An Adventure-Packed 5 Day Maui Itinerary

An Adventure-Packed 5 Day Maui Itinerary

Maui brings epic sunrises, lush rainforests, rich history, and tons of adventure. Use this 5 day Maui itinerary to plan your perfect trip!
Surfing in Maui - Rachel Off Duty

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Rachel Off Duty: 5 Days of Adventures on Maui

I was hosted by the Maui Visitors & Convention Bureau for part of my most recent visit to Maui. All thoughts and opinions are my own.

Maui is one Hawaiian island that I just can’t seem to get enough of. I have such fond memories of adventures on Maui with my family as a kid, and even though I was raised on Oahu, I’d often claim Maui was my favorite island. 

In many ways, it still is. But as I’ve grown up I’ve found so many things I love about Oahu, the Big Island, and Kaua’i too that it’s impossible, and unfair, to choose a favorite!

Maybe it’s the 80+ multi-colored beaches, the 10,000+ foot summit of Haleakala, or the dense green rainforest near Hana. Or, maybe it’s the fact that even though there’s a lot of different places to explore and fun things to do on Maui, the island doesn’t feel overwhelming or overly done. Whatever it is, Maui is an island I love returning to over and over again. 

If you’re planning a Maui adventure and wondering what to do, read on for my 5 day Maui itinerary. I break down my favorite way to spend 5 days in Maui, where you’ll get a taste of everything I mentioned above and more. And, at the bottom of this post, you’ll find easy ways to extend your trip if you have more time, plus my recommendations on where to stay, what to eat, and what to know before you go! 

P.S. Already have your Maui itinerary, and just looking for some more things to do? Don’t miss my guide to Things to Do on Maui!

RELATED: How to Plan a Trip to Hawaii – Everything You Need to Know

An Adventure-Packed 5 Day Maui Itinerary

DAY ONE: Lahaina and Ka’anapali

Rachel Off Duty: How to Spend 5 Days on Maui

If you’re flying to Maui from the mainland (AKA the continental USA), the Maui airport is located in the city of Kahului. This itinerary assumes you’re staying in west Maui in the town of Lahaina when you first arrive (a 40 minute drive from the airport). But, if you’re staying in Kihei or Wailea (a 20-30 minute drive), you can easily swap days one and five of this 5 day Maui itinerary!

On day one of your 5 day Maui itinerary, I recommend kicking things off by cruising around west Maui. Here, you’ll find beautiful beaches and snorkeling opportunities. From there, you’ll end your day exploring the famous and historically significant town of Lahaina. 

Let’s get into it!

West Maui Beaches

Rachel Off Duty: 5 Days of Adventures on Maui - West Maui Beaches
Rachel Off Duty: How to Spend 5 Days on Maui - West Maui Beaches

On your way to the beach, stop at Leoda’s Pie Shop in Olowalu (bacon and egg sandwiches), or Drift Coffee in Lahaina (tastiest iced coffee), to fuel up for your first day! A block down the road from Drift Coffee, you’ll also find a little food truck area with some tasty breakfast bites. Baya Bowls and TaquerEATa were my personal favorites. 

Rachel Off Duty: 5 Days of Adventures on Maui - Breakfast at Leoda's

Once you’re fueled up and ready, hop in the car and head further west for a beach day!

West Maui is home to several beautiful beaches in quick succession, starting in Olowalu. So, you won’t have a hard time picking a Maui beach to enjoy! Pick one or two and spend your day snorkeling, sunbathing, or swimming before heading back to Lahaina for dinner. Look closely – you should have good views of the Hawaiian islands of Moloka’i and Lana’i in the distance!

Some West Maui Beaches To Visit:

  • Olowalu 
  • Kaanapali Beach
  • Kahekili Beach Park
  • Honokowai Beach Park
  • Napili Bay 
  • Oneloa Beach
  • DT Fleming Beach Park
  • Honolua Bay
  • Slaughterhouse Beach

PRO TIP: If you can’t bring yourself to leave, grab dinner close to the beach at The Plantation House or the Honoapiilani Food Truck Park instead of heading back to Lahaina.

