The Perfect Maui itinerary for 5 days

Hey there, fellow travel enthusiasts!

Are you planning a trip to Hawaii but feeling overwhelmed with all the options? I’ve got you covered. In this article, I’ll be sharing my personal experience and expertise on how to plan the perfect 5-day itinerary for exploring Maui.

As someone who visits Maui every year with my boyfriend, we know exactly what it takes to make the most out of your vacation. With our carefully curated itinerary, you’ll get to witness breathtaking sunrises at Haleakala National Park and drive along the scenic Road to Hana while stopping by stunning waterfalls along the way.

But that’s not all – we’ve also included some exciting activities like luaus and helicopter tours so that you can fully immerse yourself in Hawaiian culture. And don’t worry about wasting time on tourist traps or long routes; our itinerary is designed for maximum efficiency without sacrificing any of Maui’s natural beauty.

So if you’re ready for an unforgettable adventure in paradise, join me as we explore everything Maui has to offer in just five days.

Warning: You might never want to leave!

Where to stay in Maui?

The best accommodations in Maui are on the West and South shores, which have resort towns and local communities. In West Maui, book a hotel in Lahaina or Kaanapali, which have the best luxury resorts and world-famous hotels, such as the Marriott and the Ritz-Carlton. In addition, West Maui is closest to the main beaches and hiking trails you’ll be visiting. 

In South Maui, you’ll want to stay in Kihei, a laid-back community of locals with comfortable Airbnbs that are way cheaper than staying in a hotel. Wailea is another terrific town on the South shore with hotels like the Four Seasons and Grand Wailea. You can expect to be pampered fully in Wailea’s resorts and enjoy a relaxing time. 

Note: Depending on which shore you stay on, flip the days around in the itinerary that suit you best. 

Day 1 – Arrival and Getting Around West Maui

On landing at Kahului Airport (OGG), secure your rental car first. There are nine rental companies at the airport, with a great variety of vehicles. But we recommend getting a 4WD, particularly a Jeep or SUV, for the rough terrain you’ll be traversing (the red convertible can wait.)

West Maui has a lot to explore, so you’ll be visiting great beaches for swimming and snorkeling, exploring lively towns, and even attending a traditional Hawaiian luau. 

  1. Kapalua Beach or Napili Bay Beach – beautiful beaches with stunning views

While your hotel room gets ready, why not hit the beach to kickstart your Maui vacation? Although most people head to Honolua Bay, you’ll want to escape the tourist crowds there and head to these somewhat secluded beaches. 

Located in the island’s Northwestern strip, Kapalua Beach is a hotspot for swimming as the waters are safe and calm. You’ll find families with younger children and lifeguards on duty all day. 

The nearby Napili Bay is a breathtaking sight, with blue waters and a wide sandy shore. There’s a great restaurant, the Gazebo, a short distance from the shore, where you can stop for a delicious brunch with ocean views. 

  1. Nakalele Blowhole – Maui’s natural blowhole 

A bit farther off from the main island strip is the Nakalele Blowhole which has geysers producing a shower 15-20 ft. in height. The hike to the blowhole is the Nakalele Lighthouse trail, that’s short, easy, and accessible to everyone. 

The blowhole is best viewed during the high tide, as the water shoots up even higher than usual, spraying those that get too close. However, you can also get great pictures next to the blowhole, as it stays in the air for quite some time. 

Don’t forget to get some delicious homemade banana bread on your way back from a local selling it in the parking lot. 

  1. Ka’anapali Beach and the nearby Whalers Village

Aside from resorts, Ka’anapali has a gorgeous beach, with a famed cliff diving spot called Black Rock. If you’re not up for the adventure, Black Rock also offers the best snorkeling spot in West Maui, as there’s a natural coral reef in its depths. You can swim alongside tropical fish, Hawaiian green sea turtles, and various other sea creatures. 

After the beach, head to the nearby Whalers Village, Maui’s only oceanside retailer market. You can find luxury brands alongside local retail stores here and an expansive food court. Whalers Village is a great spot to have a delicious meal from famous restaurants like MonkeyPod Kitchen and the local favorite Leilani’s on the Beach.

