Perfect 5 Day Maui, Hawaii Itinerary You’ll LOVE

Since Florida is our home base, getting to Hawaii is NOT an easy place to get to for us. So we are really committed to making the most of our time there when we do go.

All of that to say that a lot of planning went into this itinerary. We have personally been to Maui multiple times with our kids in order to make this 5 day itinerary.

It is our opinion that this really is the best 5-day itinerary for visiting Maui and we hope that it helps you maximize the time you have on the island while ensuring plenty of down time, too.

We do typically stay on Maui for around 7-10 days. In general, it’s my opinion that more time is always better. But time is a luxury that we don’t always have, so that’s why I built this itinerary for 5 days.

If you plan to stay longer than 5 days in Maui, this is still a great itinerary for you because I’ll include some other options to fill your days. Also, many people do enjoy relaxing at the resort pool or beach which you can easily add into this itinerary or in your extra days in Maui (if you have them).

Day 0: Arrive to Maui

You will fly into Kahului (OGG). Last time we visited Maui, we landed in Maui around 3 pm.

By the time we got off the plane, got our luggage, and got the rental car, it was close to 4:30, which isn’t too bad.

We went to Target for essentials before heading to our Airbnb which was around an hour away from the airport.

There is a WalMart, Target, and Costco close to the airport. Stopping here for the essentials (for us, that was breakfasts, snacks, diapers, and wipes) can help to keep the costs down.

If you’re anxious to get to your destination, we found that there are plenty of grocery stores throughout the island as long as you’re staying in one of the main areas (which you probably are).

Chances are, you had a pretty long travel day so on your first day, it can be nice to grab dinner and get settled. Enjoy the beach if you’re in walking distance, jump in the pool if you have one or go for a walk around the area you’re staying.

Day 1: Haleakala Sunrise and Explore Wailea + Kihei

Your first day will be an early one, but that shouldn’t be a problem for most visitors because of the time change. We’ll start our morning on the mountain but end it exploring the beach towns of Wailea and Kihei.

Or, if you’re staying in those areas, feel free to swap with day 2 and explore West Maui instead.

Sunrise at Haleakala National Park

Day one in Maui will start with an early morning to watch the sunrise at Haleakala National Park. This is one of the most popular things to do on Maui.

Haleakala National Park is the highest peak in Maui. It’s over 10,000 feet above sea level and can be seen from pretty much wherever you are on the island. It is a dormant volcano that last erupted around 1790.

While you can visit Haleakala National Park anytime, sunrise is the most popular. Ideally, you’ll get there when it’s still dark then you’ll watch the sun come up from the top of the mountain.

If you visit for sunrise, reservations are required. You must have reservations to enter the park anytime between 3:00 am and 7:00 am but if you are visiting after 7:00 am, you do not need a reservation.

Some people prefer to visit at sunset for this reason. I’ve also heard that they like staying after dark to see the stars, so then you get the sunset and stargazing, which is pretty magical.

Another benefit of going to Haleakala for sunset is that you’ll be driving up the mountain in the daylight. When you’re driving down in the dark, it will be slightly more familiar.

To determine when to leave your accommodations for the sunrise, you can check Maui’s sunrise times. The sunrise will depend on the time of year and can range from 5:30 am to 7:00 am.

Driving to the summit will take a few hours, depending on where you are staying. Here are approximate times to the entrance (it’s an additional 30 minute drive from there):

• Kahului – 2.5 hours
• Wailea – 3 hours
• Kaanapali – 3.5 hours

Reservations open 60 days in advance at 7 am Hawaii time. They do sell out quickly so if you know when you want to visit, go ahead and book. If you’re not able to get tickets when you want them, they also release a small amount of tickets 2 days before the date at 7 am Hawaii time.

If you don’t get reservations, you could always book a tour to see the sunrise at Haleakala. The tour companies will cover the reservation process for you but they are more expensive than going on your own.

Pro tip: When you’re trying to buy tickets, create an account and make sure you are logged in. This is especially helpful if you’re trying to get tickets when they are released 2 days ahead of your date (these ones get scooped up fast). You can only add a ticket to your cart and proceed if you’re logged in so this decreases the risk of someone “stealing” your tickets from you.

Also know that it gets chilly up there, so you’ll want to bring warm clothes.

