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5 Days in Maui | The Maui Itinerary to Follow for the Ultimate Hawaii Experience

Bonus Budgeting Tips Included

Looking for the perfect way to use up that full week of vacation time left for this year? Maybe you’ve never been to the Hawaiian Islands, or haven’t explored beyond the shores of Oahu, well read on and take notes as this itinerary lays out the perfect way to spend 5 days in Maui. 

This 5-day Maui itinerary will see you visiting the beautiful beaches, swimming with sea turtles, watching the famous sunrise in Haleakala National Park and experiencing all the other best places in between.

Is there really a best time of year to visit Maui, otherwise known as the Valley Isle? To be quite honest, by mainlander standards, the weather is only a little bit short of perfect no matter when you visit the Hawaiian Islands. However, you’re less likely to encounter rain (and large crowds) during summer months; Maui’s rainy season extends from November through to March.

Most major airlines offer direct flights to Maui’s Kahului airport. With a flight time of just over 5 hours from the West Coast of the United States, this 5-day Maui itinerary (plus 2 days of return travel) makes for the best way to use up that last remaining full week of vacation time.

With beautiful beaches around every corner, Maui is a great place to get acquainted with the Hawaiian Islands.
Rental Car While on Maui

You will want to plan for a car rental while visiting Maui. The best way to get around the island is with a set of reliable wheels. While the Valley Isle does have some public transit, it’s a good idea to arrange for a rental car ahead of time, this will ensure that you are able to get around to all the best places. Car rental prices on Maui can vary greatly, the best deals are often found ahead of time, by reserving online.

But enough about weather and transportation, let’s get into the 5 day Maui itinerary:

Day 1 Maui Itinerary: South Maui & Big Beach

Since making my first trip to Maui in 2011, I have returned to the Valley Isle several times. I always enjoy spending my first day doing the scenic drive from Kihei to Big Beach and La Perouse Bay. One of the best things about spending your first day in South Maui is that the best stops are along a 10 mile strip of accessible ocean, allowing for lots of beach time, not to mention minimal driving time after a long day of flying. Quick disclaimer: you’ll want to pack your snorkel gear for this first day of activities! So why start your trip out in South Maui? Although Kihei’s abundant condos, food trucks and golf courses are not exceptional, it serves as a central starting point. There’s a good chance that you’ll be staying close by (or maybe you’re even staying in the Kihei area). Kihei is also a good stop for picking up breakfast, coffee, or snacks to take along for your first day of adventures in South Maui (it’s always a good idea to have extra food and drinks packed, as you never know when you will want to spend extra time at some of Maui’s best beaches, coral reefs, or other popular spots). From Kihei, you will head south to enjoy your first day of Maui adventures:

Hawaiian Green Sea Turtle. Image by bphelan from Pixabay
Looking south along Big Beach, one of Maui’s best sandy beaches.

Day 2 Maui Itinerary: West Maui, Lahaina and Kaanapali Beach

Following on an adventure-filled first day road trip to South Maui, this West Maui day itinerary will bring you to more of the best beaches as well as a scenic drive along narrow roads, which promises not to disappoint.

Late afternoon Old Lahaina Luau
West Maui Nakalele blowhole
Typical narrow roads in West Maui. Image by Laurent Schmidt from Pixabay

Day 3 Maui Itinerary: Haleakala National Park Exploration and Haleakala Sunrise

Experiencing the Haleakala sunrise is definitely a once in a lifetime experience! This said, a trip to the peak of Haleakala National Park is not for the faint of heart. Here are a few considerations:

Haleakala sunrise from 10,000 feet

Would I recommend a visit to Haleakala National Park to see the sunrise with the distant ocean view? Yes, without a doubt. If you have never been to Haleakala crater, it is a must. Would I go again? No, probably not. Having experienced the Haleakala sunrise once was enough (and sans kids, making it that much easier). I would not bother taking the time to go up again, in fact, in my more recent visits to Maui, I have not ventured into Haleakala National Park (and I’m none the sadder for it).

Best stops in Upcountry Maui: Ali’i Kula Lavender Farm near Kula Lodge

Day 4 Maui Itinerary: Driving the Hana Highway

This scenic drive is hands down one of the best things you can do for a day trip on Maui. Make sure to set aside a full day for this excursion as you will have good reason to make many stops along the way.

Leave a little bit of extra time when travelling the Hana Highway to stop at one of many beautiful waterfalls.

Beautiful black sand beach; the perfect way to relax along the Hana Highway.

Now that you’ve made it to Hana, the question you’ll need to ask yourself is whether you would like to loop back, returning to central Maui via the Hana Highway (it’s interesting to experience this scenic drive in both directions), or continue along the backside of Haleakala crater and South Maui. Sections of the back road along Haleakala crater are not paved (as well as steep and not maintained). Many rental car agreements companies will forbid you from driving this stretch of road. Having driven it myself, I can tell you that it is nerve wracking, but probably the best ocean view Maui has to offer, especially at sunset.

Day 5 Maui Itinerary: Sandy beaches, return to favorite spots, relax

With so much to do on the Valley Isle, it’s always a good idea to leave some flexibility in your itinerary. Maybe you didn’t get to all of the locations mentioned previously, or perhaps you encountered rain along the way and would like to use your last day to experience a specific location in the sunshine. If you’re still looking for more new things to do, before heading back to Kahului airport for your return journey, here are a few more suggestions:

Surf lesson near Paia on Maui’s North Shore

Bonus: Best way to get the most value for your money while visiting the Hawaiian Islands

My wife and I have travelled quite frequently to the Hawaiian Islands, and so we always look for ways to get the best deals to stretch our travel budget. Here are a few tips:

5 Day Maui Itinerary: Conclusion

I’ve visited Maui over the Christmas holidays, as well as in March and April. Even though this is during the rainy season, the weather has always been very pleasant, with a little bit of rain here and there, but mostly hot sunny days. In order to have the best time possible on Maui, you need to be able to slow down and enjoy yourself.

If that means cancelling something you had previously planned on doing, it’s probably worth changing your plans for. Another option is to switch around the order of activities within this 5 day Maui itinerary, nothing is set in stone and what matters most is that you have the best time possible enjoying beautiful beaches, swimming with sea turtles and tropical fish, and taking in all that Maui has to offer.

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