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Maui 5 Day Itinerary

Welcome to Maui, the ultimate tropical paradise! This beautiful island boasts an abundance of stunning beaches, lush rainforests, and breathtaking scenic views. In this 5 day Maui itinerary, you will have the opportunity to experience the best of Maui’s natural wonders, cultural heritage, and adventure activities.

Whether you’re seeking relaxation or excitement, you’re sure to find it in Maui. Maui is the perfect destination for honeymoons and families alike. I would know I specialize in both Hawaii honeymoons and Hawaii family and group trips! 

Maui is a great mix of beautiful nature, plus plenty of activities and restaurants. It’s the perfect mixture between the hustle and bustle of Oahu and the beauty of Kauai, offering the best of both worlds. Plus, Maui is the only island where you can visit another island (Lanai) by ferry. 

Yes, Maui is OPEN after the devastating wildfires in the summer of 2023! Please consider visiting Maui to help local businesses recover from the loss of tourism! The areas popular for tourism were largely unaffected, and most of the popular activities (Road to Hana, Haleakala, Wailea, etc., are fully open and operational.) Maui needs our help! 

Do I need a rental car in Maui?

YES! I strongly recommend renting a car in Maui. You truly need one as public transportation is not reliable, and you’ll want to fully explore the beautiful island. You’ll find the best prices anywhere at Discount Hawaii Car Rental. You can reserve a car not, and only pay when you pick it up. 

Day 1

You’ll start day one in Maui early in the morning. Since most flights arrive in Maui in the late afternoon, I don’t count your arrival day as your first day.

On your first day, you’ll likely check into your hotel, get some dinner, and call it an early night. Depending on where you live, 8 PM in Hawaii will likely be midnight or later for you!

Heading to bed early can help you recover from jet lag after your long flight. You’ll likely wake up very early due to the time difference. I have more tips on avoiding jetlag here: How to survive the flight to Hawaii & how to fight jet lag in Hawaii.

You have two options for the very first day of your 5 day Maui itinerary.

Option 1 – a slow start

First, you can get a slow start. This is the perfect day to explore Ka’anapali Beach on the west shore of Maui. 

On Kaanapali Beach, you can go snorkeling at Black Rock. If you don’t want to snorkel on your own, I highly recommend snorkeling at Molokini Crater. This is my #1 recommendation for things to do in Maui. I recommend sailing on the Four Winds II. 

No matter which option you choose, snorkeling is an excellent way to see tropical fish and other marine life. 

You may also want to spend part of your day at Whaler’s Village. This busy village is full of shops and restaurants. If you plan on doing any shopping, I recommend arriving early. The stores get crowded quickly.

Restaurants in Ka’anapali 

Some of the best restaurants in Ka’anapali can be found in Whaler’s Village too. It is best to make reservations to ensure you don’t need to wait long for a table.

There are a couple of golf courses nearby. So, if someone is a golfer, they can head out to play a round or two while everyone else has their beach day. Check out The 15 best golf courses in Maui to learn more. 

When you are finished at Kaanapali Beach, head over to Honolua Bay. The bay is about a 15-minute drive from the beach. It won’t take much time at all to get there.

After a long first day of beach time, you will be more than ready to head back to your resort. You may want to go to bed early so you are ready for the pre-dawn wake-up call on your second-day itinerary.

A more lively start

If you opt to do a helicopter tour in Maui, I recommend doing it on the morning of your first day. Helicopter tours can often be rescheduled due to weather, so it’s best to schedule the helicopter tour early in your trip. I recommend a tour that includes West Maui and Molokai or a helicopter tour to Hana if you don’t plan to drive it. 

If you happen to visit Maui during whale-watching season, head out on a catamaran cruise. Those cruises are the best way to see humpback whales. Although if you’re staying on the west side of Maui, you’ll often spot them on your own lanai.

Day 2

On your second day in Maui, I recommend getting up early to watch the sunrise from the Haleakala Crater. This crater is within Haleakala National Park.

The best place to watch the Haleakala sunrise is from the summit. That means driving 38 miles on the winding road that leads to the summit. In the dark. In a car rental.

The sun rises between 5:30 and 7:00 in the morning. The long drive can take extra time due to the darkness. And you should arrive at least 30 minutes before sunrise. This is to beat the crowds and find the perfect viewing spot.

I can always schedule a guided tour for this experience on Maui. This is a good idea if you don’t want to drive in an unfamiliar area in the early hours of the morning!

No matter what, don’t skip this unique experience. After all, the summit is the perfect spot for watching the sun rise over the island! You can also take a tour where you bike (downhill) afterward; it’s always a huge fit with my clients! 

Oh, and dress warm when you leave your resort. It’s cold up at the summit!

Visit South Maui

Once the sun has risen, you will have the remainder of the day to spend in South Maui.

You may want to head out on the water during a kayak tour. This is one of the best ways to see the green sea turtles during your Maui vacation. When you are out on the water, look out towards Molokini. It is a small islet that is considered the absolute best snorkeling area in Maui.

