. It's also BYOB, so if you have a bottle of wine or a six-pack, bring 'em! Everyone there was so kind and even offered up some great local sightseeing tips. It was an epic day to wind down for the evening and chat with a few locals.
Road to Hana (Continued)
After a beautiful morning watching sunrise on the black sand beach, we picked up a really freaking good breakfast burrito from The Surfing Burro food truck before packing up and embarking on the 45-minute drive to the Pipiwai trail, which covers the Ohe'o Pools, the bamboo forest, and Waimoku Falls. This 5-mile round-trip trail was my favorite activity of the entire five days!
The bamboo forest is simply magical but it's about a mile up the Pipiwai trail, so don't get discouraged! Once you get there, you're walking over boardwalk and rock under a canopy of bamboo leaves for at least a mile until it opens up to the impressive 400-foot Waimoku Falls. Flash floods are common, so if you do choose to approach the falls, do so with caution. We walked up to it to snap a couple photos and left. We live on the edge but we also know when to call it quits.
I'll say it again, DON'T MISS THIS HIKE! It's worth the extra 45-minute drive from Hana, trust me.
The Ohe'o Pools are back at the trailhead and they're a great way to cool off after your steamy hike through the jungle. Check to make sure there aren't any flash flood warnings and dive right in. Then, dry off on the tiny black sand beach where the river meets the sea.
10. Don't Stop There. Finish the Loop!
One of my favorite things about Maui is how quickly the landscape can change and how vastly different each part of the island is. The drive goes from lush jungle to grassy cliffs in a millisecond, and the second half of the loop past Hana was incredible. It pains me to think people turn around and drive back to Pa'ia 1) because the rest of the drive is so freaking beautiful in its own way and 2) because the Road to Hana is slow with a million twists and turns and lots to pay attention to. Once is enough.
The road is mostly two-laned with the exception of the beginning, but it does have loose gravel in some places. A 4WD car is a good idea, but I also saw a couple of Prius' braving the journey.
Stop at Kaupo General Store for a quick snack and/or souvenir – a starfruit tree grows in the parking lot – and don't be afraid to stop at the many pullouts along the way to snap a photo or simply take in the epic views. The beautiful cliffside church on your left just past the store is a must. Hop out and check it out – turn around for a beautiful view of Mt. Haleakala in the distance and keep an eye out for cute stray cats.
The rest of the road takes you through ancient lava fields and across canyons in Maui's most remote stretch of land. You'll see quite a few goats but other than that, it's pretty barren and beautiful.
You'll find MauiWine just as Pilani Highway turns into Kula Highway as you round the south end of the island, and it's a must for any white or red wine-lovers out there – just make sure you're there before 5. The tasting room occupies the guesthouse of the last reigning king of Hawaii, King Kalakaua. The Old Jail building (with walls of lava rock) on the land formerly known as the Rose Ranch was originally the office of a whaling captain and later housed criminals in its basement during the plantation period. The entire estate is overflowing with interesting history to drink in with your wine.
We tasted both flights, but the Pineapple Flight is definitely the way to go. Their pineapple wine is to die for, and if we weren't traveling with only carry-ons, I would've brought home a case. Take a self-guided tour around the property and take a gander at their vineyards as you continue down the highway. This place is on my must-list for any Maui visitor doing the Road to Hana or not.
We ended our Road to Hana epic at Three's Bar and Grill back in Kihei with a tasty lilikoi martini, mahi-mahi fish and chips, and papaya salad sushi. Yummmm.
Surfing + Lahaina
There are so many surfable beaches and coves on Maui but that doesn't mean their conditions are always at their prime. Check the Maui Surf Report for what's good and where to go so you know what you're getting yourself into. I picked up a board, booties, wax, and a rash guard from Surf Shack Maui for $30 a day and paddled out at Ukumehame Beach Park just before Lahaina. Careful: the coral is shallow!
Lahaina is Maui's biggest town and sees about two million people, garnering about 80 percent of Maui's tourism every year. It was the capital of the Kingdom fo Hawaii from 1820 to 1845. The main street buddies up to the water and still features a lot of its original buildings. Galleries, restaurants, shops, and more offer plenty to do for the meanderers, but the Pioneer Inn is the true eye candy here. Now a Best Western, the Pioneer Inn was originally built in 1901 when whaling and plantations were the big money-makers. It's been renovated of course, but they did their best to preserve this historic hotel's charm. Walk the streets, try some shaved ice (with the ice cream, of course), stop in the Golden Pineapple store, and take it all in, but then head back to Maui Beachside because it's a lot of tourism in one place.
Oh, wait! Definitely hit up Aloha Mixed Plate before you leave. I had the best mochiko chicken of my life here AND, if you're lucky, you'll get a seat just a few feet away from the lapping waves of the Pacific.
Pro tip - Margaritas and Mai Tai's are only $4 during happy hour ;)
Whew! You made it. All that's left is dropping my dear mother off at the airport and spending the evening relaxing on Maui Beachside's lanai with a guava juice and the last of our banana bread. But I couldn't leave this beautiful island without tasting its favorite breakfast joint, Kihei Caffe.
Pro Tip - Wait out the line and stop in at about 11 a.m. Then, enjoy everything from sweet bread french toast with Maui bananas to loco moco and corned beef hash.
How to Book
Huge thank you to Maui Beachside for hosting me these six incredible days!
Looking for something a little smaller? Stacey has a second adorable property just a few minutes south called Maui Beachside 1. Check it out here.