From the surfer town of Pā’ia, along the winding curves of the Road to Hāna, and down the rugged cliffs of Kahekili Highway, buckle up for some adventures along winding highways on Maui’s Windward coast!
Written by Lauren
This post contains affiliate links.
Maybe it was visions of all-inclusive resorts with bottomless Mai Tai’s and idyllic white sand beaches beneath swaying palm trees that first beckoned you to book your trip to Maui.
(No judgement. Same, same.)
You’re here for the sunshine and aloha vibes. I got you.
But have you ever found yourself wondering if there might be something more?
(No? Then, carry on, my friend.)
But perhaps you’re also starting to feel the call to explore beyond the resort to experience a more multi-faceted Maui?
If that’s you, then you’re in the right place!
From the laid-back north shore surfer town of Pā’ia, through the lush, tropical paradise along the Road to Hāna, and down the rugged cliffs and razor blade switchbacks of the Kahekili Highway, there is so much to explore on this side of the island.
In each section of the itinerary, we’ll dig into the details of the three different areas, including the highlights, weather, and driving distances to other locations on the island. Then we’ll break down what we did and how we did it, with tips on how you can have an even better trip!
We also provide some recommendations on where to stay for your 3 days on Maui’s windward coast.
Jump right to it …
Itinerary overview
Itinerary
Day 1 | North shore + Pā’ia
Highlights and things to do in Pā’ia
Pā’ia weather
Driving distances from Pā’ia
Pā’ia Pocket Guide
Day 2 | Road to Hāna
Road to Hāna Pocket Guide
Day 3 | Drive the Kahekili Highway
Central Maui
Central Maui weather
Driving distances from Kahului
Driving the Kahekili Highway
Kahekili Highway Pocket Guide
Map
Accommodations
Reading Recommendations
Itinerary Overview
Vibe: road trip, scenic drives, stunning views, small town explorations, hikes, waterfalls
3 Day Maui Windward Coast Itinerary
On the itinerary:
Day 1 | Pā’ia + the north shore
Day 2 | Road to Hāna
Day 3 | Explore Central Maui + drive the Kahekili Highway
Day 1 | Pā’ia + the north shore
On the itinerary:
➳ Beach
➳ Check into accommodations
➳ Explore Pā’ia
Pā’ia
Pā’ia is a quaint surfer town on the north shore full of character, charm, and hippies (don’t be surprised if you see most locals going barefoot in these parts). In some ways, Pā’ia feels like it stands still in time, but it’s full of cute shops, good eats, hidden gems, and all the chill vibes.
Parking: Paia Town Public Parking
Things to do in Pā’ia
◦ Ho’okipa Beach Park
◦ Paia Fish Market
◦ Lilikoi Paia Maui
◦ Lele by Adelina
◦ Paia Bay Coffee Bar
◦ Belle Surf Cafe
◦ Vana Paia
◦ Milagros Food Co
Waves and weather in Pā’ia
◦ Hot and humid
◦ Mostly sunny with 250 days of sunshine a year
◦ Winter rainstorms are common
In the winter months, you’re looking at highs in the 80s (°F) during the day, and dropping to lows of 60s (°F) during the night.
In summer, Pā’ia averages mid to high 80s (°F) during the day and dropping to the high 60s (°F) and low 70s (°F) at night.
Because the north shore is on the windward side of the island, it gets hit with big waves in winter. So, it’s great if you’re a surfer. Not so great if you’re a casual swimmer.
I caution even good swimmers from getting in the north shore waters during the winter. Stick to the calmer waters of South Maui in Kīhei and Kāʻanapali.
Distances from Pā’ia
Distance from Kahului airport: 20 minutes
Distance to Makawao: 15 minutes
Distance to Hāna: 1 hour 45 minutes
Distance to Kapalua: 1 hour
Distance to Lāhainā: 50 minutes
Distance to Haleakalā: 50 minutes
Distance to Kīhei: 30 minutes
Distance to Wailea: 35 minutes
➳ Beach
I started off my fifth day on the island by saying goodbye to Heather, loading my bags into the Jeep, and heading off to Olowalu Beach in West Maui.