We also did the Hosmer Grove trail, which was a little over a half mile and very easy. It was a perfect hike to do with our baby and toddler.

We also stopped at the Kalahaku Overlook and the Leleiwi Overlook on our way to the summit.

We didn’t do this, but the Sliding Sands Trail is a very popular trail at Haleakala. You start at the summit and go down into the crater. A lot of people will do one switchback then hike back out but you could do up to a full-day 11 mile hike.

I have a full guide on Haleakala National Park (coming soon).

Wailea and Kihei

After your morning at the Haleakala summit, I would head to explore Kihei and Wailea. Kihei and Wailea are approximately 10 minutes apart from one another but have different vibes.

Kihei is a smaller laid-back beach town with reasonably-priced accommodations for Hawaii standards.

Wailea has good beaches, fancy resorts, upscale restaurants and shopping, golfing, and good outdoor activities. Wailea Beaches are incredible but tend to be a bit more crowded.

Things to do in Kihei:

• Kihei Caffe or Nalu’s for breakfast
• For a more inexpensive meal (by Hawaii standards), you could eat at one of the food trucks at Kihei Food Truck Park.
• Humpback Whale National Marine Sanctuary 
• Maui Brewery (there is also one in Ka’anapali but this one is better)
• Visit South Maui Gardens – a botanical garden with lush tropical plants, walking paths, and one of Maui’s best food truck gatherings.
• Fourth Friday Celebration – if you happen to be visiting on the 4th Friday of the month, check out the Friday Celebration. It’s held at Azeka Mauka Shopping Center from 6 pm to 9 pm and there are vendors (food and art), live entertainment, games, and more.

Some Beaches in Kihei:

• Kamaole Beach Park – There are actually 3 beaches that make up Kamaole Beach Park. They are named Kam I, Kam II, and Kam III.
• Mai Poina – a mile long but not the greatest for swimming due to the waves
• Keawakapu Beach – Called “Hidden Cove”, more low-key and off the beaten path
• Kalepolepo Beach – Best for seeing whales when it is whale season
• Waiohuli Beach – one of the smallest beaches with shallow, clear water
• Sugar Beach – One of the longest stretches of beaches in South Maui with views of three islands (Lanai, Molokini and Kaho’olawe)
• Maalaea Beach

Things to do in Wailea:

• Akamai Coffee for coffee and good breakfast options
• Monkeypod Kitchen for lunch or dinner (famous for their mai tais and pizza)
• Walk the Wailea Beach Path. It is 1.5 miles long and crosses several different beaches in the area. If you’re not staying in the area, you can find parking at Ulua Beach or Polo Beach.
• Wailea Farmer’s Market on Tuesday mornings from 8 am to 11 am at Wailea Village. They also have an evening market on the 4th Thursday of each month from 4pm to 7 pm.
• Shops at Wailea for some good shopping
• Golfing at Wailea Golf Club
• Birdcage Bar for cocktails

Some Wailea Beaches:

• Makena Beach, also known as Big Beach, is my favorite. Do be careful getting in, though, because the waves here can be intense.
• Little Beach, next to Big Beach, is a clothes optional beach
• Keawakapu Beach
• Wailea Beach is one of the main beaches so it can be crowded but the sand is soft and the waters are calmer
• Ulua Beach is a smaller beach great for snorkeling

Day 2: Snorkel or Whale Tour

Your second day in Maui is also going to start pretty early. Not quite as early as yesterday, but today we are going snorkeling.

The best snorkeling in Maui happens earlier in the morning because that’s when the waters are calmest. Maui has some of the best snorkeling, even just off the beach.

But one of the most popular places to snorkel in Maui is at Molokini. It’s a sunken volcano with crystal clear water. You can get visibilit up to 150 feet!

And Molokini is a sight to see in itself; it’s a crescent-shape “island” jetting out of the water. Fun fact – the volcanic crater is 230,000 years old!

Instead of snorkeling, you could go on a whale tour if it’s whale season. Seeing whales is one of the best things to do in Maui! The season is from January to March but you may see whales a little bit before or after that.

Day 2: West Maui: Nakalele Blowhole, Kaanapali, and Kapalua

Now it’s time to explore West Maui!

The Nakalele Blowhole was one of my favorite parts of our trip to Maui. We drove from the Kaanapali area to the blowhole.

