5 Day Maui Itinerary: How to Experience the Best of Maui

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When it comes to the sparkling waters and laidback nature of Hawaii, even a full week seems hardly enough to take it all in.

Between the awe-inspiring Mount Haleakala, fabled Garden of Eden and sandy swatches like Ka’anapali Beach, Maui presents a characterful getaway fit for solo travelers and families.

Not to mention, the sugarcane and pineapple plantations, botanical parks and dynamic coastline. The list goes on.

Behind the natural attractions lay rich history and culture as well. Travelers can dip into traditional museums or absorb via performance arts – the Hawaiian Luau is a fine dine-and-watch combo.

In this 5 day Maui itinerary, experience the “real Hawaii” in high definition.

If you’d like to appreciate nature up close, keep in mind that some activities may be seasonal. For one, whale watching is best between November through May.


5-Day Maui Itinerary at a Glance

As your feet finally reach the ground, arrive in Wailuku and drop off your bags in this laid-back town. Your first day is all about exploring your surroundings, which includes a visit to one of the wettest places on Earth.

Start off the day with a full tank of gas because we’re putting the pedal to the metal! The Road to Hana is an adventurous scenic drive that takes you through the lush landscapes of Maui.

There’s no better way to explore Maui than by foot. Start the day by climbing up the peak of Haleakala and watching the sunrise wash over the island’s highest point. Cool off and reward yourself with a visit to a pineapple plantation.

Take a deep dive and explore the depths of Molokini Crater. Refuel and grab some bites in Wailea before sailing off into the sunset on a charter cruise.

The western coast offers endless activities to fill in your last day in Maui. Go for a hike, swim in the ocean or zipline through the jungle canopy – there’s something for everyone. Brush of the beach sand and end your Maui itinerary with a traditional Hawaiian Luau.

Map of the Itinerary for Maui

5 day maui itinerary map
(Click Map to Interact)

Where to Stay in Maui for the First Time

Beach in Wailuku, Maui

Unless you are hunkering for some luxury resort treatment, get off the beaten path and set up base at Wailuku for easy access to all parts of the island.

While options for accommodations are limited to hostels, private rentals and boutique hotels, the convenience is incomparable.

Located in central Maui, you can access all corners of the island via the main highways (as long as you have a rental car). It’s also in close proximity to the main Kahului Airport (about a 15-minute drive away).

Wailuku may be relatively industrial compared to the holiday resorts of Wailea and Ka’anapali, but it carries a charming small-town feel in certain areas of town.

Better yet, private condos around Iao Valley and West Maui Mountains reap lush surroundings and even friendlier neighbors.

Tip: Familiarize yourself with our Maui travel guide before you dive further into this itinerary!

DAY 1 - Explore Wailuku

The needle in Iao Valley State Park

Begin your 5-day Maui itinerary with the usual “get-to-know-you”. Drop off your luggage at your accommodation, it’s time to explore.

Wander Around

Those who set up base around Wailuku will find initial exploration easy and fascinating to boot!

Rich with Hawaiian history, even revitalization efforts haven’t swept away the mom and pop shops, historical theaters and buildings.

Market Street is a treat, still loaded down with wooden storefronts and local eats. Wander through the southern end to admire plantation-style homes.

Kepaniwai Park

Stroll around Kepaniwai Park for a dose of gardens and history. Built in commemoration of migrant cultures, it’s the perfect hang-out spot – picnic tables, barbecue pits and restrooms are available.

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Iao Valley State Park

Next up is Iao Valley State Park, one of Earth’s wettest places. Waterfalls are gigantic, clouds loom high and heavy; the 2,250-feet tall Iao Needle one of the first things to draw your eye.

Hike up Iao Needle Lookout Trail to enjoy a panoramic shot of this iconic lava remnant; it’s taller than the Eiffel Tower.

Spend the rest of your day checking off attractions in the region.

Soak in Some History & Culture

The Alexander & Baldwin Sugar Museum is great for historians who care for local beginnings; this sugarcane growing community outlines the role of such plantations in Hawaii’s growth.

Those interested in creative arts will find themselves drawn to Maui Arts & Cultural Center, a facility that hosts indoor and outdoor stages. It also houses an art gallery.

Right next door is Maui Nui Botanical Gardens which showcases native plants. Guided tours are available.

Visit a Wildlife Sanctuary & Go for a Picnic

While Kahului doesn’t feature many grand beaches, it does offer Kanaha Pond State Wildlife Sanctuary.

Unlike the rainforests of Maui’s National Park and reserves, this natural area is formed by wetlands. Spot indigenous birds as you meander along the half-mile walk.

Desperate for a taste of ocean breeze anyway?

Hit up Kanaha Beach for picnicking, volleyball and windsurfing areas. Its location by Kahului Airport isn’t ideal, but it’ll do in a pinch.

Turn in for an early night because tomorrow is a long day of driving.

Day 2 - Drive the Road to Hana

coastine of the road to hana

Dedicate an entire day to unveiling the Road to Hana – all 64 miles of it.

