5 Days Maui Itinerary

Maui Itinerary – 5 Days

Maui 5-Day Itinerary: How to Spend 5 Days on Maui

Maui is an island filled with natural wonders and it’s perfect for exploring during your vacation there. Maui really does have every element of a dream vacation; perfect beaches, wildlife, incredible hikes, and delicious Hawaiian cuisine. I have compiled the perfect Maui 5-Day Itinerary for you, taking the hassle of planning out of your vacation so you can just enjoy your time exploring Maui. Whether it’s your first time on the island, or you are a return visitor, there’s always something new to explore here.

Best time to visit Maui

The winter in Maui is from November until March, and the island typically gets a lot of rain during this time, which can make some of our recommended sightseeing more difficult. April to September sees a much drier period, although trade winds blow consistently on Maui throughout the year. The summer can get very hot here, with dry heat, so be prepared to take some breaks from sightseeing to cool off during this time.

If you are traveling on a budget or looking for the cheapest time to visit Maui, consider visiting in the shoulder seasons of March to May or September to early November. You’ll find accommodation prices lower at this time, as well as fewer crowds at major attractions.

If your dream is to see humpback whales, their migration takes place between January and March, and this time of the year offers you the best chance of catching a glimpse of these magnificent creatures.

Getting to Maui

Before we delve into our Maui itinerary, I have a few suggestions regarding getting to and around the island, and where to stay during your trip.

The main airport in Maui is Kahului Airport, and many of the large airlines offer non-stop flights to Maui. Alternatively, you may fly into Oahu (Honolulu International Airport) and then take a short, thirty-minute flight onto Maui. That’s what we did after our trip to Kauai and Oahu.

maui beach

There was no Wi-Fi at the airport when we landed, so be aware of that. We just walked to the closest bus stop (thanks to the offline Google Maps that I downloaded beforehand) and took a public bus.

Make sure you price-watch your flights before booking to get the best deals, using sites such as Skyscanner or Google Flights. Another great app that I like to use for tracking prices is Hopper.

Where to Stay on Maui

Maui isn’t the biggest island, coming in at 48 miles long and 26 miles wide. It would take you about one day to drive around the island, and renting a car is recommended for my itinerary below. The island is well-developed for driving. The major resort areas are in West and South Maui, with many large resorts and chain hotels to choose from.

West Maui is more developed with plenty of facilities for tourists, and the main resort areas are Kaanapali and Lahaina. There are a lot of beautiful beaches on that side of the island, great shopping areas, and restaurants.

South Maui, on the other hand, will offer you quieter beaches and has more apartment rentals. It also offers lower-budget hotel options than West Maui’s. There are still plenty of restaurants and stores in the town of Kihei, and it’s easy to walk around. From Kihei, you will need to drive about 10 minutes to the beaches for swimming.

black sand beach in Maui Hawaii

Wherever you choose to stay on the island will still offer you the opportunity to venture around and explore Maui by car. We used the Turo app to rent our car. The process of booking is very easy and straightforward.

I chose to stay in Kahului as it’s located right in the middle part of the island. So, it’s even easier to get around.

A lot of people also wonder how many days to spend in Maui?

I think five days is the perfect length of time to see the island’s highlights, but of course, you can adjust this itinerary to make the perfect Maui plan that suits you best.

Day 1 – The Scenic Road to Hana

Your first day on Maui should be spent exploring one of the world’s most famous drives, the Road to Hana.

The Hana Highway connects even the most remote areas of Maui with a twisting road that leads around the island. The drive is 44 miles in total and is a very popular activity among tourists.

My main advice is to get started as early as possible on this day, to make the most of lower crowd levels first thing in the morning. Don’t try to visit every single stop along the way as there are just too many. There are many points to see on this drive, so make sure you decide which ones are most important to you before you set off in the morning.