  1. Attend the Old Lahaina Luau

The best way to get into the Hawaiian feel is by attending a luau, a traditional event comprising hula dances, performances, fire shows, fun activities, and a great dinner afterward. The Old Lahaina Luau is the most famous in Maui, with an elaborate hula, a storytelling segment on Hawaiian history, and unlimited drinks throughout. 

The dinner is a tasty buffet that’s made even better by the oceanside seating and sunset views. However, the Old Lahaina Luau is famous amongst tourists and sells out quickly, so make sure to get your reservations well in advance.

  1. Walk around the lively Lahaina Town

There’s nothing better than ending the day with a walk in Maui’s vibrant streets. Lahaina is filled with shopping centers, eateries, and vendor stalls on its famous Front Street. In addition, you can walk by art galleries, go window shopping, and enjoy music from street artists. 

Although it’s a definite tourist attraction, the atmosphere is fun, and the area is very well-maintained. We recommend trying the Hawaiian shaved ice for dessert from street vendors, with lots of yummy flavors. And if you skipped dinner at the luau, grab a bite from restaurants like Lahaina Grill, Fleetwood’s, and Cheeseburger in Paradise, which have the most delicious food. 

Day 2 – Road to Hana and Exploring East Maui

Your Maui trip is incomplete without driving the Road to Hana, which has the most beautiful beaches, waterfalls, and towns lining it. The road trip requires two days to complete every stop, so you can spend the night at Paia or Hana towns. We recommend only taking select stops and enjoying each one fully, so you don’t spend half the day on the road. 

  1. Start your journey from Paia town (first stop on Road to Hana)

Paia is a small town on the Road to Hana, with chic boutiques, galleries, and local restaurants lining the streets. Some people refer to Paia as a hippie town, as you can find yoga studios, day spas, and fitness centers here. 

We love stopping by Mana Foods, a grocery store with organic foods and snacks in bulk (think Whole Foods but better), and a deli counter serving delicious fresh sandwiches and coffee. If you don’t have your beach fit sorted yet, shop from the boutiques selling amazing sundresses and beachwear at reasonable prices. 

  1. Ho’okipa Beach Lookout (mile marker 8.8)

The Road to Hana has great beaches with beautiful coastal views, especially Ho’okipa Beach, which has a gorgeous lookout point with views of the Pacific Ocean and Maui’s coast. This is a famous spot for windsurfing, with annual tournaments and local surfers showcasing their skills in the waters. 

If you don’t want to take the trail down to the beach, stand by the lookout point to enjoy the scenery, and park your cars in the nearby lot. However, don’t miss Ho’okipa Beach on your way back, as the sunset here is breathtaking.  

  1. Garden of Eden (mile marker 10.5)

With more than 500 species of tropical plants, flowers, and fruit trees on display, the Garden of Eden Botanical Gardens is a must-stop for nature lovers. These were the filming site of the Jurassic World movies, owing to the lush forest scape and tall rainbow eucalyptus trees visible from afar. 

You’ll only be spending between 30 minutes to an hour here. The gardens provide a panoramic view of the Puohokamoa Falls and have many domestic animals like ducks, geese, chickens, and horses wandering around. Also, make sure to get some yummy snacks and drinks from the local food trucks in the parking lot on your way out. 

Note: There’s a small entrance fee for the gardens.

  1. Swim in the Upper Waikani Falls (mile marker 19)

On the Road to Hana, you’ll see cars parked on a bridge near the highway. That’s the lookout point for Upper Waikani Falls, three falls of varying heights, also known as the Three Bears. The falls have a wide pool at their base that’s perfect for swimming, and you can also wade to a spot directly under the falls. 

A trail goes down to the falls, beginning from the bridge. Fortunately, most people only view from the lookout point above, making the falls secluded. However, the scenery below is beautiful, and a swim in the falls is unmissable. Just make sure to trek in dry weather, as rainy spells can make the trail slippery. 

  1. Waianapanapa State Park – Black Sand Beach and blowholes (mile marker 32)

On the farther end of Road to Hana is Waianapanapa State Park, home to the stunning Honokalani Black Sand Beach, many wet caves, and lava tubes you can wander in. The beach is a gorgeous stretch of black sand (fine lava rock) and blue-green waters that offer a refreshing swim. 

There’s also a blowhole in the State Park and many beautiful photo ops all around. We like to pack lunch and have a picnic on the beach. There’s usually a crowd on the shore, but walk a bit further, and you can find a quiet spot. However, the lava sand is rough, so keep your shoes on at all times. 