Your journey spans the length of Kahului to the town of Hana, various attractions linked by bridges and hundreds of curves. It’s worth the car rental!

Unique roadside stands, black sand, lush rainforest and waterfalls are all en route.

Tip: If you'd rather keep your eyes on the scenery instead of driving the car, full-day tours for the Road to Hana can be booked online. Guided tours usually include transfers and meals.


Prepare for the Day Trip

Before embarking on your coastal adventure, stop by Paia Town to stock up on snacks and coffee. Small organic grocery stores and cutesy boutiques hold everything you might need (or simply want). You can refuel the gas tank if necessary too.

Twin Falls

Take a quick peek at Twin Falls but don’t loiter. The hike is quick and easy, with a coconut water stand that also sells banana bread.

If you’d rather see bigger and louder waterfalls, skip ahead to Mile Marker #10: the Garden of Eden Arboretum.

garden of eden maui
garden of eden, maui

Pua’a Ka’a State Wayside Park

Need to stretch your legs? Stop by Pua’a Ka’a State Wayside Park for a short hike. Refresh at the freshwater pool.

Alternatively, drive straight through to Nahiku Marketplace for yummy food truck eats! Grab some tacos or toasted coconut chips to eat as you wander through the roadside market. Pick up some handmade trinkets and artwork as souvenirs.

Hana Lava Tube

Famous Hana Lava Tube a.k.a Ka’Eleku Caverns is open to self-guided tours every day.

Simple railings guide you through these natural wonders, the layered rocks faces featuring soft moss coverings and layers carved over time.

It’s a great 40-minute activity for visitors of all ages – just remember to grab flashlights on your way in.

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Wai’anapanapa State Park

Next up is the stunning contrast between the cool blue of the ocean and Maui’s black sand beach!

Wai’anapanapa State Park is laden with sea caves and hiking trails, but the one thing not to miss is the black sand beach. The trek down is a loop so enjoy a refreshing dip before continuing your drive.

Explore Hana Town

Roll up into Hana Town (hopefully around 3 PM) for a taste of “real Hawaii”.

Whether you’re busy exploring its attractions or sitting down for an afternoon break, Hana’s all about those chill vibes. You can check out:

Wailua Falls

Wailua Falls is luckily easily accessible and majestic to boot. Cameras are a must if you’re stopping by this 80-feet rush of water.

As Maui’s most photographed waterfall, you can simply enjoy it from the roadside or walk down for a dip in the plunge pool.

Koki Beach

Hit Koki Beach right before sunset and you’ll be blessed with the sight of its unique red sand.

If you’ve never seen dark red sand glow under the orange rays of sun, you’re in for a treat.

That said, there are no lifeguards around, so don’t go in for a swim. You will, however, spot some surfing pros ripping over waves.

Consider staying the night around Hana Town or step on the gas back to your base.

Day 3 - Sightseeing in Maui

haleakala crater

Haleakala National Park

Rise before the sun starts shining because no Maui trip is complete without a Haleakala Sunrise Tour.

Whether you choose to drive up there yourself or join a sunrise tour, know that watching the world wake up at 10,023-feet high is truly something special.

Because it’s become such a popular activity, reservations are needed. It’s freezing up at the summit so pack layers!

Of course, take the chance to explore more of Haleakala National Park.

While the Summit District is known for its crater hikes and gorgeous views, the Kipahulu District brings you into rainforest territory.

Tip: Reservations are highly recommended and tours usually fill up fast. Check Haleakala tour availability to secure your spot!


Here are some top attractions at Haleakala National Park that’s fit for any 5 day Maui itinerary:

  • Seven Sacred Pools – It’s just a short hike to these freshwater pools linked by waterfalls. This Haleakala icon is a must-visit if you fancy palm trees and verdant scenery.
  • Pipiwai Trail – 2 miles of bamboo forest, the hush of waterfalls and a mammoth banyan tree.
  • Kahakai Trail – This short run takes you past archaeological sites to reward with beautiful coastal views.
  • Hosmer Grove – Bird watchers will love this 0.5-mile Loop Trail that brings you through forest and shrub lands. Keep an eye out for honeycreepers.
  • Sliding Sands Trail– A challenging day hike that leads you deep into the crater, it gifts you with the amazingly colored Pele’s Paint Pot some 5.7 miles from the trailhead.

If you decide to spend the day at the National Park, be sure to stay for stargazing – maybe even camp for the night!

A trip to the visitor center is recommended as they will be able to tell you the best trails to set up camp.

pipiwai trail bamboo forest maui sp
bamboo forest, pipiwai trail

Ali’I Kula Lavender Farm

OR Cruise through Upcountry Maui starting with Ali’I Kula Lavender Farm.

On the Western sloping side of Haleakala is this serene patch, complete with 45 varieties of lavender. There’s even a gift shop for you to pick up some scented sleep solutions.

Kula Botanical Gardens

Nearby is the Kula Botanical Gardens for more flora and fauna. Do a short tour around the area before getting back in the car and rolling past pastures.