The drive from Kaanapali to the blowhole was stunning. There are tons of places you can pull over to get good views and there are also some hikes and beaches on the way.

I get nervous on windy mountain roads, so there were a few times I was a little nervous. But I genuinely think most people wouldn’t be nervous at all on this road.

The road was well taken care of and paved. There are turns but they aren’t too sharp and there are guardrails throughout the drive.

But do note that if you keep driving past the blowhole headed southeast, the roads get very scary. Picture one lane roads for traffic both ways to share with the side being a cliff straight down. We didn’t chance it or try to go that way.

Getting to the blowhole is very easy, there’s really only one road that leads there and there are signs leading you. But you do have two options for parking, one parking lot is at mile marker 38.5 and the other is at mile marker 38.

We chose mile marker 38.5 because this allows you to view the blowhole from the top without having to hike. From mile marker 38, you’ll actually take a 1.25 round-trip hike for a closer view of the blowhole.

The blowhole that you’ll see is basically a hole that causes water to crash into the air when the ocean water hits it. It’s similar to a geyser and the water can reach up to 100 feet high.

This is very, very cool but it can also get dangerous. The waves can sneak up on you and pull you in; a good rule of thumb is to stay where it’s dry. If you’re wet, you’re too close.

Things to do nearby, in the Kapalua Area:

• Get breakfast at Gazebo – I highly recommend the fried rice and white chocolate macadamia nut pancakes. The line here gets very long, so be prepared to wait. We usually get it to go and enjoy the nearby beach.
• Kapalua Coastal Trail is a trail along the coast. It’s 3.5 miles round trip. You go in and out, so it’s a little over 1.7 miles one way but you can turn around anytime. The trail is relatively easy but not really stroller friendly as you’ll cross some lava fields and other rocky terrain at times. You’ll have gorgeous views!
• Burger Shack for lunch. It was the best service we had on the island and the views are out of this world. They have alcoholic milkshakes and their food is delicious.
• Kapalua Bay is one of the most beautiful beaches. It was voted as “America’s Best Beach” by Dr. Beach in 2018. It is great for swimming, has calm waters, and good snorkeling.
• Napili Bay is another really popular beach in the area. It is known for its crescent-shaped shoreline, calm (and gorgeous) water, and excellent snorkeling when conditions are calm. There are also frequent sightings of sea turtles just offshore.

Things to do in the Kaanapali Area:

• Kaanapali Beach is a gorgeous beach that stretches over 3 miles
• Black Rock is on the north end of Kaanapali Beach and is well known for great snorkeling
• Eat at Monkeypod for lunch or dinner (yes, this is also mentioned in Wailea – there are two locations on Maui)
• Dukes is also a great option for lunch or dinner with amazing water views
• The Sheraton Maui Resort has a cliff diving ceremony every night where someone dives from the cliff (known as Black Rock) into the water.
• Whalers Village is an open air shopping area
• Kaanapali Beach Walk is a paved walking path in between the resorts and the water. I love looking at all the resorts and also taking in the gorgeous landscaping and water views.

Day 3: Iao Valley State Park

Iao Valley State Park is breathtaking and also easily accessible, making it a great spot for everyone to enjoy. Even if you don’t leave the parking lot, you’ll get a gorgeous view.

It is the second wettest place in Hawaii so everything is very green. And the moisture flows into the Iao stream, which you can take a very short hike to see.

We took our time here and still only spent around 90 minutes, so it doesn’t take long to explore.

You do need reservations to visit, but we didn’t have a problem getting them around an hour before we visited.

If you have time before or after, I recommend checking out Wailuku. It’s a really charming town with some cute shops, coffee, and restaurants.

While you are in the area, here are some other things you could do:

• Maui Tropical Plantation has 60 acres of fruits and plants. You can take a guided tour of the farm and they also have coffee tasting. There is also a restaurant.
• Alexander and Baldwin Sugar Museum has information and exhibits on the sugar industry in Maui

You’re also not too far from the heliport while you are here. Taking a helicopter tour in Maui is on my bucket list, but we didn’t get to do that on this trip. If it’s something you want to do, it would be easy to do before or after a trip to Iao Valley State Park.

The rest of today is a perfect time to relax because our last full day in Maui will be very busy.

