The Ultimate 5 day Maui Itinerary: Experience the BEST of the island!

Here you can relax at beautiful beaches, visit cute small towns, drive through the lush rainforests on the Road to Hana, snorkel with sea turtles, go whale watching, chase waterfalls, and even hike on a volcano. In one day alone you could go from a sandy beach to 10,023′ above sea level, which is pretty crazy!

Whether it’s your first trip to Maui or you’re a repeat visitor like us, in this 5 day Maui itinerary we’re sharing how you can experience the best of the island in less than a week. All based on our favorite stops from all three visits!

Before we dive into this 5 day Maui itinerary, there are a few things to know:

• First, this is a fast-paced itinerary. We are more active travelers and love to spend our time doing activities, versus laying out on the beach all day. So many of the days of this Maui itinerary include quite a few stops. If you want a slower pace, you can easily cut out the bigger activities.
• Prepare for some early mornings. We get it, you want to sleep in on vacation. But some of the best things to do on Maui require getting up early. If this isn’t for you, you can easily modify this as well.
• There’s a good amount of driving. The island is broken up into five main areas: West Maui, Central Maui, South Maui, Upcountry, and East Maui. For this itinerary, we’re going to be focusing on one to two areas each day to try to eliminate some driving.
• We’re all about quick eats. Eating on Maui is not cheap. So while on the island we tend to stick to fast casual restaurants and food trucks. Which is what we’ll recommend here! Dining will still be a bit expensive, but you can easily cook or pack your own lunches to save even more money.
• You can easily reorder this itinerary. We did intentionally put some activities on specific days of this trip and also tried to structure it so you have some relaxing days in between the more adventurous days. But you can easily reorganize this itinerary if needed!

One of the most iconic experiences to have while on Maui is to watch the sunrise at the summit of Haleakalā. Watching the sun rise from up here is a magical experience. However, there are a few things to know before you go:

• This requires a very early wake up call. You usually need to be on the road by 3 AM at the latest, depending on where you’re staying. Which is why we recommend doing this the first day, when you’re still on mainland time.
• You need a reservation to visit the summit from 3 AM-7 AM. Reservations are released 60 days in advance and 2 days in advance and can be hard to get.
• It is VERY cold at the top. Being at 10,023 feet, expect it to be in the 30s-40s at the top, plus windy. Make sure to bring layers and blankets!
• You may get fogged out. It took us three attempts to finally see the sunrise. On our first two trips to the island, we got fogged out.
• Can’t get a reservation, prefer to sleep in, or the sunrise weather looks bad? Go for sunset instead! You can still follow this day of our Maui itinerary, but just flip the order.
• Book a tour if you don’t want to drive. If you cannot get a reservation or don’t feel like driving in the dark, you can book a tour to take you to the summit for sunrise.

To learn more about this experience, plus tips on where to actually see the sunrise once at the top, check out our detailed guide to visiting Haleakalā at sunrise. 

Most visitors head back down Haleakalā right after sunrise. But in our opinion, they’re missing out on the best experience in the park: hiking IN the valley! 

The Haleakalā valley is the result of the volcano’s original crater eroding away. It left this 3,000 foot deep, 7 mile long, and 3 mile wide valley that has been carved by water and landslides. And hiking here will make you feel like you’re on another planet!

There are two main trails you can take: the Sliding Sands Trail and the Halemau’u Trail. Both are steep and very exposed trails, but offer a completely different experience. The Sliding Sands Trail truly feels like Mars, while the Halemau’u Trail takes you down this rocky cliffside with both green and red ferns.

For the ultimate experience, we suggest combining both trails into one 11+ mile hike! This route has you starting at Sliding Sands and then cutting across the valley to the Halemau’u Trail. We did this as part of a one night backpacking trip and it was hands down one of our favorite hikes ever!

However, to do this hike, you either need to park a car on both ends or hitchhike. While hitchhiking may seem daunting, it is very common in the park and they even have a designated hiker pick-up spot by the Halemau’u Trail. We got picked up by the first car, but the park ranger told us she has never waited more than 30 minutes. You could hitchhike at the beginning or end, but we suggest parking at the Halemau’u Trail, hitchhiking to the Sliding Sands trail, and then you end at your vehicle. 