◦ Papalaua Wayside Park Beach (Leeward side)
◦ Ho’okipa Beach Park in Pā’ia (not for swimming in winter / experienced surfers + windsurfers only)
Papalaua Wayside Park Beach
22 Honoapiilani Highway, Wailuku
It’s hard to miss this long stretch of beach as you pass by on the scenic Honoapiilani Highway. I knew it was a spot I had to check out because of the ability to pull right up to the beach and have access to shade underneath the trees.
After making a slow pass-by to get a lay of the land, I pulled over to my spot, did a quick three-point turn, and backed the Jeep up in between the trees. And there I was—with my own little slice of beach paradise all to myself. Just me, the sun, the sea, the sand, and the sand crabs.
I whiled away a few hours swimming in the shallow, clear waters, laying out in the sun, and just enjoying my little slice of paradise (and pretending like I was a local for a short while).
Heads up
Because you can camp at these beaches, you will see a lot of, shall we say, permanent residents who have set up shop here under the makeshift shelter of vans, tents, canopies, and tarps. Some even had outdoor kitchen setups. Whether by choice or circumstance, homelessness is a thing, even in paradise (especially in paradise. Have you seen those rent rates?).
It’s not a tent city by any stretch, but the presence of long-term campers might not be your vibe.
All that being said, I was actually parked next to some windblown and weathered lifers and didn’t have any issues. I didn’t bother them and they didn’t bother me, nor did I feel unsafe at any time.
All in all, it’s an ideal spot to layout in the sun, swim in the clear shallow water, and put the snorkel gear on and explore the labyrinthine network between the underwater rocky reefs. Or hang up a hammock between the trees.
Ho’okipa Beach Park
Alternatively, if you’d rather head straight to Pā’ia (or you’re already there), spend the morning at Ho’okipa Beach Park.
Though, note, this is not a place to swim in winter.
But it is great for catching waves and windsurfing—or watching from the shore!
In fact, it is a legendary windsurfing locale (experts only).
➳ Check in to your accommodations
See some of our recommendations for places to stay below.
We recommend Pā’ia for your base of operations for these three days of Windward exploring since it is centrally located along the coast, and also because it’s a really cute little town to explore, get good eats, and catch that north shore surfer vibe.
➳ Explore Pā’ia
◦ Eat at Paia Fish Market
◦ Shop for souvenirs in Lilikoi Paia Maui and Lele by Adelina on Baldwin Avenue
◦ Drinks and snacks at Paia Bay Coffee Bar (now Belle Surf Cafe)
◦ Nightcap at Vana Paia
After checking in to our room and getting settled, my friend (and ever-ready travel buddy) Ashley and I decided to hit the town for the afternoon.
If you’re not staying in walking distance of downtown Pā’ia, snag a free parking spot in the Paia Town Public Parking lot. It’s a bit of a tight squeeze in there and can sometimes require some MacGyver maneuvers to navigate, but I did it with a four door Jeep Wrangler—so it is possible!
Pā’ia was such an unexpected gem!
Made all the better by the fact that I had not planned for it, and we just kind of stumbled upon it (like all the best things on an adventure, am I right?)
We ate a late lunch at Paia Fish Market. Leisurely strolled past the shops in town and browsed for souvenirs in Lilikoi Paia Maui and Lele by Adelina on Baldwin Avenue.
Then, in the spirit of adventure, we (quite literally) stumbled upon Paia Bay Coffee Bar.
*They’ve since moved locations, but the space is now home to another one of our favorites: Belle Surf Cafe!
We had popped into a women’s boutique store to peruse the bikinis and crop tops (because it might have taken us until our thirties to embrace the whole exposed midriff thing, but goddamnit we finally made it), and then, from the back of the store, we heard it: the strumming of live music and the tell-tale clink of glasses and cafe chitchat.
What could that be? We wondered. Like a tropical version of the wardrobe to Narnia, we made our way through the throngs of colorful swimsuits to the back of the store and went through the back doorway to find . . . an oasis, a tropical paradise hidden amongst the brick and mortar stores.
Another one of those happy happenstance moments.
We took a seat at one of the tables underneath the breezy cloth canopy, string lights, fans, and hanging plants. We ordered drinks of the adult kind from the friendly and accommodating bartender, and spent a lovely hour or two shooting the breeze there, catching up and listening to the local troubadour from the small stage front and center.
