Planning / What to Do

The Best 5 Day Maui Itinerary for First Timers + FREE Spreadsheet Planner

Looking for a foolproof five-day Maui itinerary for your first trip to the island? While it’s impossible to see everything on the island in five days — or even five weeks! — you can still experience many of Maui’s best sights in five days. 

As frequent visitors to the island, this is the five day itinerary we recommend for first timers — or for those who haven’t been back to the island in years. 

Scroll down to the end of this post for a special treat — the Google Sheets spreadsheet I use to plan ALL of my trips, including every Maui vacation.  

wide angle view of ocean from Lahaina Pali Trail
The view from Lahaina Pali Trail.

In this post:

Tips for planning the perfect 5-day Maui itinerary

Your perfect Maui vacation doesn’t have to mirror everyone else’s. But the most popular activities and sights on the island draw crowds for a reason. So we collected all the top activities for Maui vacationers. Then we narrowed the list to our recommendations for the very best things to do within a 5-day timeline.

View of ocean and beach with twigs in the foreground
View from the bluff at Makena State Park beach.

To maximize time, we also grouped activities together by location. That means less time wasted driving back and forth around the island.

Just remember: you do you. If our itinerary seems like too much, take things as fast or slow as you prefer. Swap out one activity for another must-do that speaks to you. Prioritize and identify your “must do’s” versus the “nice to do if there’s time.” 

Above all, don’t forget to stop and enjoy the moment when you’re on Maui. 

Tips for booking flights

The post-pandemic travel surge and airline staffing challenges have thrown a wrench into the typical high and low seasons on Maui. Seasons when Maui typically experiences a drop in visitors may see higher-than-normal counts, and vice versa. 

view of airplane wing in flight with clouds
Photo credit: Ross Parmly on Unsplash

Regardless, our tips for finding deals on flights remain the same:

  • Use a flight search engine such as Google Flights to comparison shop multiple airlines at the same time. 
  • Analyze Google Flights price graphs and trackers to get an idea of price fluctuations based on different dates.
  • If you’re able, you’ll get the best deals when you’re flexible on dates. For example, I once planned a trip to Maui on the first of November. Looking up flight prices, I realized that leaving a day early, on October 31, would cost 50% less than flying the next day. I booked the less expensive flight.    
  • Use a mobile app such as Hopper, which analyzes flight data and predicts future prices. Based on the data, the app recommends whether to book now or wait until prices fall.

How to decide where to stay

Accommodation costs tend to make up most of the Maui vacation budget. But with so many options, where should you stay? These are the different districts on Maui, and the types of lodging you can expect to find there.

The grounds at Kamaole Sands Resort in South Maui.
  • West or South Maui. Most visitors stay in either West Maui (Lahaina, Kaanapali, or Kapalua) or South Maui (Kihei, Wailea, or Makena), simply because that’s where most of the resorts and hotels are located. Trying to narrow down between West Maui and South Maui? We explore the two regions in Is West Maui or South Maui Better? Here’s the Lowdown.
  • North Maui. Other options include Maui’s north shore, around Paia and Haiku, where you can find short term vacation rentals, boutique hotels, and hostels. You won’t find resorts on this part of the island.
  • East Maui. Staying on the east side of the island, near Hana, you’ll find unique accommodations such as short-term rental cottages. In Hana itself, you can also stay at the boutique resort Hana Maui, a Hyatt property. Staying in or around Hana, you’ll enjoy an immersive experience that you won’t find on a single day trip. However, it’s more difficult to access the rest of the island when you’re staying along Maui’s eastern shore. 
  • Upcountry. Staying in an upcountry town (such as Kula, Pukulani, and Makawao) gives visitors a more rural and farm-centric feel. It’s a closer drive from upcountry to other parts of the island when compared to Hana. But it can also be a significant drive from this part of the island if you’re planning a beach day.