One of the most iconic breakfast experiences in West Maui is The Gazebo. This gazebo on Napili Bay not only has amazing views, but delicious breakfast dishes. Our personal favorites are the macadamia nut pancakes (with coconut syrup!) and the fried rice plate.

However, it’s important to know that this spot gets BUSY! They open at 7:30 AM and often have a long line before they open, so you’ll want to arrive by 6:45 AM-7 AM to get seated in one of the first seatings OR just plan to wait a while.

Don’t want to wait in line? You can order take-out starting at 8 AM and then eat it at the beach. For another breakfast option, we hear 808 Grindz is also amazing!

A+K Tip: Parking can be pretty expensive in this area ($20-$30/day), so we suggest finding free street parking. You will be spending quite a few hours in this area, so make sure to find a spot you can park at for hours.

One of the best ways to experience Maui is out on the water! Not only do you get amazing views of the island, but you also get to see the life below the surface. We suggest spending this morning going snorkeling, on a whale watching tour (winter-early spring), or both!

On our most recent trip to Maui, we went on this 5.5 hr La Perouse Bay & Molokini Sea Cave Boat Tour with Blue Water Rafting out of Kihei. And it was SO much fun! It is on a fun zodiac boat (you’ll go fast!) and goes to sea caves that only this company has access to. Plus we got to snorkel in 3 spots, including at Molokini Crater, and swim with sea turtles! There are tons of other snorkel tours you can go on, leaving from both near Lahaina and Kihei.

Most snorkel tours also include whale watching if in season, but if you just want to go whale watching, this 2 hour tour focuses solely on whales.

Want to save money? You can snorkel from many beaches on Maui. Some top snorkeling spots are the Kamaole Beaches and Ulua Beach in South Maui, plus Airport Beach near Kaanapali. Make sure to sign up for the snorkel report from The Snorkel Store to get daily conditions! You can also rent gear from them.

🚨 Safety alert! It is highly recommended to wait at least 24 to 72 hours after landing in Hawaii before going snorkeling to avoid Rapid-Onset Pulmonary Edema (ROPE). We suggest planning to snorkel on the third day, so you’re in the safe window, but also still have two days left in case the weather is bad and your tour needs to be rescheduled.

South Maui has lots of gorgeous beaches to choose from! A few of our favorites are:

• Kamaole Beach Park I. This beach is right by Kinaole and Gus’, making it easy to grab food and enjoy a picnic. Plus it has free parking!
• Makena Beach, also known as Big Beach. As the name implies, this beach is massive, with tons of sand to lay out on. You can also hike up to an overlook to see the beach from above. Just beware, the neighboring Little Beach is a nudist beach. There is also a $10 fee for non-residents since it’s in a state park.
• Keawakapu Beach. This beach has ample free parking and is a great spot for sunset as well!

Today you’re going to drive the island’s famous Road to Hana! This highway winds for 64.4 miles along Maui’s East Coast, connecting the town of Kahului to the town of Hana…and beyond! And it’s famous for its lush scenery and coastal views, plus the road itself, which has 620 curves, 59 bridges (46 of which are one-lane!), and is very narrow in some spots.

Driving the Road to Hana is an all day adventure (12-15 hours with stops), so we highly suggest starting around sunrise. To learn more about the drive and all of the fun stops you can make, check out our ultimate guide to driving the Road to Hana. But here are a handful of our favorite stops!

• The Ke’anae Arboretum to see Rainbow Eucalyptus trees.
• Ke’anae Peninsula for amazing coastal views and Aunty Sandy’s banana bread!
• Coconut Glen’s for delicious coconut milk based ice cream.
• The black sand beach at Waiʻānapanapa State Park. You must make a timed entry reservation to enter!
• Wailua Falls, the tallest waterfall you can see from the road.
• The Pipiwai Trail and ʻOheʻo Gulch in the Kīpahulu District of Haleakalā National Park. Together you’ll get amazing coastal views, get to walk in a bamboo forest, and see a massive waterfall. There is a $30 admission fee to enter Haleakalā National Park, unless you have the America the Beautiful Pass. If you do not have this pass and are paying the entrance fee, we suggest doing the Road to Hana on day 2 or 3 instead, since your entrance fee from visiting the Summit District lasts 3 days.