You know what’s better than a place that serves coffee? A place that serves coffee and alcohol. And better yet, a place that serves coffee and alcohol and has live music. Oh yeah, and they have food.
(Alternative milk options include: oat, macadamia, coconut, and usually almond.)
Speaking of embracing exposed midriffs, Ashely got the cropped muscle tank from the merch section. I still regret not getting one.
I loved this place so much, I went back several times.
We ended the night with drinks at Vana Paia.
A long, narrow hallway lit by the soft glow of seashell chandeliers leads you out into a courtyard under a sprawling tree canopy.
With the string lights above us and the dancing flames of the fire next to us, it felt like we were transported worlds away. When the dark skies opened up and began to pour, guests sought cover under opened umbrellas, watching as staff hand-cranked the awnings open to close the gaps above. And then, all went on as it had been. Seats were taken, drinks were drunk, and conversations continued as the soft patter of rain fell down around us.
After drinks, we stopped by the Shell station next to the parking lot before heading back to our room to stock up on gas and fill the cooler with ice and water bottles.
Pā’ia
Eats + Drinks
Belle Surf Cafe
Paia Bay Coffee Bar
Paia Fish Market
Milagros Food Co
Vana Paia
Beach
Ho’okipa Beach Park
Shop
Lilikoi Paia Maui
Lele by Adelina
Day 2 | East Maui + the Road to Hāna
On the itinerary:
➳ Stop in Pā’ia for breakfast, snacks, and gas
➳ Swim in the Twin Falls waterfalls
➳ Huelo Lookout Stand for coffee and snacks
➳ Hike the Waikamoi Nature Trail
➳ Explore scenic overlook on the Ke’anae Peninsula
➳ Stop at Pua’a Ka’a State Wayside Park for a tailgate picnic lunch
➳ Coconut Glen’s for dairy-free ice cream
➳ Shop Hana Gold Chocolate Farm roadside stand
➳ Explore Wai’anapanapa State Park’s black sand beach, lava tunnels, and trails
➳ Hāna
The Road to Hāna is a very popular tourist attraction in Maui. An average of 2,000 cars a day ride this road. So, just know that ahead of time.
All in all, the Road to Hāna would take you roughly two hours to drive the 64 miles, one way, without stopping.
But, of course, the whole point of the drive is to stop and take in the scenery! The drive is the destination.
Along the winding (sometimes rugged, definitely remote) drive, you’ll find waterfalls aplenty, trails and gardens to stretch your legs, and some roadside food stands—with coffee, shave ice, ice cream (even dairy free!), banana bread, açaí bowls, and local grinds. In Hāna, you’ll have more culinary choices.
Road to Hāna
Stop in Pā’ia for breakfast, snacks, and gas
Twin Falls
Huelo Lookout Stand
Waikamoi Nature Trail
Ke’anae Peninsula 🚻
Pua’a Ka’a State Wayside Park 🚻
Coconut Glen’s
Hana Gold Chocolate Farm
Wai’anapanapa State Park 🚻
Hāna
Day 3 | Central Maui + the Kahekili Highway
On the itinerary:
➳ Kahului in Central Maui
➳ Explore stops along Kahekili Highway
Central Maui
Home to Wailuku, Kahului, the Central Valley, and the Kahekili Highway. It is a place many visitors pass through, but don’t stay.
Wailuku is the seat of government on Maui. So here’s where you’ll find many government buildings.
Kahului is the cradle of civilization on Maui. Here you’ll find: the airport, Whole Foods, Costco, malls, and the movie theatre.
The Central Valley is where 37,000 acres of former sugar plantation once resided. It is still in use today for agriculture. This is also the part you will drive through quite a bit on either the Honopiilani Highway (30) or Kuihelani Highway (380) to cross the island.
The majority of this side of the island is composed of the West Maui Mountains and the West Maui volcano, Mauna Kahālāwai, the “holding house of water”. Most of this land is in the West Maui Forest Reserve and West Maui Natural Area Reserve.
On the windward side of the western volcano, along the Kahekili Highway, you will find plenty of hikes alongside mountain streams, art galleries to peruse, and scenic lookouts.
