Maui Itinerary: How to Experience The Best of Maui in 5 Days!

Ready for the ultimate tropical escape? Maui Hawaii is the perfect island for those looking to break away from their daily routines and enjoy a little fun and sun. Now we know what you might be thinking… But that this isn’t your typical Maui itinerary! Our 5 day Maui itinerary is full of beach hopping, hiking, and all the Hawaii adventure you can handle!  

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Maui Travel Tips 

• 10 Best Beaches in Maui to See on Your First Visit
• Huli Huli Chicken to Pineapple Wine: Best Maui Food & Drinks
• 20 Fun Facts About Maui Hawaii to Know Before You Go
• How to Find the Best Airbnb: 8 Tips We Always Use
• Packing For A Day Hike: 10 Essentials We Always Carry 

Planning Your Maui Itinerary

Maui is a beautiful island for a vacation or even to include as part of a larger Hawaii trip. We spent over two weeks exploring and STILL didn’t see all that Maui has to offer.

The good thing is it doesn’t matter if you have a 2 day, 5 day Maui itinerary or even more! There is truly something for everyone in Hawaii. Check out our full travel planning guide for Maui below. It is designed to help you plan your trip to the island in just 10 easy steps.

→ Planning a Trip to Maui: 10 Step Easy to Follow Travel Guide

→ Where to Stay in Maui Hawaii: 4 Best Areas With Awesome Hotels

Renting a Car on Maui

Something you should know when planning your trip to Maui is that it’s a pretty big island! That means many of the best beaches and activities are spread out. Unless your 5 day Maui itinerary will be simply lounging at your hotel, you’ll need a car!

The best way to do this is to pick one up directly from the airport. We used Discover Cars to book ours and paid $550 for two weeks which is very cheap for Maui. We also paid just over $100 each way for direct flights from California on Hawaiian Airlines!

You’ll want to confirm as far in advance as possible especially if you’re traveling in peak season. A rental car is typically a big expense for your Maui itinerary, but we promise it’s worth it for what you’ll see!

→ 6 Things to Know Before Renting a Car on Maui Hawaii

→ Hawaiian Airlines Review: Is it the Best Airline to Fly to Hawaii?

Maui Itinerary Day 1: Arriving in Maui Hawaii

When traveling to Maui try to book a flight that lands in the morning or as early as possible. That way you’re able to fully enjoy your first day. We arrived around 1pm on a flight from San Diego California. 

While there are many great places to stay we highly recommend basing your adventures in Kihei. There are amazing hotels, great restaurants, and so much to do in the area.

After checking in the first thing you should do is hit the beach! If you’re staying in Kihei as we did head right to the ocean. Stroll along the Wailea Beach Walk which takes you along multiple stunning beaches.

The walk goes right by the Andaz Maui Resort, Four Seasons Resort Maui, and Fairmont Kea Lani. If you are staying at one of these properties that’s even better! 

Maui Itinerary Tip: Not staying on this part of the island? Use this time in your itinerary for Maui Hawaii to see your own area! 

Maui Itinerary Day 2: Driving the Road to Hana

On day 2 you’ll be waking up excited to see the island. So you might as well take on one of the most popular activities! Driving the Road to Hana is a day of twists, turns, hiking, and lots of roadside snacks. You should plan for a full day experience, starting the drive at sunrise and returning to your hotel late in the afternoon. 

→ Best Road to Hana Stops: One Day Maui Guide With Route & Waterfalls

The Road to Hana was one of our favorite days in Maui, but we did do it a little differently than most! Instead of stopping along the way, we made the drive to the end of the route to be one of the first people on the Pipiwai Trail.

This famous bamboo forest and waterfall hike will be one of the highlights of your 5 day Maui Itinerary. After experiencing the 400 ft Waimoku Falls, we took our time on the way back stopping at more waterfalls and scenic viewpoints. Make sure to check out our guides before taking on the Road to Hana!

→ 10 Road to Hana Tips to Know Before Taking Maui’s Most Famous Drive

Maui Itinerary Day 3: Lahaina & West Maui

On the third day of your itinerary for Maui Hawaii, we’re jumping right back in the rental car! It’s time to take an epic drive out to West Maui. Assuming you’re staying in the Kihei or somewhere else on the island, you’ll have an incredible coastal drive with sweeping views of the ocean.

There is so much to see and do along this route! You can snorkel at Honokohau Bay, walk the Kapalua Coastal Trail, and visit the local farmers markets. Also, save at least a few hours for the cute town center of Lahaina to grab lunch. 