The afternoon can be spent at the Shops at Wailea. This is one of the favorite shopping centers on the island. You will have the best time purchasing souvenirs! Check out the 25 best restaurants in Wailea Maui to figure out the best place for dinner. 

In between shopping adventures, you can participate in one of the Hawaiian cultural activities that take place in this area. One of the best things to do is learn how to make a lei.

Since you’re in Wailea, I recommend one of my favorite luaus for dinner. Keep in mind you’ll want to reserve these far in advance. I recommend the Maui Nui Luau at the Sheraton Maui or Te Au Moana Luau.

Day 3

Day 3 should be an easy day for you since day four will be packed full of different experiences.

You can choose to visit Kapalua Bay Beach. This is one of the best beaches on West Maui. The parking lot for this sandy beach is small. So, it is best to arrive early if you want to find a spot to park.

If you are interested in Hawaiian history, you can head into central Maui. That is where Iao Valley State Park is located. The battle of Kepaniwai was fought in this location in 1790. 

Within the Iao Valley, you can walk through the rainforest. Or check out the interactive exhibits at the Hawaii Nature Center. It would also be a good day for a hike! Check out the best hikes in Maui to find the perfect hike for you. 

Day 4

Day 4 of your Maui vacation will be spent along the north shore. This is where the Hana Highway is located.

You must get an early start for this long drive. The Road to Hana, or Highway 36, is 52 miles long. It is a scenic drive with narrow roads and sharp curves. Driving this route is the best way to see numerous sights within a single day.

Before you head out, you should understand there are more than 40 stops along this highway. So, while you can drive 52 miles in 3 hours, it usually doesn’t happen unless you don’t make any stops.

However, it’s crazy not to stop! Who would possibly want to skip the beauty along the Road to Hana and make the drive? If you are trying to see as much as possible during your 5-day itinerary of Maui, you will want to see the best stops at least.

The best stops on the Road to Hana

So, let me share the best stops along the Road to Hana:

• Twin Falls at Mile Marker 2
• Ho’okipa Lookout at Mile Marker 9
• Hana Lava Tubes at Mile Marker 31
• Wai’anapanapa Black Sand Beach at Mile Marker 32 – This is also where Wai’anapanapa State Park is located
• Lindbergh’s Grave at Mile Marker 41
• Ohe’o Gulch or the Seven Sacred Pools with the Pipiwai Trail at Mile Marker 42

I also have a blog post with a guide to the Road to Hana that you can check out for more information. 

After the Road to Hana

Try to schedule your time near Paia Town for lunch or dinner. Just past the town is a restaurant called Mama’s Fish House. It is a great place to grab a bite to eat and relive the memories of the day. However, you’ll need a reservation, and they book out almost six months in advance!

The Hana Highway is an amazing day trip everyone should take when on vacation in Maui. While you can do the drive yourself, you can also go on a guided tour. This is a great option if you know you don’t want to tackle this slightly dangerous road on your own.

If you do make the drive by yourself, determine where all your stops will be on Google Maps. This will make it easier as you are trying to navigate the winding road.

Day 5

Day 5 will be your last day in Maui. All good things must eventually come to an end. Thankfully, most direct flights to the mainland leave later in the day. This means you will have plenty of time to see a few more sights.

I like leaving the final day open with some options. You can visit the Maui Nui Botanical Gardens. That is a calm adventure filled with colorful beauty.

Or you can get more beach time at Maluaka Beach. This is one of the sandy beaches where Hawaiian green sea turtles spend their time. The locals call the beach Turtle Town, thanks to all the turtles living there.

This beach is the perfect place to snorkel on your last day in Maui. The coral reefs are delicate but surrounded by marine life. I recommend visiting this area with a guide so that you can get there by the water. Arriving by land doesn’t offer easy access to Turtle Town. Maui Kayaks has been a favorite for myself and my clients!

Keep an eye on the time during any activities you do on your last day in Maui. It will be time to head to Kahului Airport before you know it.

Do you need even more ideas? Check out 50 things to do in Maui.

Pro tip from a Hawaii Travel Agent: Ask your resort to hold your luggage. I do not recommend driving around with your stuff in your rental car. Although Hawaii has relatively low crime, thieves do target rental cars. Better safe than sorry! 

5 day Maui itinerary

I hope this Maui 5 day itinerary itinerary helped you plan your Maui vacation. I also have a 7-day Maui Itinerary and a 4-day Maui Itinerary if you need to plan a longer or shorter Maui vacation. 

Things to do in Maui

As a Hawaii Travel agent, I book Maui more than any other island! If you want more ideas for your Maui 5 day itinerary, I have plenty of Maui travel tips on the blog, including: 

• The Best Beaches West Maui
• Black Sand Beaches Maui
• 15 easy hikes in Maui
• Things to do in Lanai (you can take the ferry from Maui!) 
• The 15 best resorts in Maui for families

Guess what? I am a Hawaii Travel Agent, and I love planning vacations and honeymoons in Maui! You can contact me if you’d like more information. I recommend starting with my Hawaii travel guide if you plan to DIY your vacation!

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