Things to do in Central Maui:
◦ Eat at Kahului Food Truck Park
◦ Shop
◦ ʻĪao Valley + ʻĪao Needle
◦ Kepaniwai Heritage Gardens
◦ Dine at Cafe O’Lei at the Plantation House
Weather in Central Maui
Kahului is very dry and windy. It tends to be partly cloudy, with the winter months being the clearest.
Highs in the high 80s (°F) and lows of 70s (°F) in the summer.
Highs of 80 (°F) and lows of mid-60s (°F) in the winter months.
Driving distances from Kahului
Distance from Kahului airport: 10 minutes
Distance to Makawao: 25 minutes
Distance to Pā’ia: 20 minutes
Distance to Hāna: 2 hours
Distance to Kapalua: 1+ hour
Distance to Lāhainā: 40 minutes
Distance to Kāʻanapali: 45 minutes
Distance to Haleakalā: 52 minutes
Distance to Kīhei: 30 minutes
Distance to Wailea: 35 minutes
➳ Kahului
Eat at Kahului Food Truck Park
Shop
◦ Mom and Pop shops on Market Street in Wailuku
◦ Whole Foods and Costco
◦ Maui Friends of the Library bookstore at Queen Ka’ahumanu Center
ʻĪao Valley + ʻĪao Needle
Pronounced eee – ow, this is the sacred resting place of Maui’s chief’s. It’s also the site of Maui’s last stand, and the subsequent massacre of its troops, against Kamehameha’s campaign for island unification.
◦ Parking: $10 per car + $5 per person
◦ Mostly paved trails
◦ 134 steps to the lookout over the lush valley
There’s also a stream here you can dip your feet (or your entire body) in if the conditions are safe. This is discouraged, but permitted.
Kepaniwai Heritage Gardens
Honors the different ethnic groups who have settled in Maui
Take a guided tour through the rainforest to waterfalls
Cafe O’Lei at the Plantation House for lunch
A scenic dining experience in the valley
➳ Drive the Kahekili Highway
Things to do along Kahekili Highway:
◦ Hike the Honolua Bay walking trail
◦ Take in the scenic views at Honokohau Lookout
◦ See the Nakalele Blowhole
◦ Hike the Oahi Trail
◦ Swim the natural pools at Olivine Pools Trail
◦ Explore Kahakuloa Village
◦ Kahakuloa Head
◦ Stroll the grounds at Turnbull Studios + Sculpture Garden
◦ Hike Makamakaole Trail / 13 crossings or the Waihee Ridge Trail
◦ Dinner at Mama’s Fish House
Like the Road to Hāna except without all the lush, jungle vibes and ten times more treacherous. Fun!
Though Kahekili Highway is more exposed (think rugged with coastal cliffs), the views are just as stunning. Maybe even more so for the stark contrast of deep azure waters against the jagged lava rock cliffs.
I never felt like I was going to drive off the side of a cliff unexpectedly along the Road to Hāna.
I definitely did here.
Ever have to backup a Jeep Wrangler, with no rearview camera, on a tight one-way curving road, with little to no guardrail keeping you from plummeting to certain death down a cliffside, to let another car pass you by? Talk about a nerve-wracking, heart-pumping scary situation! (I also never had to backup on the Road to Hāna.)
That is the Kahekili Highway, my friends.
(Take a quick minute here to scroll down to the map below and zoom in on the Kahekili part—go on, I’ll wait. See all those zigs? All those zags? I wouldn’t say don’t do it, I just want you to know what you’re getting into.)
That being said, do I feel the need to do it again? Nope, not even a little bit.
Okay, maybe a little bit.
But let us continue our journey.
Besides for the adventure of the drive itself, there is plenty to explore along the way: hikes, art galleries, and lookouts, oh my!
Named after Kahekili, the last king of Maui, who put up a real fight against Kamehameha, who was hell-bent on conquering all of the Hawaiian islands. Kahekili was one bad-looking mama jama. And by bad, I mean fierce. Dude had tattoos darkening one side of his entire body, head to toe. And legend has it he also loved a good cliff dive, or lele kawa. Not even Captain Cook was willing to f*ck around with this guy. Ready for this crazy Star Wars-esqe twist? Kamehameha eventually defeated Kahekili only to find out years later that Kahekili WAS HIS FATHER!
Damn, that’s some Darth Vader shit.