Another option for this day is to spend a night in Hana, but if you are not able to, it’s still an enjoyable day out. Don’t expect to tick off every landmark in one day, and just enjoy the beautiful sights on your way. Don’t expect to be able to zip along all day either, as sometimes speed restrictions are as low as 10 miles per hour, as the road is very twisted in some areas.

For this day, I recommend bringing a packed lunch and snacks with you from your hotel or a grocery store, to make sure you don’t get caught short at lunchtime if you aren’t near a good spot to stop at!

Don’t miss the Kuloa Point Loop Trail and the four-mile Pipiwai Trail, which is located after you pass Hana. They both offer stunning scenery that will take your breath away.

Other highlights on the Road to Hana are Red Sand Beach and Honomanu Bay. After a long day out, I suggest having a relaxed dinner near your hotel, and an early night to get you ready for another day of exploring tomorrow!

Day 2 – West Maui and Lahaina

Since you will probably be quite tired from the long day yesterday, we will have a more relaxed start this morning!

I recommend starting the day with a drive up to the West side of the island. If you get there in time for breakfast, you can visit the Gazebo Restaurant. I haven’t eaten there myself but heard a lot of great things about it and it has a huge list of great reviews online.

We started our day by visiting the Heart Shaped Rock on the North point of Maui.

Update: to my knowledge, the heart-shaped rock is not there anymore, as it has been destroyed by nature.

However, the ride to get there was very long and pretty scary. If you’re staying in Kahului as we did, I suggest you take what looks like a longer route and go from the South side to the West side as Google Maps suggests. We did it from what looked like a shorter route and it wasn’t the best decision. The views are spectacular but whoever is driving won’t be able to enjoy them in any way because all eyes must be on the road. The road was very narrow, and at some points, it was so narrow that if there was another car on the way, I don’t know if we would have made it. I don’t know what I would do if it wasn’t for my boyfriend driving.

Right near the Heart-Shaped Rock is located in Nakalele Blowhole. It’s worth visiting in itself as it’s pretty cool to see the geyser of seawater blowing up so high.

maui sand beach

If you enjoy snorkeling, don’t miss Napili Bay where you might be lucky enough to snorkel with Green Hawaiian Sea Turtles. Alternatively, enjoy snorkeling at Black Rock in Kaanapali, another spot where you will get to swim with tropical fish and turtles.

When you have had your fix of swimming, head to Lahaina, one of the historic towns of Hawaii.

Lahaina was the capital of Hawaii until 1845 when Honolulu took the title. It’s a touristy spot but it’s nice for a wonderful walking tour. Enjoy strolling around Front Street, and don’t miss the incredible banyan tree in the town center. The harbor area is great for a lovely stroll, and the Old Lahaina Courthouse is now a free museum where you can learn more about the history of the town.

After a busy day of exploring and swimming, head back for an early night, as tomorrow you are going to be up very early!

Day 3 – Sunrise at Haleakala

This morning is going to involve a very early start!

One of the most popular things to do in Maui is to visit the Haleakala Crater, part of Haleakala National Park. The landscape here is different from the tropical feel of Maui in general, and this dormant volcano is known as the world’s largest!

Watching the sunrise here is so popular that reservations are now required, so make sure you book your spot when reservations open seven days in advance.

Make sure you check the sunrise time during your visit (usually between 5:30 am and 7 am) and set off with plenty of time to get there. This can mean getting up as early as 3 am, depending on where you are staying on the island! Plan to arrive at the summit thirty minutes before sunrise to ensure you get a good spot. Reservations can fill up quickly, and there are only 150 car parking spots available. After sunrise, you can stay and explore the area and Visitors Center and grab a drink or snack before heading off.

If you don’t want to have a super early start, you can opt to take a daytime visit here and enjoy hiking and exploring the area.

Since we haven’t done our reservation beforehand, we went there around 1-2 pm, and the views were as spectacular. Another advantage of being there way after sunrise time is that there were almost no people at all.

