If you’re planning a trip to Hawaii and wondering how to spend 5 days on Maui, you’ve come to the right place!
For fist time visitors, this epic five day Maui itinerary will take you through all of the bucket-list worthy activities around the island, ensuring you don’t miss a single highlight.
I was lucky enough to spend a month staying with family on my last visit to Maui. During that month I was able to tick off all of the must-see attractions in order to create the perfect Maui guide for you!
Whether you’re planning to spend five days or one week on the island, this detailed Maui itinerary is the ideal guideline to help you plan your time effectively. You can either follow it to a T or simply take inspiration from this guide when crafting your very own Maui itinerary.
If you have more time to spend on Maui, I’ve included some additional Maui activities at the end of this post that might interest you.
A classic Hawaiian Beach scene – Keawakapu Beach, Maui
Table of Contents
The Ultimate 5 Day Maui Itinerary – How to Spend The Best 5 Days on Maui
Where to Stay on Maui
Finding your perfect Maui accommodation may be the most important factor of the entire trip. This all comes down to two things: your budget and how you want to spend your time on the island.
Do you want to relax in the comfort of a luxury resort with a nice pool and restaurant on-site? Would you prefer to have an apartment with a full kitchen so you can prepare meals yourself? Or are you seeking a family friendly resort in Maui?
With a huge range of accommodation choices, all of these options are possible on Maui!
South Maui
South Maui has the best weather on the island which makes it awesome for soaking up the sun on the beach.
The only downside is that it’s far away from major Maui attractions like Haleakala, the Road to Hana or Maui Upcountry. This makes for a long drive every time you want to go out for the day.
Wailea – If you want the full resort experience with beautiful swimming pools, golf courses with a view and all the amenities, look no further than Wailea. This part of South Maui is home to a collection of gorgeous 5-star resorts right on the beach.
Kihei – For those seeking a laidback option near the beach, Kihei offers many condo rentals and affordable hotels. This is ideal if you’re going to be spending the majority of your time at the beach or taking day trips around the island.
There are plenty of supermarkets, shops and restaurants in Kihei which are easily accessible by foot from your hotel/condo. It’s only a 20 minute drive to Costco, Walmart, Whole Foods and other big name stores.
West Maui is a popular and bustling location to base yourself on the island. With fabulous beaches, great shopping opportunities and loads of beachfront restaurants, you can’t go wrong by choosing to stay in Lahaina or Kaanapali.
The downside to West Maui is that it can get quite busy, especially during high season. If you’re not a fan of crowds filling up the streets, then you’d be better suited in Kihei or Wailea.
Lahaina & Kaanapali – The historic whaling village of Lahaina has a lively atmosphere with busy streets, popular restaurants and easy access to whale watching and snorkeling boat trips.
The resort community of Kaanapali is a 10 minute drive up the road from Lahaina and offers a wide variety of great accommodation choices. Ranging from budget friendly motels to fancy beachfront resorts, you’re guaranteed to find what you’re looking for in West Maui.
Staying in this part of the island is a less popular option but it puts you closer to Haleakala and the Road to Hana, significantly cutting down your driving time to both attractions.
You may choose to stay in this area for a night or two to make sightseeing on this part of the island more convenient. For those looking to get off the beaten path in Maui, you’ll find some unique accommodation choices.
Paia & Kula – Set along the slopes of Haleakala, you’ll get a spectacular view over west and south Maui from Kula. Staying in the small town of Paia will allow easy access to the less touristy north shore beaches and give you a head start to driving the Road to Hana.
East Maui receives a lot more rain than other parts the island. Aside from exploring the Road to Hana, there really isn’t much more to do here. It’s also a very long drive to get anywhere else on the island which means most people choose to stay in East Maui for only a few nights.
Hana – Break up your drive on the Road to Hana by spending one night at a hotel/apartment in Hana.
The spectacular Red Sand Beach near the town of Hana
Where to Rent a Car on Maui
If you’re planning to follow this Maui itinerary pretty closely, renting a car is the only option (unless you plan to book individual tours/day trips). Maui is a big island and the main attractions are quite spread out.
Want to drive the Road to Hana or watch the sunset on Haleakala? These are two essential Maui activities where public transportation isn’t an option. Trust me, you’ll have way more freedom and convenience by having a car during your 5 days in Maui.
When it comes to renting a car on Maui, the best place to do so is on arrival at the Kahului Airport. Check out this website to browse car rental options and book your rental car online before you arrive.
**Tip** If you’re renting a car, the cheapest places to buy gas on Maui is at Costco or Safeway. Save yourself some money by fuelling up at either gas station before driving the Road to Hana or making your way to the summit of Haleakala.
If you’re visiting Maui from overseas, then you’ll need to get travel insurance before you go.
Travelling to any country without insurance is not worth the risk. The reality of travelling overseas is that unexpected things can happen at anytime so the best thing you can do is be prepared.
For peace of mind while abroad, Heymondo is one of the most reputable travel insurance companies that will provide you with simple and flexible coverage. Whether you are into adventurous activities or simply looking for trip cancellation and medical insurance, Heymondo has you covered.
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While Maui is a great holiday destination with warm temperatures year-round, you may want to plan your trip according to the following seasons.