Who knew it all began on a little island in the Pacific?
What you need to know driving the Kahekili Highway
The 27 mile drive from Kahului to Kapalua will take you roughly an hour and fifteen minutes without stopping.
From Kahului, turn right onto Kahului Beach Road (3400). Stay to the right on Kahului Beach Road until you have to make a hard right onto Kahekili Highway (340).
When I did this drive, I did it from east (Kahului) to west (Kapalua). However, our beloved friends and guides at Maui Revealed recommend doing the drive from west (Kapalua) to east (Kahului). This way, you’ll be driving on the inland part of the road, as opposed to cliffside (makes sense). They also say the views are better from this route.
That being said here are your options:
Option 1: Head to Kapalua via the valley and West Maui, then head back to Kahului in a clockwise direction
Option 2: Drive the Kahekili Highway in entirety from east to west, stop in Kapalua, and then take a more leisurely approach to driving Kahekili Highway on the way back towards Kahului
Should you come grill to grill with another car (and there’s no shoulder or turnout), the driver heading downhill is the one who needs to backup and make way for the other car, because it’s easier to maintain control going uphill rather than downhill.
Watch for cows and horses trying to hitch a ride!
As always, don’t forget your Shaka Guide to the West Maui Coastline!
Shaka Guide: History, legends, stories
I’d be completely remiss if I didn’t tell you all about
Shaka Guide’s West Maui Coastline audio tour.
This audio tour is the perfect companion while driving the West Maui coastline. Just download the tour in the app and hit start when you’re ready to hit the road.
The app connects to your GPS and will guide you along the road, where you’ll learn about the interesting Hawaiian history and legends of places along the way, as well as the best places to stop!
It’s like having an insider right in the car with you, without, you know, actually having to have a stranger in your car and having to make small talk.
You can play your music between audio points, and when you’re nearing your next destination, the audio tour will come back on. Easy, breezy, just the way we like our road trips to be.
You’ll hear some bewildering stories of Hawaii’s history, as well as some that are, quite frankly, very dire. But all in all, we loved learning about Hawaiian history and all about King Kamehameha. Also, the narrators laugh is a 10/10 dad laugh and we are here for it!
Coming from west to east
Honolua Bay walking trail
Around 1 mile total, this dirt trail will lead you under the lush canopy of a seaside forest out to a sweeping view of the Big Blue at Honolua Bay.
The trail is rated as moderate, as it does get steep and narrow towards the cliffs, and can be muddy (read: slippery) after a rainfall.
Honokohau Lookout
Shoulder pull-over for scenic views
Nakalele Blowhole
Most spectacular spectacle at high tide and high surf
Though, unfortunately for me, I could not figure out where the trail leading down to it was, and quickly ended up in the wrong place fast (as in, scaling the side of a cliff like a mountain goat). I’m going to chalk this one up to traveler’s fatigue because, as you can see from all the Jeep’s in the video below, there were plenty of other people there who managed to figure it out.
A few notes:
◦ Use common sense — you’re next to the ocean. Anything can happen.
◦ Don’t get too close to the blowhole
◦ Don’t turn your back on the ocean
◦ Don’t take rocks from Hawaii, as to not incur the volcano goddess Pele’s wrath (but seriously though)
Oahi Trail
1.2 miles round trip
There is a parking lot at the trailhead
Make sure to go to the right — counterclockwise — for the best experience
Olivine Pools Trail
Natural swimming pools carved out of the lava rocks! It’s like swimming in the ocean, without swimming in the ocean.
As always, use discretion. Moana be a tempestuous mistress.
Kahakuloa Village
Visit some food stands and Karen Lei’s gallery
Kahakuloa Head
Lookout for the Tall Lord, a prominent land formation on the coast
Stroll the grounds at Turnbull Studios + Sculpture Garden
A nice place to stop and stretch your legs (and perhaps, calm your nerves) is at Steve and Christine Turnbull’s art gallery, where you can walk the two acre sculpture garden, featuring the work of Maui’s finest artists.
Check website for hours
I will definitely be checking this out next time I’m in town!
Makamakaole Trail / 13 crossings
So called because you have to cross the Makamaka’ole Stream 13 times. Your reward? The Makamaka’ole Falls where you can take a dip in the falls pool.