Lahaina Town

Rachel Off Duty: 5 Days of Adventures on Maui - The Lahaina Banyan

The beachfront town of Lahaina is one of the most highly visited areas in Maui. Lahaina has a long history of significance in Hawaii, and was even briefly the capital of the Kingdom of Hawaii before it moved to Oahu. In this small town, you’ll find tons of restaurants, bars, landmarks, and a bustling harbor with beautiful sunsets.

Window shop your way down Front Street – voted one of the greatest streets in the USA – and take in the energy of this lively town. Be sure to admire the massive Lahaina Banyan (it’s as big as an entire city block) before heading to an early dinner or post-sunset drinks!

DAY TWO: Haleakala National Park and Upcountry Maui

Rachel Off Duty: 5 Days of Adventures on Maui - Haleakala National Park

Day two of your adventures on Maui starts with a suuuuper early wake-up call. You’re going to catch one of the most staggeringly beautiful sunsets at the top of the world today! 

Haleakala National Park – Summit District

Rachel Off Duty: 5 Days of Adventures on Maui - Haleakala National Park Sunrise
Rachel Off Duty: 5 Days of Adventures on Maui - Haleakala National Park Sunrise
Rachel Off Duty: 5 Days of Adventures on Maui - Haleakala National Park Sunrise

One of two national parks in Hawaii, Haleakala is a must-visit during your Maui trip.

Meaning “House of the Sun,” Haleakala has been a place of cultural and spiritual significance for Hawaiians for centuries. The site of this national park is named from the exploits of the demi-god Maui (have you seen Moana?), and is still used today for sacred rituals, including reserved areas dedicated to the burial of the dead. If you go for sunrise, you may even hear locals lead daily ritual chanting to greet the sun. You are encouraged to participate! 

Speaking of sunrise, Haleakala National Park is world-famous for its sunrises (they’re pretty spectacular). Because of this, you’ll want to make a reservation using this link ahead of time and plan to leave your hotel no later than 3:30 am to make it up the mountain before the sun begins to peek. Be sure to bundle up, as temperatures can often drop 20-30+ degrees below what you’ll find at sea level. 

Alternatively, sunset at the 10,023 foot summit of Haleakala is just as beautiful and usually much less crowded.

While in the Summit District of the national park, be sure to explore some Haleakala hiking trails, like the short Leleiwi Overlook, or the longer Keonehe’he’e and Halemau’u Trails.

Camping at Haleakala National Park

Rachel Off Duty: Camping at Haleakala National Park

Want front-row seats to the world-famous Haleakala sunrise? Try to cinch a campsite at Hosmer Grove Campground, just 20-30 minutes from the summit. You’ll want to look for reservations several months in advance as there are only 6 campsites. But, if you can find an open spot, you’ll be rewarded with incredible stargazing by night, and easy access to an unforgettable sunrise.

PRO TIP: If you do get a campsite reservation, you do NOT need to make a separate sunrise reservation for Haleakala! It’s included!

Upcountry Maui: Kula and Makawao

Rachel Off Duty: Upcountry Maui

After your morning in Haleakala (or, before you go for sunset), grab a bite in upcountry Maui at Kula Bistro, and wander around the paniolo (Hawaiian cowboy) town of Makawao. 

With cowboy heritage and modern-day boutiques and art galleries, Makawao is one of those off-the-beaten-path Maui gems you wouldn’t expect. Wander around the little downtown area and pick up a souvenir or two!

DAY THREE: Water Activities and ‘Iao Valley

Rachel Off Duty: Water Activities on Maui

Since you spent yesterday exploring the highest summit in Maui, start day three of your 5 day Maui itinerary at sea level by getting out on the water! Then, explore west Maui’s ‘Iao Valley for some Hawaii history and epic views. 

Water Activities in Maui

Like any Hawaiian island, one of the most popular thing for visitors to do is enjoy the warm water and tropical weather. While you can lie on the sand and relax, for a more active experience, try one of these water adventures on Maui. 

