An Adventure-Packed 5-Day Maui ItineraryMaybe it’s the 80+ multi-colored beaches, the 10,000-foot summit of Haleakalā, or the dense green rainforest near Hāna. If you’re planning a Maui adventure and wondering what to do, read on for my 5-day Maui itinerary. Here, I break down my favorite way to spend five days in Maui.🧉🌴AuthorsRachelOffDuty
DestinationsMauiItinerary

DAY ONE: Lahaina & Ka’anapali 🏝️

Leoda's Kitchen and Pie Shop
On your way to the beach, stop at Leoda’s Pie Shop in Olowalu for a bacon and egg sandwich to fuel up for your first day. Just down the road, you’ll also find a small food truck area with some tasty breakfast bites. Baya Bowls and TaquerEATa are my personal favorites.
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Olowalu Beach
West Maui is home to several beautiful beaches lined up in quick succession, starting in Olowalu. You won’t have a hard time finding one to enjoy!
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Kaanapali Beach
Pick one or two beaches and spend your day snorkeling, sunbathing, or swimming before heading back to Lahaina for dinner. Other great options include Kahekili Beach Park, Honokowai Beach Park, Oneloa Beach, DT Fleming Beach Park, and Slaughterhouse Beach.
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Honoapiilani Food Truck Park
If you just can’t bring yourself to leave, grab dinner near the beach here.
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The Plantation House
A little further up the road, but this is an amazing dinner spot if you're up for a little bit of a drive.
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DAY TWO: Haleakala NP & Upcountry Maui 🌋

Haleakalā Summit
Day two of your Maui adventures starts with a super early wake-up call. You’re going to catch one of the most staggeringly beautiful sunrises at the top of the world today!
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Private Haleakala Summit & Stroll from Kahului
Meaning “House of the Sun,” Haleakalā has been a place of cultural and spiritual significance for Hawaiians for centuries. If you go for sunrise, you may even hear locals lead daily ritual chanting to greet the sun. You are encouraged to participate!
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Halemau'u Trail
Looking for something longer? The Halemauʻu Trail covers 10 miles across Haleakalā National Park on Maui to the Haleakalā Crater, which is 2,600 feet deep.
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Leleiwi Overlook Trail
While in the Summit District of the national park, be sure to explore some Haleakalā hiking trails, like the short Leleiwi Overlook.
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Kula Bistro
After your morning in Haleakalā (or before you go for sunset), grab a bite in upcountry Maui at Kula Bistro and wander around the paniolo (Hawaiian cowboy) town of Makawao.
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Hosmer Grove Campground
Try to cinch a campsite at Hosmer Grove Campground, just 20–30 minutes from the summit. You’ll want to make reservations several months in advance, as there are only six campsites. But if you can find an open spot, you’ll be rewarded with incredible stargazing by night and easy access to an unforgettable sunrise.
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Sherri Reeve Gallery & Gifts
This beautiful art gallery in downtown Makawao is a great spot to stop and grab a souvenir.
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DAY THREE: Water Activities & ‘Iao Valley 🎋

Ukumehame Beach Park
Since you spent yesterday exploring the highest summit in Maui, start day three of your 5-day Maui itinerary at sea level by getting out on the water! Take a surfing lesson at Ukumehame Beach Park.
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Semi Private Surf Lessons with Experienced Coaches
Take a private lesson with Maui Surf Girls! This woman-owned surf school is the best on the island. You’ll be standing up before the end of the two-hour class! If I can, so can you!
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5 Hour Molokini Snorkel & Turtle Tour in Maui
Maui is home to some astounding underwater ecosystems. Two impressive Maui snorkeling sites are Coral Gardens and Molokini Crater, both accessible only by boat with tours like this.
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From Maalaea: Whale Watching Tour Aboard the Quicksilver
Whale watching season in the Hawaiian Islands typically peaks from December to February. See whales on Maui with a kayaking tour or a 2-hour catamaran tour, where there’s a good chance you’ll spot dolphins or sea turtles too.
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ʻĪao Valley State Monument
If you have less time, visit the ‘Iao Needle State Monument, which takes just 10 minutes to reach via a well-marked pedestrian trail. This ‘needle’ (more like a pointy hill) served as a lookout point during the battle that was ultimately a turning point in Hawaiian history.
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Waihee Ridge Trail
If you have more time, I also recommend spending around 2–3 hours hiking the Waiheʻe Ridge Trail. This 4-mile trail will wear you out, but you’ll quickly be rewarded with a waterfall and 360-degree views of the West Maui Forest Reserve and the Pacific Ocean. Depending on the weather and time of day, you’ll either have clear views at the top or find yourself walking among the clouds!
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DAY FOUR: Pa’ia and the Road to Hana 🌊

ʻOheʻo Gulch
Once inside Haleakalā National Park, the gulch offers stunning views of the ocean, waterfalls, and the Seven Sacred Pools!
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Pipiwai Trail
Take the 4-mile out-and-back Pipiwai Trail, where you’ll find Waimoku Falls.
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Waimoku Falls
Not only does it have an amazing waterfall, but the trail also hosts an exquisite bamboo forest.
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Paia Bay Coffee & Bar
You could easily spend a whole day in Pa’ia. But to fit it into your 5-day Maui itinerary, plan to stop at Pa’ia either before your road trip (for breakfast) or after (for dinner and drinks). Pa‘ia Bay is a great spot before getting on the road.
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Cafe Mambo
By now, you've worked up an appetite. Check out Cafe Mambo and sample yummy dishes like crispy duck fajitas, smash burgers, and creative brunch options.
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Paia Fish Market Restaurant
Pa‘ia Fish Market stands out for its ultra-fresh, locally caught fish, generous portions, affordable prices, and laid-back communal atmosphere with a classic Hawaiian surf vibe.
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nyloS Restaurant
The restaurant is operated by chefs Jeremy Solyn and Paulina Solyn, who have created a unique, chef-driven experience that consistently ranks among Hawaii’s top dining destinations.
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Mama's Fish House
Dinner Option #2: Note that this place gets packed, and advance reservations are strongly recommended.
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DAY FIVE: Wailea, Kihei, and South Shore Maui 🌞

The Shops at Wailea
The Shops at Wailea are where you’ll find the best selection of designer names and high-end boutiques on the island.
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Makena Beach
Makena Beach (Big Beach) is picturesque and perfect for laying out, but the shorebreak is known to be pretty intense.
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Little Beach
Little Beach is unofficially a ‘clothes-optional’ beach tucked away next to Big Beach. Other good beach options are Wailea Beach, Po’olenalena Beach, and One‘uli Beach.
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Maui Brewing Co.
When you’ve had your fill of surf, sea, and sun, finish your day with a stop at Maui Brewing Company in Kihei. What started as a single brewpub in 2005 has now made a name for itself on a national scale. You might’ve even seen Maui Brewing cans at grocery stores where you live! Go visit the brewery and enjoy a pint (or a flight), plus food, at their on-site beer garden, which boasts 36 craft and specialty beers on tap.
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Stay Options 🏡

Paia Inn Hotel
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Bamboo Valley Inn
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Hana-Maui Resort, a Destination by Hyatt Hotel
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Hana Kai Maui
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