Note: Waianapanapa State Park requires reservations beforehand, and there’s a $10 entrance fee.

  1. Oheo Gulch and the stunning Pipiwai Trail (mile marker 42)

The Haleakala National Park is near the end of your road trip, with beautiful waterfalls, dense forests, and hiking trails leading to them. You can drive to the Oheo Gulch waterfalls inside the Park, which consists of seven spacious pools to swim and dive in. 

These falls are undoubtedly the most beautiful in Hawaii, and a sacred spot for Hawaiians. 

However, the falls are closed during extreme rains as they can overflow. 

In that case, hike the Pipiwai Trail, which moves through a dense bamboo forest, passes by the Oheo Gulch from above, includes many streams, and ends at the Waimoku falls. The four-mile round trip is a must-visit for everyone, as it’s a breathtaking path through the Hawaiian jungles.

Tip: The Haleakala State Park charges a $30 fee to explore the area for three days, so come here the next day for the sunrise.

Day 3 – Haleakala National Park and Upcountry Maui

Your third day in Maui will start with a sunrise over the Haleakala Crater, followed by a nature walk through the gardens of Kula. Afterward, explore Upcountry Maui, its quaint towns and beaches. And if you’re up for it, a helicopter tour over the island!

  1. Haleakala Sunrise (stunning aerial views of Maui)

The Haleakala Crater is the most popular spot worldwide for watching the sunrise. At a 10,000 ft. elevation, the view here is unmatched. You’ll have to get reservations for the hike and drive out well before dawn to reach the top in time. 

The State Park only allows 150 people at a time for the sunrise, so you can enjoy some privacy at the top. Don’t miss a photo-op at this spot, as the golden rays lighting up the countryside and coasts is a truly unforgettable sight. 

Tip: Pack warm clothes for the top, as it can get chilly at the height.

  1. Enchanting Floral Gardens in Kula 

Nestled on the slopes of Haleakala, the Enchanting Floral Gardens in Kula display 1,500 species of tropical and subtropical plants and flowers from Hawaii and worldwide. You can take a walking tour through the fruit trees and multiple gardens, with a wide variety of exotic flowers such as orchids, hibiscus, and jade vines. 

The gardens host farmers markets, live music performances, handicrafts exhibitions, and hula shows throughout the week. In addition, you can buy homemade food from locals and enjoy it on the Gardens’ many gazebos with views of the natural scenery. 

There’s also a small entrance fee to enter the garden.

  1. Makawao Town in Upcountry Maui 

Drive to Upcountry Maui to the historic Makawao Town, once home to Hawaiian paniolos and now displaying art galleries, chic boutiques, and local eateries. Walk along Baldwin Avenue in the town’s center, next to buildings from the early 1900s, where Japanese and Chinese families used to run businesses. 

The Komoda’s Store and Bakery is a great place in town, where you can try the best cream puffs in Maui, baked fresh every day. You can also stock up on fresh produce and snacks from its grocery section. 

Don’t leave the town without grabbing a delicious lunch from Casanova, a local favorite eatery serving authentic Italian pasta, pizzas, and seafood specials.

  1. Visit the Kanaha Beach Park in Kahului (secluded with beautiful views)

Traveling all day can get exhausting, so bring your activities to a halt with some peaceful time at Kanaha Beach Park in Kahului. This beach is close to the airport, about ten miles, but free from tourist crowds as it’s not well-known. 

You can enjoy a relaxing swim in the calm waters or take a walk on the sandy shores. There are shady trees here, with picnic tables set up underneath, so enjoy a quiet meal with beachside views. 

  1. Take a Helicopter Tour over Haleakala and Hana

Exploring the vast Maui shores can get tiring, and the long drives and nature hikes aren’t for everyone. Take a helicopter tour for these reasons and to experience Maui’s beauty through an aerial adventure. There are many tours going over different parts of the island, but we recommend taking the Air Maui tour over Haleakala and Hana. 

The 45-minute helicopter ride will take you over Hana’s dense forestry, over waterfalls unreachable by foot, and coastal views at a 10,000 ft. elevation of the Haleakala Crater. The pilot is friendly and gives great information about the land below. Although the tours are more expensive than a road trip, they give an unbeatable view of the island and are an unmissable photo-op.