  • Go Surfing: Take a surfing lesson at Ukumehame Beach Park with woman-owned Maui Surfer Girls. You’ll be standing up before the end of the two-hour class! If I can, so can you!
  • Go Snorkeling: Maui is home to some astounding underwater ecosystems. Two impressive Maui snorkel sites are the Coral Gardens and Molokini Crater, accessible only by boat with tours like this.
  • Take a Catamaran: For a more leisurely experience, take a catamaran sail. The snorkeling is optional but the drinks are all-included!  
  • Go Whale Watching: Whale watching season in the Hawaiian islands typically peaks from December to February. See whales on Maui with a kayaking tour or a 2-hour catamaran tour, where there’s a good chance you’ll spot dolphins or sea turtles, too.

‘Iao Valley

Depending on what time you’re back on land, and how much energy you have, I highly recommend exploring a bit of ‘Iao Valley. This state park is the site of the 1790 Battle of Kepaniwai, where King Kamehameha I fought Maui’s army in a battle to unite the Hawaiian islands. 

If you have less time, visit the ‘Iao Needle State Monument, which takes just 10 minutes to walk to on a well-marked pedestrian trail. This ‘needle’ (more like a pointy hill) served as a lookout point during the battle that would ultimately be a turning point in Hawaiian history. 

If you have more time, I also recommend spending around 2-3 hours hiking the Waihe’e Ridge Trail. This 4-mile trail will wear you out, but you’ll quickly be rewarded with a waterfall and 360-degree views of the West Maui Forest Reserve and the Pacific Ocean.

Depending on the weather and time of day, you’ll either have clear views at the top, or find yourself walking amongst the clouds!

PRO TIP: On your way to ‘Iao Valley, fuel up (and window shop) in the town of Wailuku!

Rachel Off Duty: 5 Days in Maui - 'Iao Valley Needle

DAY FOUR: Pa’ia and the Road to Hana

Rachel Off Duty: 5 Days in Maui - Pa'ia Town

One of the most famous Maui adventures you can have on your 5 day Maui itinerary is exploring the Road to Hana. Today, you’ll explore Maui’s north shore and east side, starting early (between 6 and 8 am, if you can!) to beat the crowds and maximize your time to enjoy. 

The Road to Hana

Rachel Off Duty: 5 Day Maui Itinerary – Road to Hana

Contrary to its name, the road to Hana road trip is less about Hana, and more about the journey to get there. This 3-hour-one-way road trip wiggles along the north shore of Maui, weaving past beautiful multi-colored beaches, darting around waterfalls, and brushing through small towns. 

RELATED: How to Plan a Trip to Hawaii – Everything You Need to Know

A couple things to know about the Road to Hana if you go: 

  • This is a very popular Maui adventure, with hundreds if not thousands of rental cars cruising along the Hana Highway on any given day. Starting as early as possible in the morning will help alleviate some of the traffic you’ll experience along the way. 
  • Most people plan the road to Hana as a one-day activity, like you’ll see in this guide. However, it’s actually better if you can manage to spend the night on the north shore or east coast of the island. That way, you can explore at a more leisurely pace. Consider spending a night of your Maui Itinerary in one of these hotels, if you can:
  • Be patient and practice aloha when driving, and please drive attentively! The road is windy and in some places, narrows into a one-lane path. 
  • Because of the road to Hana’s popularity, it’s become a bit of an overwhelming strain on local residents. Consider planning your road trip on a weekday to avoid the weekend congestion. Or, take an organized tour, which will help even more. Organized Hana day tours like this one help to alleviate traffic congestion on the Hana Highway, and take the driving responsibility off your hands! 
  • If you do drive, there are technically three strategies you can take: 
    • Driving to Hana from the north shore with stops, and then heading straight home the same way you came 
    • Driving all the way to Hana in the morning first, and then slowly exploring as you make your way back 
    • Taking the backside road from South Maui, which may save you a bit of time but is inadvisable due to sketchy roads. Most rental companies on Maui will not allow you to take your car here! We accidentally took this road not knowing, and in its current state, I just cannot recommend this road to visitors.
  • When driving, don’t illegally park, don’t enter private property, and make sure to carry out what you carry in. If you see what appear to be Maui residents in the car behind you, let them pass. This stretch of Maui is home to many locals, and they put up with large crowds and traffic on a daily basis.