Staying in Lahaina?: If you are already in that area of the island then simply do the drive in reverse. Head to Kihei, stop at Ululani’s Hawaiian Shaved Ice, and check out the Wailea Beach Walk!

Maui Itinerary Day 4: Haleakalā National Park

A visit to Haleakalā National Park is not to be missed on your 5 day Maui Itinerary! Although the massive Haleakalā volcano is visible from all over the island, it’s actually quite far from most places to stay. 

In fact, from Kihei it took about an hour and a half just to drive to the top. Also, we left the warm 87 degree weather behind at the beach. It was under 60 on the top of Haleakalā!

Make sure to bring extra layers especially if you are going early in the morning. There are a few different ways to enjoy the park which we break down below.

Maui Sunrise Mission

Watching the sunrise from the top of the island is one of the most popular activities in Maui. Tickets can be hard to come by and often need to be booked on the National Park Website weeks (if not months) in advance! Pre-order your tickets and drive yourself, or take a sunrise group tour.

Hit the Trails

Haleakalā National Park also has some of the most unique scenery we’ve ever seen. Sliding Sands is a wild hike and one of the best trails on Maui. It’s quite long and a good degree of fitness is required. However, you can also just walk 30 minutes to an hour into the crater before turning around.

After visiting Haleakalā National Park it’s best to make the most out of your time exploring this part of the island. In the area known as upcountry, you can also include the MauiWine and the botanical gardens into your 5 days in Maui itinerary.

Maui Itinerary Day 5: Beach Day w/Goat Walk 

For your final day, it’s time to mix adventure with relaxation. In the morning take a drive out to the Maui Lava fields where you can hike the Hoapili Trail! This path is more of a long walk than a steep hike. It will give you a special look at this side of the volcanic island.

Afterward, head down the road to Mākena State Park. This long sandy beach has fun waves and crystal clear water. Pack a lunch or stop at Jazzy’s food truck for tacos across the street from the entrance.

If you’re looking for a more something more extreme then plan to hike Waihee Ridge Trail. This is the most difficult hike on our itinerary for Maui Hawaii, but the views were spectacular!

Ending Your 5 Days in Maui Itinerary

After almost a week in Maui you’ll surely be exhausted, but happy to have seen so much of this amazing island. If you have extra days to explore there are plenty of adventures to be had. Check out our post below for more of the best things to do and see!

→ 25 Fun Things to do in Maui Hawaii for Every Type of Traveler

Have any questions about our 5 day Maui itinerary or want to share your favorite island activities? Let us know in the comments below! 

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar! 

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Where to Stay in Maui Hawaii

Ultra Luxury – Four Seasons Resort Maui – Wailea – Known as one of the most elite hotels on Maui, the Four Seasons has three swimming pools, 5-star service, and is just steps from the beach. 

Fun Vacation – Andaz Maui at Wailea Resort – Wailea – This modern, upscale hotel is packed with swimming pools and ocean views. 

Bed & Breakfast –Maui What a Wonderful World Bed & Breakfast – Wailea – Get all the local charm you can handle at this unique bed and breakfast. Awesome location that will provide a homey welcome to the island. 

Aparthotel – Napili Sunset Beach Front Resort – Lahaina – Great for travelers looking to have a little more space and a kitchen.

Hostel Life – Hakuna Matata Maui Hostel –  Lahaina – Walking distance to the town center, this hostel is set in a beautiful garden. Hakuna Matata also offers free bikes and is close to the beach.

Remote Resort – Hana Maui Resort A Destination by Hyatt – Hana – Located in the far remote part of the island along the road to Hana. Amazing resort by Hyatt offering seclusion and luxury. 

For more places to stay in Maui you can explore the latest prices here!

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Hawaii Travel Planning 

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials! 

 Flights: We always find our cheap flight deals using Skyscanner. That’s how we got our flight from San Diego to Maui for under $100 USD on Hawaiian Airlines!

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also,  Hostelworld should be your go-to source if you’re traveling on a budget. 

 Rental Car: Hands down the best way to explore Maui Hawaii is with a rental car! We used Discover Cars to explore the island. Just make sure to book in advance because there are limited cars on the island in the high season! 

 Tours: Check out Get Your Guide to find hundreds of Maui activities. You can book a sunset sail from Lahaina, Road to Hana full day tour, or go wild and take a rainforest helicopter tour! 

 Travel Insurance: Never travel abroad (if you’re traveling to Hawaii from outside the USA) without protection. We’ve been using SafetyWing for the last few years on the road and they are there when we need them.

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