Rated beginner to intermediate
Two miles
1 – 2 hours
Waihee Ridge Trail
A steep climb up a mountain ridge—hot, hard, but with great views of the northern Windward coast.
Where to park:
Waihee Ridge Trailhead parking lot
Turn left off Kahekili Highway onto Maluhia Road, across the street from Mendes Ranch Maui, and drive up until you reach the parking lot.
4 miles out and back
3 hours (if you make it to the top—we didn’t)
Hard (1600ft elevation gain)
Port-a-potty at trailhead parking lot
Dogs allowed, but must be leashed
Since this trek is very exposed, we recommend doing it in the morning or late afternoon. Bring plenty of water and don’t forget to wear a hat and sunscreen.
This hike begins in a dusty parking lot off the winding Kahekili Highway and starts with a steep incline up a paved drive. From there, you enter a small forested stretch of mostly gentle switchbacks. Enjoy the shade while you can!
After you exit the tree line, the narrow, vegetation-lined trail continues its switch backs up the very-exposed ridge.
Along this stretch, you’ll have views looking down into the carved, tree-carpeted valley below on one side, and the Big Blue on the other.
For all our huffing and puffing, we did not make it all the way to the top.
The way back is mercifully downhill.
If you’re lucky, a friendly equine will happily welcome you back from the pasture adjacent to the parking lot (with only minimal side-eye).
Dinner at Mama’s Fish House
Celebrate your survival — err, I mean success — at completing the Kahekili Highway at one of the most scenic dining locales on the entire restaurant.
Make sure you make reservations! (They book months in advance)
You might want to give yourself time to go back to your base of operations to clean yourself up a bit before heading to dinner, Mama’s Fish House gives major date night vibes.
Kahekili Highway
Honolua Bay Walking Trail
Honokohau Lookout
Nakalele Blowhole
Oahi Trail
Olivine Pools Trail
Kahakuloa Village
Kahakuloa Head
Turnbull Studios + Sculpture Garden
Makamakaole Trail/13 Crossings Trail
Waihee Ridge Trail
Mama’s Fish House
X marks the spot
Accommodations
Here are three stays we recommend to have the easiest access to exploring Maui’s Windward coast.
Pā’ia
Stay right in the heart of Pā’ia in this sweet boutique surf hotel with tapas and cocktail restaurant Vana Paia on site!
Expedia
Expedia
Expedia
Expedia
Expedia
Expedia
Makawao
Retreat to 5.6 acres overlooking the north shore and central valley featuring a swimming pool, meditation labyrinth, wellness spa, on-site farm to table restaurant, outdoor fire pits, gathering spaces, yoga studios, and a hammock forest to rest and restore between all your adventuring!
Expedia
Expedia
Expedia
Expedia
Expedia
Expedia
Makawao
Relaxing, romantic getaway with gorgeous views!
Expedia
Expedia
Expedia
Reading recommendations
Maui Revealed
This is my go-to resource for Maui and I cannot recommend this book enough!
Andrew is the real deal. He (and now his team) live and breathe Hawaii in a way that seriously makes me jealous, spending two years on the ground researching, exploring, and doing all the things before publishing their blue guidebooks.
All written with a dash of humor and a smattering of sarcasm, it’s the perfect companion for your Maui trip planning.
In Maui Revealed, he covers:
- Maui’s history
- Everything you need to know about Maui
- All 6 areas of the island, plus 3 offshore islands
- Reviews of all beaches
- Activities
- Adventures
- Dining
And here you thought Maui was all beaches and Mai Tai’s!
So, if you hear your adventurous side calling, get out on the road and discover some of the many things Maui’s windward coast—like surfer towns, roadside waterfalls, black sand beaches, and scenic roads with hikes and locally owned businesses along the way—has to offer!
Mahalo!
The Maui Collection
About Lauren
Reader, writer, traveller, itinerary-creator & mapmaker extraordinaire
Detroit-born, Nashville-bent, everywhere-bound, some of her favorite things include drinking coffee, eating in roadside diners frequented by locals and truckers alike, reading entire guidebooks front to back, visiting local bookshops, spirit questing in New Mexico, watching wildlife documentaries, listening to unapologetic amounts of Taylor Swift, and sitting in aisle seats. To name a few.
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