Where to Stop on the Road to Hana:

  • Hookipa Beach
  • Twin Falls 
  • Waikamoi Ridge Trail 
  • Garden of Eden Arboretum 
  • Keanae Valley Overlook
  • Aunty Sandy’s Banana Bread
  • Halfway to Hana Food Stand (banana bread!)
  • Waikani Falls
  • Secret Lava Tube Cave
  • Makapipi Falls
  • Kahanu Gardens
  • Nahiku Landing 
  • Nahiku Marketplace
  • Wai’anapanapa Black Sand Beach (reservations need to be made here first
  • Hana town
  • Wailua Falls
  • Hamoa Beach
  • Koki Beach
  • ‘O’heo Gulch – 7 Sacred Pools
  • Pipiwai Trail 
  • Alelele Falls

Haleakala National Park – Kipahulu District

Rachel Off Duty: Haleakala National Park Pipiwai Trail
Rachel Off Duty: Haleakala National Park Pipiwai Trail

Two days ago you were at the summit of Haleakala National Park. Now, you’ll get to see the sea-level Kipahulu District! 

At the base of Haleakala, the Kipahulu District is a lush, densely forested oasis, with waterfalls and swimming holes you can hike to and enjoy. 

Swim in the Seven Sacred Pools (‘Ohe’o) and take the 4-mile out-and-back Pipiwai Trail, where you’ll find Waimoku Falls and an exquisite bamboo forest. 

Pro Tip: The entrance to Haleakala National Park is $30. You should have received a national park 7-day entrance pass when you entered the national park for sunrise / sunset two days ago. If not, you’ll need to pay the entrance admission here.

Alternatively, you can use your America the Beautiful Pass, which, for just $80, gets you free admission to all US national parks for a year! Get your America the Beautiful National Parks Pass here.

Pa’ia Town

You could easily spend a whole day in Pa’ia. But, to fit it into your 5 day Maui itinerary, plan to stop at Pa’ia either before your road trip (for breakfast) or after (for dinner and drinks). This laidback, hippie town has lots of great boutiques, galleries, and eateries to explore! 

  • Early Eats: Cafe Mambo, Pa’ia Bay Coffee Bar
  • Midday / Evening Eats: Pa’ia Fish Market, Tobi’s Shave Ice & Poke, nyloS Pa’ia, Mama’s Fish House (advance reservations strongly recommended for this one)

DAY FIVE: Wailea, Kihei, and South Shore Maui Beaches

Rachel Off Duty: 5 Day Maui Itinerary – South Shore Beaches

Whether or not you spend the night before near Hana, you’re probably going to want to spend your last day in Maui relaxing beachside. Day 5 of your 5 day Maui itinerary is all about kicking back, taking it easy, and drinking in all of the incredible Maui adventures you experienced over the past five days. 

Kihei and Wailea Towns

Depending on where you’re staying on Maui, you might not have visited the south Maui towns of Wailea and Kihei yet. These two communities are more developed for tourists, with Wailea being the more upscale of the two (think golf courses, the Maui Four Seasons, high-end shopping, and fine dining). 

The Shops at Wailea is where you’ll find the best selection of designer names and high-end boutiques on the island. 

South Maui Beaches

After a morning of shopping or grabbing breakfast, head to one of south Maui’s beautiful beaches to spend the rest of your day. Lucky for you, there are plenty of beaches in this area to choose from! My personal favorite is Makena Beach, also known as Big Beach. But, there’s more to choose from than just this.