Day 5: Road to Hana

Road to Hana is one of the most popular things to do in Maui.

It’s basically a road trip to the town of Hana. Along the way are lots of stops where you’ll be fully immersed in Maui’s natural beauty. Things like waterfalls, food trucks, nature trails, hikes, parks, and more.

The Hana Highway is only 64 miles, but it is full of hairpin turns and one-lane roads. So the drive takes a couple of hours with no stops. But trust me, stopping is the whole point!

If you’re nervous about driving, you can book a Road to Hana tour. They’ll do all the work for you by driving and you’ll get to check out some of the most popular stops as well as some lesser-known stops.

If you have some extra time, this is where you might want to spend a little more time. Most people do the Road to Hana as a day trip which can make for a really long day (often people spend around 13 hours when they do it all in one day).

If you have the time to stay overnight in Hana, I highly recommend the Hana-Maui Resort by Hyatt.

Pro tip: Be aware of the weather and be willing to pivot plans if there’s bad weather. They will close roads if/when they become unsafe and the Road to Hana is not a place you want to be if the weather isn’t good.

Here are some of the most popular/best stops on the Road to Hana:

• Twin Falls
• Garden of Eden Arboretum
• Keanae Valley Overlook
• Waikani Falls
• Aunty Sandy’s (for banana bread!!)
• Wailua Falls
• Hamoa Beach
• Black Sand Beach
• ‘O’heo Gulch – 7 Sacred Pools
• Pipiwai Trail

A Few Notes and Tips on Visiting Maui

A lot of places are closed on Sundays, especially restaurants. You’ll still find plenty of options open but if there’s a place you really want to try, make sure to check their hours ahead of time.

We all love sea turtles (called honus in Hawaii) and hope to see them. But don’t get too close. They are rightfully protected and it is illegal to touch them.

Unless you plan to stick around your resort, you’re going to need a car. And I highly recommend exploring Maui outside of your resort.

Popular activities that you’ll need reservations ahead of time for include:

• Haleakala National Park (for the sunrise only – if you are visiting after 7 am, then you won’t need reservations)
• Mama’s Fish House for some of the best food on the island
• Wai’anapanapa State Park where the famous Black Sand Beach is on the Road to Hana.
• ʻĪao Valley State Monument

Where to Stay in Maui

When I was doing my research on Maui, I got a little overwhelmed trying to figure out where to stay. I actually have an entire post about where to stay in Maui.

But here’s the short version: Everyone’s preferences will vary.

More than likely, you’re going to be choosing between Kaanapali, Kihei, and Wailea.

Kaanapali has great snorkeling and tons of resorts. It isn’t quite as accessible to the rest of the island but this is where we stayed and we absolutely loved it. Some popular places to stay in Kaanapali are:

• The Westin Maui Resort and Spa
• Hyatt Regency Maui Resort and Spa
• Sheraton Maui Resort and Spa

Wailea is a more upscale area that also has tons of resorts. It’s just south of Kihei. I like Kaanapali for families and Wailea for a more romantic getaway. Some popular places to stay here are:

• Grand Wailea, A Waldorf Astoria Resort
• Wailea Beach Resort by Marriott
• Andaz Maui at Wailea
• Four Seasons

Kihei is more centrally located and has more budget-friendly (by Hawaii standards) short term rental options.

You’ll also more than likely hear about Paia, Kahului, and Hana.

Paia might be nice for one night if you have the time and don’t mind switching hotels.

It’s a cute hippie/surfer town but isn’t where you’d want to be based out of. You can see the whole town within a day or so, the beaches there are pretty rough, and it’s the last town before you start on the Road to Hana so traffic can get congested.

Kahului is where the airport (OGG) is located and where you’ll fly in. It’s more commercial and where the things are located that people need in order to live on the island like Costco, Target, WalMart, etc.

Hana is a great place to stay for one or two nights in order to properly explore more sights on the Road to Hana. But it’s not a good base for the whole trip because it’s not easy to reach.

Are You Read for Your Maui Vacation?!

There is something so magical about the Hawaiian islands.

And the island of Maui offers so much to do. This 5-day Maui itinerary should give you a good mix of sightseeing mixed with relaxation but you can mix and match as much as you want to make it your own.

Five days in Maui is definitely enough time to experience a lot on the island.