Day 4 – Central and North Maui

Central Maui and the Northern coast are often overlooked by most guides, as they’re considered small with not many attractions. However, this itinerary will take you through the Waihee Ridge Trail, the Iao State Park, and other famous island spots, all beginning in the Central and North of Maui.

  1. Waihee Ridge Trail

One of Maui’s most spectacular hikes, the Waihe’e Ridge Trail, is an excellent way to explore the island scenery from an aerial view. The roundtrip on the trail takes 2-3 hours, and you’re met with views of the coast and beautiful forestry on your trek. 

As the trail is steep, you don’t have to hike all the way up. Instead, sit on benches along the way to take a break and admire the surrounding greenery. However, if you can make it to the top, a raised viewing platform provides stunning views of the Maui and the nearby Makamakaole Falls. 

Note: Don’t visit in the rainy season, as water makes the trail slippery and difficult to traverse. 

  1. Iao Valley State Park (beautiful forestry and the Iao Needle)

The Iao Valley State Park is nestled in the lush greenery of the Iao Valley in Central Maui. Here you’ll find the natural rock formation called the Iao Needle, a green-covered stone protruding from the valley floor at 2,250 ft. above sea level. 

There are lovely walkways and botanical gardens surrounding the Iao Needle, where visitors can explore the natural scenery. You can also find waterfalls, rushing streams, and small water bodies safe for swimming scattered through the State Park.

Note: There’s a $10 parking fee for cars and $5 per person.

  1. Baldwin Beach (great family-friendly beach)

One of the most popular beaches in Paia, HA Baldwin Beach, is a terrific spot for families, with soccer and softball fields, a picnic pavilion, barbeque stations, and clean amenities. The water is usually good for swimming but gets rough in harsh weather, in which case children should be kept out. 

The beach is a great spot for surfing and boogie boarding, and locals will help you in learning some fun moves on the waves. However, the beach gets crowded with locals and tourists on weekends, so try to visit during the weekdays instead.

  1. Maui Tropical Plantation

A trip to Maui Tropical Plantation is unmissable if you want to explore the island’s plantation history of pineapple and coconut farms. You can take a walking tour of the lush plantation grounds or a guided tour on a tram that goes through the beautiful landscape. 

We found the tour very informative, including driving through diverse fields of pineapple, papaya, mango, bananas, avocado, coffee, and a live demo of a coconut being husked. Afterward, you can buy island goods like bags of freshly ground Kona coffee from the gift shop. 

Enjoy dinner at the terrific onsite restaurant, Cafe O’ Lei at the Mill House, which serves delicious farm-to-table food grown on the plantation. 

  1. Maui Ocean Center (see Hawaiian sea life all in one place)

The Maui Ocean Center is one of the largest aquariums in the US, housing indigenous Hawaiian sea creatures, like tropical fish, sea turtles, sharks, stingrays, octopuses, and sea jellies, among many others.

They have terrific displays like the Whale Exhibit, where you get a realistic humpback whale view from a 3D screen. Also check out the Open Ocean Exhibit, which includes walking through a plexiglass tunnel as sharks and stingrays swim around you. 

Tip: Try to visit during the afternoon or evening, as the exhibit gets crowded during the day with families. 

Day 5 – The Gorgeous South Maui

Your final day in Maui doesn’t have to be all about getting ready for departure. Just follow the itinerary for great places to visit around the island including beach bumping, snorkeling, and enjoying a sunset cruise. 

  1. La Perouse Bay (lava rock and a stunning beach)

La Perouse Bay is a famous South Maui beach located close to the Makena State Park and the last beach on the South shore. The bay houses natural blow holes and is surrounded by expanses of lava rock. A trail made of volcanic rock leads to the beach from the parking lot. However, wear hiking shoes to cross the trail as the rocks are uneven.

Once on the bay, enjoy swimming and walking on the sandy shore. La Perouse Bay is a favorite spot for dolphins and tropical fish to cross, so snorkeling is enjoyable here. You’ll also run into local fishers who let you fish with them for sport. 

  1. Visit Molokini Crater or Turtle Town

There are terrific cruises on the South shore that go to the Molokini Crater, where there’s a natural reef and abundant marine life, and Turtle Town, home to Hawaiian sea turtles. You can book a cruise with the Kai Kanai company in advance, as they get full soon. 