Some South Maui Beaches to Visit:

  • Makena Beach (Big Beach) is picturesque and perfect for laying out, but the shorebreak is known for being pretty intense 
  • Little Beach is unofficially a ‘clothes-optional’ beach tucked away next to Big Beach 
  • Wailea Beach
  • Po’olenalena Beach 
  • One’uli Beach 

Maui Brewing Company

Rachel Off Duty: 5 Day Maui Itinerary – Maui Brewing Company

When you’ve had your fill of surf, sea, and sun, finish your day with a stop at Maui Brewing Company in Kihei. What started as a single brewpub in 2005 now has made a name for itself on a national scale. You might’ve even seen Maui Brewing cans at grocery stores where you live!

Go visit the brewery and enjoy a pint (or a flight), plus food, at their onsite beer garden, which boasts 36 craft and specialty beers on tap.

They don’t take reservations unfortunately, but the brewery is pretty spacious and accommodating. For the best experience, try to make it to their daily happy hour (3:30 – 5:30 pm) or their nightly live music (6:30 – 8:30).

Other Things to Do if You Have More Time

Rachel Off Duty: How to Spend 5 Days in Maui – Go Surfing

While these next suggestions might not fit in a 5 day Maui itinerary, consider looking into some of these if you have more than 5 days to spare!

  • Take a Day Trip to Lana’i: When it comes to choosing which Hawaiian island to visit, Lana’i is definitely one of the more expensive islands in the state. The island is famous for its sparse but very luxe accommodations (with rooms starting at $400+ per night) and secluded beaches. But, that doesn’t mean Lana’i is an impossible visit! In fact, you can actually take a day trip to Lana’i from Maui! Go on your own by booking a spot on the Go Lanai Ferry ($30 each way) or take a preorganized day trip like this one or this one.
  • Snorkel at Molokini Crater: If you didn’t get a chance to snorkel at Molokini crater during your first 5 days in Maui, now is your chance! Book a half- or full-day adventure to snorkel in this marine and seabird sanctuary. These tours typically come with food (and occasionally, drinks) and snorkel gear included as well.
  • Try a Surfing Class: Maybe your first 5 days in Maui were spent hiking and beach bumming. Nothing wrong with that! But as Maui is where I learned to catch my first waves, I’m biased – learning to surf on this island is a must for any first-timer. Take a lesson with woman-owned Maui Surfer Girls, and you might surprise yourself!
  • Go to a Luau: In Hawaiian culture, luau are big gatherings to commemorate special occasions and to welcome visitors. Though pricey, attending a luau is regarded as a ‘must’ for first-time Hawaii visitors, and generally comes with an evening of entertainment, tons of local Hawaiian food, and drinks. Check out Old Lahaina Luau and Feast at Lele, and be sure to book in advance.
  • Take a Helicopter Tour: One of the best perspectives of any Hawaiian island is from up high. While helicopter tours in Maui are pretty expensive, they’re well worth the experience if you can swing it. In Maui, you’ll want to check out AirMaui or see all Maui helicopter tours here.
  • Volunteer and Give Back to Maui: Spending the morning volunteering on Maui is a great way to give back to your favorite vacation destination. Some suggestions to malama (‘care for’) Maui include spending a morning learning about the culture and practices of Hawaiian land stewardship at Kipuka Olowalu, or cleaning the beach with the Hawai’i Wildlife Fund.

RELATED: 20+ Of the Very Best Things to Do on Maui

Where to Stay on Maui

Rachel Off Duty: Where to Stay on Maui
  • Camp Olowalu (Lahaina / Olowalu): Pictured above, this is the only place to go glamping on Maui! Or, if you’re into traditional camping, set up your tent just steps from the beach and enjoy Camp Olowalu’s amenities, like fire pits, bathrooms, showers, and grills.
  • Ho’oilo House (Lahaina): A luxe bed & breakfast in west Maui with Bali-meets-Hawaii style decor and amenities. I’m hoping to stay here myself the next time I’m in Maui!
  • Four Seasons (Wailea): If you’re looking for a resort experience, the Four Seasons in Wailea, nestled in Maui’s most high-end district, will do the trick.
  • Fairmont Kea Lani (Wailea): The ultra-high-end resort property in Wailea, Fairmont Kea Lani, is another place I have been curious to stay. If you stay here, let me know how it is in the comments!
  • Pa’ia Inn (Pa’ia): Yet another place on my wish list, the chic, small Pa’ia Inn is located right in the heart of Pa’ia town. It’s a perfect gateway to the road to Hana, or the perfect home base for a laidback stay on Maui’s north shore.
  • Hana-Maui Resort (Hana): Word on the street is that this is one of the most high-end accommodations in Hana, and you will be pampered here. Worth the road trip? You tell me!
  • Other Hotel Options in Maui (Click Here)
  • Maui Airbnbs (Click Here)