We’d suggest downloading the GuideAlong – Road to Hana audio tour to navigate you on the road. We have used it every single time we’ve driven the road! The narrator (who is awesome!) shares tons of information, stories, and tips as you drive. And one of the best parts is that you don’t need cell service, it will autoplay based on your GPS position.

A+K Tip: If you have an extra day, we highly recommend staying the night in Hana! It makes the road trip less rushed and more enjoyable. On our most recent trip, we stayed in a cabin at Wai’anapanapa State Park. But we share more options for lodging in this guide! Hana app to guide you through the road. Even when you don’t have service it knows where you are and provides commentary and history about the area, as well as alerts you when to stop.

Day 5: North Shore 

For the final day of this 5 day Maui itinerary, you’ll explore the North Shore! Today will be filled with some beautiful nature, a cool small town, and good eats. It’s the perfect way to end your trip! And if you happen to be flying home on an overnight flight this evening, it’s a great location to spend the day, as it’s close to the airport.

A+K Tip: For those flying home tonight you can store your bags at Island Locker Life or at your hotel (if convenient) while you explore today. And if you need a shower, Island Locker Life offers paid showers or for Planet Fitness members, you can shower there before your flight.

After your hike, head to Iao Valley State Monument. This is home to the 1,200-foot-tall Iao Needle, which is a lush volcanic pinnacle. And it is not only a beautiful place to visit, but also is an important part of Hawaiian history. It was here in 1790 that the Battle of Kepaniwai took place, which was fought between the island of Hawaii and island of Maui.

It’s only a half mile hike to see the Iao Needle, so it’s a quick stop. But you do need a timed entry reservation to visit. If you start your hike at Waihe’e Ridge around 7 AM, we suggest shooting for the 11:15 AM-12:45 PM timeslot. This will give you plenty of time for the hike (~3 hours) and to make the drive over. You are required to enter within the first 30 minutes of your timeslot.

Iao Valley is currently closed due to storm damage, reopening June 26, 2026. It does appear to close often due to damage, so always check its status in advance.

If you have more time to spend in Maui, here are some fun extra activities you could add on to your Maui itinerary! 

• Spend the night along the Road to Hana: If you want to enjoy the road without rushing and beat some crowds, stay the night along the Road to Hana!
• Backpack at Haleakalā: For the experienced hikers, backpacking at Haleakalā National Park is a bucket list experience! We hiked the Sliding Sands Trail to the Palikū Campground and then back out the Halemau’u Trail. The scenery blew us away and the terrain was super varied! Permits are required to camp.
• Take a shelter pup on a field trip: The top thing we want to do on our next trip to Maui is take a Maui Humane Society pup out with their Beach Buddies program. We did this on the Big Island and it was a huge highlight of our trip! It does cost $75 and you need to book it in advance.
• Go on a day trip to Lana’i: Hop on the ferry and spend the day in Lana’i! We suggest renting a jeep upon arriving so you can explore the island.
• Explore more beaches: We share all of our favorites in this post!
• Saturday Upcountry Farmers Market: If you’re on Maui on a Saturday, head to the Upcountry Farmers Market!

Flying to Maui

Maui is home to one airport, the Kahului Airport (OGG), which is located on the northern part of the island. It’s approximately 40-45 minutes to Kaanapali and 20-25 minutes to Kihei. Most major airlines fly to Maui, some with non-stop flights from the mainland and many with layovers in Honolulu.

Getting around Maui

You will definitely want to rent a car while on Maui! Any type of vehicle will work fine, but we do suggest a smaller car if you’re able. This will be a bit easier for the Road to Hana than a giant truck, van, or SUV.

While a sedan or hatchback is likely the cheapest option, if you want to drive in style, rent a convertible or jeep! We have rented both on Hawaii trips before and it’s a lot of fun. But it definitely is a bit more of a splurge!