October – April (Winter): If you’re looking to escape the freezing cold winter on the mainland (like most people) then this is a great time to visit Maui. The island sees more rain during this time of year however the weather changes quickly and rain showers usually don’t last longer than an hour.
There is a chance that you might get unlucky with storms lasting several days to a whole week. This is unfortunately down to luck and there is no way to predict what the weather will be like when you visit Maui during the winter months.
Since Maui has a tropical climate, the temperatures during winter hover between 20 – 30°C (mid 70’s – low 80’s °F). When I spent a month on Maui from the end of January to the end of February, it rained a fair amount but I also had plenty of warm and sunny beach days.
May – September (Summer): The summer months are also a great time of year to visit Maui with less rain, warm temperatures and ideal sightseeing weather. This time of year coincides with summer vacation making it a popular time for family holidays when the kids are off school.
April/May or September/October (Low Season): For lower accommodation prices and less crowds “low season” or spring/fall is the perfect time to plan your 5 days on Maui if you’re on a budget.
December – April (Whale watching season): This is the best time to spot humpback whales as they migrate down from Alaska to the warm waters of Hawaii to breed. Book a whale watching tour anytime during these months to see them breaching and playing at the ocean’s surface.
Enjoying a beautiful sunset at Palauea Beach
What to Pack for 5 Days on Maui
Here is a general packing list for some of the important must-haves when visiting Maui. If you forget to pack something, don’t worry. Maui has all the usual shops like Walmart, Costco, Target etc. so you’ll be able to find everything you need on the island.
Day pack – When taking day trips or doing any hikes, you’ll need a good backpack to fit your essentials in.
Reef safe sunscreen – This is something you’ll need for any ocean related activities (swimming, snorkeling, surfing etc). The chemicals from regular sunscreen wash off your skin in the water which can harm marine life. As of October 1, 2022, the County of Maui has banned the use of non-mineral sunscreen in order to protect the coral reefs and the sea animals who inhabit them.
Aloe Vera Gel – If your skin hasn’t seen the sun for a while you may be prone to getting sun burnt, always have some aloe on hand just in case!
Waterproof phone case – I ordered this waterproof phone case from Amazon and was so glad to have it on the whale watching tour and snorkeling day trip. This is especially good for the small-raft boat tour as you’ll be sitting low and will likely get splashed a few times by waves.
Fast drying beach towel – Most hotels will give you beach towels but I love my microfibre towel which dries super quickly and keeps the sand off easily. It is compact (easy to fit in your luggage) and perfect for day trips, think waterfall hopping on the Road to Hana or snorkeling boat tours.
Rain jacket – Rain is unpredictable on Maui and sometimes the weather is completely different from one side of the island to the other! It may be sunny when you depart from Kihei in the morning only to find storms and rain in Hana by the afternoon. Always come prepared with a rain jacket in your day pack.
Warm jacket – Bringing a warm jacket to Hawaii may seem strange until you’re standing at the top of Haleakala volcano and it’s freezing cold! Trust me, it is 100% necessary if you’re planning to watch the sunrise or sunset up there. Due to the high altitude, the temperature is always significantly lower than the rest of the island.
A warm jacket came in very handy during my sunset trip to the summit of Haleakala
Flip flops– You’ll be living in these on your trip to Maui so be sure to bring your comfiest pair. Or just buy some new ones when you get there!
Hiking boots – If you’re thinking of doing any hiking on Maui, whether it be on Haleakala or the Road to Hana, don’t forget to bring a pair of sturdy hiking boots.
Sunglasses– Pack a pair of polarized sunglasses to keep your eyes protected from the harsh UV rays.
Sun hat – Protect your head from the sun while looking cute at the same time with one of these foldable sun hats.
Beach bag– Your 5 day Maui itinerary is likely to include plenty of beach time, don’t forget to bring a beach bag.
Camera– You’ll need a good camera (or phone camera) to capture all of the magical moments and memories that your 5 days on Maui will bring!
Portable phone charger – Always keep one of these handy in your bag when you’re on the go.
Mask & snorkel – If you book a snorkeling tour, this will be provided. If you’re planning to spend a lot of time snorkeling from the beach, having your own set is a must.
Motion sickness tablets – For those who are easily affected by rough waves on boat excursions or winding roads (Road to Hana/Haleakala Highway), you’ll need to have this on hand.
Sweeping coastal views on the back Road to Hana
5 Days in Maui Itinerary – Overview
Day 1 – Plan to do a half-day snorkeling boat trip to Molokini Crater and Turtle Town.
Day 2 – Spend a relaxed morning at a beach of your choice followed by a sunset mission to the summit of Haleakala.
Day 3 – Start the morning with a whale watching boat cruise that departs from Lahaina Harbor followed by some sightseeing and shopping in the town of Lahaina. Have lunch and then hit the beach for the afternoon. Finish off the day with a delicious feast at a traditional Hawaiian Luau.
Day 4 – Wake up early to spend the full day exploring the highlights of the Road to Hana. You can either do the drive yourself or book an organized Road to Hana day trip which includes hotel pick up/drop off.
Day 5 – Spend the day visiting the attractions around Maui’s Upcountry such as MauiWine, Ali’i Kula Lavender Farm, Paia, and Ho’okipa Beach. Enjoy an amazing final dinner at the iconic Mama’s Fish House or Paia Fish Market.