PRO TIP: Some Maui hotels will give you a discount or a free night’s stay just for volunteering! It’s part of Hawaii’s Malama Hawaii initiative, which you can get involved with during your trip.

See all volunteering options and participating hotels here.

Where to Eat and Drink on Maui

Rachel Off Duty: Where to Eat and Drink on Maui
Rachel Off Duty: Where to Eat and Drink on Maui

This 5 day Maui itinerary wouldn’t be complete without talking about where to eat and drink on Maui. Here are a few places I’ve tried during my most recent visit and recommend!

Other Tips to Know Before You Go

Rachel Off Duty: Maui Travel Tips
  • Currency: The Hawaiian islands use the US Dollar (USD). Credit cards are widely accepted, but carry spare cash for food trucks, tipping at hotels, etc.
  • Language: Hawaii is the only state with two official languages: English and Hawaiian. However, English is the language you’ll use to chat, get around, and read on street signs. You’ll also hear a third ‘language,’ called Pidgin, which is a sort of English creole formed over the past two centuries as various generations of immigrants began coexisting here. Today, it all blends together into a unique version of colloquial English you won’t hear anywhere else 🙂
  • Transportation: If you’re staying in Lahaina, Wailea, or Kihei and only plan on spending all your time at the beach during your 5 day Maui itinerary, you might be able to get by without a car. However, renting a car is going to be the best way to see Maui and successfully do this itinerary.
    • Renting a Car on Maui: Use Kayak to compare rental car rates or Turo to find peer-to-peer car rentals. At the time of writing this post, Hui, a locally owned peer car rental company, is only available in Oahu, unfortunately.
    • Renting a Camper or RV: Use RVshare to look up Hawaii RVs, camper vans, and the occasional rooftop tent. This option is perfect if you plan on spending a night camping in up in Haleakala or beachside near Hana.
    • Rideshare on Maui: Uber and Lyft are both easily accessible on Maui. Another contender is locally-owned Holoholo, which functions the same way as the other rideshare apps you’re already used to.
    • Public Transportation on Maui: The public bus system, called Maui Bus, is a generally reliable and inexpensive way to explore the island. Maui Bus services Central, South, West, Haiku, Kula and Upcountry Maui.
    • Kaanapali Trolley: If you’re staying in the Kaanapali resort area, this trolley can help you get around the resort area without a car or a long walk.
  • When is the Best Time to Visit Maui? Because of Maui’s ideal climate, there is no “bad” time to visit Maui. In general, peak season for Maui travel is in the summer and around the holidays. So, if you want to avoid the crowds during your 5 day Maui itinerary, go in the spring or fall. On the flip side, if you’re specifically looking for whale watching in Maui, you’ll want to plan your trip between late November and April.
  • Etiquette for First-Time Visitors: To avoid any unfortunate travel bloops, be sure to check out my Hawaii trip planning guide next. This breaks down everything you’ll want to know before you go to Hawaii! Safe travels!

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5 Days of Adventures on Maui
5 Days of Adventures on Maui

Hey there! I’m Rachel, a travel writer and a full-time advertising / marketing expert. In 2019, I traveled more than 25 times while working 9 to 5, and since then I’ve committed myself to living a more adventurous life, even if it means bringing my laptop along for the ride.

Are you hungry to travel more, but overwhelmed with how to juggle work and play? You’ve come to the right place!

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