Visit a Pineapple Plantation

If you have time, sign up for Maui Pineapple Tours. Not only does every person get to takeaway a pineapple, you also learn many interesting facts about pineapple farming.

How many people can boast about knowing the life cycle of Maui Gold pineapples?

Retire to your hotel for an early dinner and well-deserved sleep.

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DAY 4 - Spend the Day by the Shore

molokini crater

Today is your chance to take it slow! After reaching the skies the day before, it’s time to dive deep or relax on a beach.

Molokini Crater

Fuel up with a healthy breakfast because you’re going to be exploring Maui’s underwater riches.

Let experienced guides bring you to Molokini Crater where you can scope out the submerged volcanic terrain. Snorkel up high and peer down 150 feet of clear blues or follow dive masters into its depths.

The coral reefs are an explosion of color, from the spikes of sea urchins to the darting schools of fish. The sunken bowl shape makes it a calm bubble away from the open ocean; you’re perfectly safe.

When you’re ready to be grounded again, Makena State Park’s Little Beach is a secluded oasis for more water activity. You can swim, body board or lounge all you want.

Not satisfied? Nearby Big Beach (Makena Beach) and Oneuli Black Sand Beach offer alternative photo and snorkeling spots.


Wailea is the place to be for late lunch and afternoon fun. More beaches are available for surfing or lounging, such as the famous Wailea Beach.

The backdrop may feature more commercial buildings that further down the coast, but you’ll still have a great time outdoors with Ulua Beach and Polo Beach.

Modern entertainment is plenty too, including The Shops at Wailea, various holiday resorts, beach clubs and an assortment of golf clubs.

Sunset Dinner Cruise

Round off your day with a sunset dinner cruise! Enjoy live music, surf ‘n turf dinner, and boozy drinks while you dance the night away.

Spectacular views along the coast are guaranteed, sometimes with whale sightings too. Most cruises will take you along the western aisle onboard luxury catamarans or a cozier charter.

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Day 5 - Explore the Western Coast of Maui

waihee ridge trail, maui

Spend your last day as busy and as free as you’d like, but turn your gaze towards the western coast along the Kahekili Highway.

Waihee Ridge Trail

Nothing quite wakes you up like a hike, so Waihee Ridge Trail is first on the menu. This scenic 5-mile hike is dramatic, challenging, and more the glorious!

While the trail starts off slow, prepare for its steep rise up past gorges and forest alike.

Mendes Ranch

OR skip Waihee for Mendes Ranch just across the road. They offer both morning and afternoon trail rides along the oceanfront, which lasts between 1.5 to 3 hours.

The horses amble at a comfortable pace, so don’t worry if you don’t have riding experience.

Nakalele Blowhole on the northern coast of Maui
Nakalele Blowhole

Nakalele Blowhole

After all the green fields and red dust tracks, take off towards Nakalele Blowhole. The dramatic gush of water makes a stunning viewpoint but be careful not to stand too close.

For more of these rugged coastal views, head over to the adjacent Nakalele Point Lighthouse.

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Beach Hopping in Kapalua

Kapalua makes it into your front view right around lunch. Meaning “arms embracing the sea”, this pretty resort area sits at the edge of one of Hawaii’s most impressive nature reserves.

It wears beaches and scenic points like a necklace, with Makaluapuna Point, Kapalua Beach, and Napili Bay being the most renowned.

The Honolua Bay Access Trail, while short, paves the way to a beautiful snorkeling spot.

Had enough of water activities?

Why not spend some time at Kapalua Golf – The Plantation Course and brush up on those golfing skills?

Meander Over to Ka’anapali

Ka’anapali is another beachfront destination that offers variety.

From the boardwalk-lined Kahekili Beach Park and Black Rock Beach, to the famous Ka’anapali Beach, this holiday resort location is perfect for some afternoon sun tanning.

For the Artists

Those who are artsy in nature may want Ryan Staub Gallery of Glass on their 5 day Maui itinerary; this glass blowing studio and art gallery combination will stun you with its luxury pieces.

It’s located within Whalers Village, a shopping mall.

For the Adventurers

OR buckle up for an adventure with a zipline tour in Maui! You’ll find yourself zipping through 6 dual sky-high courses, the sprawling ocean opening up in front of you.

Experience a Traditional Hawaiian Luau

Make one last stop at one of the best luaus on MauiAuthentic Hawaiian Luaus are at the beating heart of Hawaiian performance arts and hospitality.

The zing of your tropical cocktail and heady Kalua pig aroma has nothing on the riveting traditional dances. Dive into your bowl of fresh poke, yes, but keep your attention on the story unfolding before your eyes.

It’s time to wrap up your trip. Stomach full and suitcases packed; fall asleep to the gentle lull of Hawaiian waves.

Final Thoughts

Maui’s diverse attractions mean that your trip is what you make of it.

You don’t have to be outdoorsy to enjoy your time on the island; there are plenty of luxury options against trekking through the wilderness.

You can take your days slow, while away hours at small boutiques, spas and cultural experiences.

And if you’re lucky enough to spare a few more days – consider day trips to the neighboring islands too!