The cruise takes off in the late afternoon and includes a stop at various marine life hotspots in the ocean. You’ll be traveling on a beautiful catamaran cruise with well-trained staff and tasty snacks and drinks during the trip. Once at the Crater, you can snorkel alongside native marine life and see a spinner dolphin show as well. 

Tip: If your trip falls from November to March, book the whale-watching tour, which includes cruising next to humpback whales.

  1. Beach Bump on the Gorgeous South Shore Beaches 

Beaches on Maui’s South shore are famous for their scenic views since each one stretches for miles, with golden-white sands and calm waters perfect for swimming, snorkeling, surfing, and other great water activities. Some great beaches on the South shore are Chang’s beach, the Kamaole Beaches (I, II, and III), Big Beach and Little Beach in Makena State Park, and Secret Cove.

The Makena Big Beach is great for water sports, and Little Beach is ideal for families, as the water is safe. They also provide great views of the nearby Molokini Crater. However, these beaches are always crowded with tourists, so head to Secret Cove past Makena, which is secluded with wide sands to relax on.

  1. Have dinner in Wailea or Kihei towns

The best way to end a day of sand and sun on the South shore is with a delicious dinner at island-famous restaurants. You’ll find great eateries in uptown Wailea, like the Maui favorite MonkeyPod Kitchen, authentic Italian food at Matteo’s Osteria, and the best steaks in Maui at Ruth’s Chris Steakhouse. 

For delicious Hawaiian food, the places in Kihei are unmatched. You’ll find local favorites like Kihei Caffe, which serves the best loco moco. Coconut’s Fish Cafe is another popular spot for its seafood mains made from fresh catch.

Make sure to get dessert from Ululani’s Hawaiian Shaved Ice, a local favorite spot for their shaved ice topped with natural flavoring made from fresh fruit.

  1. Attend the Te Au Moana Luau

I love to end a trip with the most exciting activity, and luaus are perfect for that. The Te Au Moana Luau at Wailea is a great experience for everyone, as the event is family centered. The luau, hosted by the Wailea Marriott, is an open-air show and boasts gorgeous sunset views.

There are fun activities during the luau like making leis, which you can wear for the rest of the show. The hula dances by Polynesian performers are incredible, and the dancers take you onstage with them as well. Plus, the performances are followed by a delicious buffet dinner. 


Is 5 days enough for Maui?

Spending 5 days in Maui is perfect since you can explore each shore in a single day and still have a day left to plan your own activities. However, the Road to Hana in East Maui is a long trip, so we recommend spending at least two days on the road to fully experience the gorgeous landscape.

How many days should you spend in Maui?

On average, travelers stay in Maui for eight days, as the island is pretty big. However, you can also go around Maui in five or seven days since the roads are well-connected and it doesn’t take long to reach most places. 

What is the best month to go to Maui?

The best months to visit Maui are April and May and September through November. That’s because the spring and fall seasons promise pleasant weather, which every vacationer seeks, alongside lower rates and an absence of tourist crowds that usually hit in summer and winter.

Is Maui better or Honolulu?

Although both islands are perfect for a truly Hawaiian vacation, it depends on what you’re looking for. Honolulu in Oahu promises a cosmopolitan city with crowded malls, beaches, restaurants, and vibrant nightlife. On the other hand, Maui has the island’s natural scenery, lively towns, gorgeous secluded beaches away from crowds, and lots of nature hikes. 

Concluding the best 5-day Maui Itinerary

Planning a vacation in Hawaii can appear intimidating, especially if it’s your first time on the island. However, after going through this itinerary, you’ll know the process is simple and only requires a few calls and reservations ahead of the trip.

In just 5 days, you can make your way around the expansive Maui island, visiting sandy beaches and swimming in clear waters alongside marine life. Aside from these, the towns of Paia, Lahaina, Wailea, and Kihei offer great shopping, eateries, historical sites, and local activities to enjoy. 

Remember to come prepared for a glorious road trip on your Maui vacation, as most places are accessible by land and offer breathtaking views of the Valley Isle throughout.

Your 5-day trip in Maui will be a memory to remember!

Last Updated on July 11, 2023 by Brigitte