Maui Haleakala National Park

It feels surreal to stand above the clouds.

The important thing to keep in mind if you decide to go there for the sunrise. Haleakala National Park is located 10,023 feet above sea level. It gets very cold and windy at the top even during the summer months. Take plenty of layers, a warm jacket with you and long pants to stay warm.

If you aren’t ready to head back to your hotel straight away, consider visiting the Kalahaku and Leleiwi overlooks, giving you spectacular roadside views of Haleakala and East Maui.

On the way back to your accommodation, you could also consider stopping at Ho’okipa Beach Park and the scenic outlook. Enjoy watching the surfers catching waves here at what is considered to be one of the top surfing beaches in all of Hawaii.

This afternoon you will probably want to just spend recovering, so make the most of your hotel and nearby beaches for some rest and relaxation time! Enjoy a nice dinner and some shopping before calling it a day.

Day 4 – Snorkel at Molokini Crater and Turtle Town

Our fourth day of your trip takes us on an incredible duo of snorkeling adventures and is one of the best activities on Maui.

Molokini Crater is believed to have been formed over a hundred thousand years ago. The clarity and quality of the water for snorkeling here are exceptional, with visibility stretching to about 100 feet. Molokini is one of only three semi-submerged volcano calderas in the whole world and is one of the must-do activities in Maui. Expect warm tropical waters and an incredible day for your whole group.

maui turtle

Located just a few miles off Maui’s shore, you will need to take an excursion to get to the crater. The crater is teeming with fish and marine animals, and you will get a chance to swim up close with them as you’ve never experienced before. Boat trips run here every day, and you can find smaller ones with a capacity of about 40 people, or larger catamaran tours for up to 150 people, depending on your preferences.

Many trips here also incorporate a stop at Turtle Town, giving you a once-in-a-lifetime chance to swim with these amazing creatures. Do note it’s against the law in Hawaii to touch turtles, but you can enjoy admiring them in their natural habitat.

Enjoy a relaxed afternoon and evening at the beach or your resort. If you are in Wailea, the places that I know are good are Monkeypod Kitchen or Ka’ana Kitchen for dinner.

Day 5 – Wailea Beaches and Luau

Your final day is dedicated to enjoying the beaches of Wailea and making the most of your last day in Maui.

If you are looking for something a little more adventurous to fill this day I suggest a helicopter ride over Maui or one of the many ziplining tours available on the island.

Wailea is one of the most touristy spots on the island, which features amazing beaches, shopping, and dining. Wailea Beach itself is perfect for sunbathing and swimming. Head a little further up the coast to Keawakapu Beach which is a more tranquil spot that is perfect for snorkeling.

More popular options include Ulua Beach, Wailea Beach, Maluaka Beach, Makena Beach, and Paako Cove.

To celebrate your last night on the island, I suggest doing something a little special. You can’t visit Hawaii without attending a Luau, and there are a couple of great options on Maui.

In Lahaina, you will find The Feast of Lele and The Old Lahaina Luau. Both of these are very popular and book up fast, so book in advance, especially if you want to get a table closer to the performance area. A Luau incorporates so many elements; music, Hawaiian dining, and incredible local food. The Feast at Lele is a popular choice as the food is brought directly to your table and there are private tables for you and your family. The Old Lahaina Luau features a buffet dinner to go with their amazing show.

black sand beach in Maui Hawaii

If you are looking for something a little more romantic, consider a Sunset Catamaran Cruise instead.

So there you have my recommendations for your perfect Maui 5-Day itinerary for a perfect vacation on this beautiful island. There is so much to explore on Maui, regardless of whether it’s your first or fifth visit. Feel free to pick and choose between days and activities to create the perfect vacation for you and your party, whether that’s an active or relaxing one.

Maui really is an island that has something for everyone and will leave you with memories to last a lifetime. If you have any questions or suggestions, feel free to leave them in the comments section below!

Scroll to Top