Can’t decide? Don’t pick just one. Instead, split up your stay. Spend a few days in West Maui or South Maui, then overnight near Hana. Or enjoy the less crowded delights of Maui’s upcountry for a few nights before moving to the resort district for easy access to the beach.  

What to pack

Relaxed island wear is key when vacationing on Maui. Just don’t forget these essentials when you pull out the luggage bags before your trip:

  • Lightweight and casual clothing. Even with the breeze, it can get hot and humid on the island. Comfort is key here. Ditch the stilettos and suits in favor of sandals and sarongs. Think laid back resort style, not runway chic. 
  • Swimwear. Bring a few sets of swimsuits so that one can dry out while you wear the other.
  • Sun protection. And not just reef-safe sunscreen. Hats and sunglasses are a must, too.
  • Hiking shoes. While you can make some hikes in sandals, other trails on Maui may have loose rocks, tree roots, mud, and water crossings. If you plan to hike these intermediate and advanced trails, you’ll be thankful for the support of a sturdy hiking shoe. 
  • At least one sweater. While the tropical sun keeps you toasty while touring the island, Maui’s tradewinds can bring chilling temps with it. Don’t get caught without a sweater — particularly at Haleakala National Park, on a sunset boat tour, or when dining near the water.

How to get around Maui

Do you need a car to get around Maui? We recommend renting one. A rental car is your best bet for flexibility getting around the island. No need to wait for a rideshare or worry about the lack of cell reception. The downside to driving? Parking can be a bear in certain areas.

Row of cars in a gravel parking lot
Parking at Twin Falls on Hana Highway.

Rideshare apps such as Uber or Lyft work well in heavily trafficked or tourist areas — we’ve had good luck hailing a driver from Kahului airport, for example. You shouldn’t have a problem in areas such as Lahaina or Wailea. But you probably won’t find a driver at farther off spots such as the Road to Hana or less populated parts of upcountry. 

Public transportation isn’t your best bet, because it won’t take you to all the parts of the island in a timely manner. If you plan to visit several sites in one day, the bus schedule probably won’t match the timing you need.

Maui itinerary day 0: Fly to Maui and settle in

You’ve just spent hours on a long flight to the island. It may be tempting to jump right in and start touring the island. Don’t do it! 

Instead, give your body a chance to recover from airport lines, stuffy plane seats, and the time change. Settle into your hotel, grab some essentials, and get your bearings before tackling your Maui bucket list. 

Pick up essentials

An aisle filled with products inside of the Kahului Costco.
Costco members can pick up essentials from the Kahului location.

There are several shops near the Kahului OGG Airport where you can pick up the basic travel essentials you may need for your trip. Reef-safe sunscreen? Check. Maui Gold pineapple? Check. Toothbrush you forgot to pack? Check.

Kahului has plenty of options. We like Target or Walmart’s curbside pickup service. If you’re traveling with a large group, Costco is another option. 

Check into your hotel

From the Kahului area, head to your hotel. You’ll spend around 45 minutes to an hour in the car if you’re staying in West Maui, or around half an hour if you’re booked in South Maui. 

Grab some grub

Plated salad topped with soft boiled eggs and vegetables

All the travel excitement has probably worked up your appetite. Ask the hotel staff for recommendations on their favorite nearby food stops. And don’t forget to check our list of 13 Local Dishes You Need to Try When You’re in Maui

Relax and enjoy sunset on the beach

Sunset view from the beach at Kamaole Sands III in Kihei.
Sunset at Kamaole Sands III

If you haven’t completely conked out in exhaustion at this point, stroll to the beach for your first Maui sunset. 

Then get plenty of rest! You have lots ahead of you.

Maui itinerary day 1: Haleakala sunrise and Upcountry

Instead of heading straight to the beach on your first full day, we recommend seeing some of the most unique regions of the island — the volcano that makes up 75% of Maui’s landmass and the rural roads of the Upcountry district. 

Sunrise viewing at Haleakala National Park

Remember when I said you should rest up on your first night on Maui? That’s because we recommend waking up pre-dawn for a sunrise viewing at a dormant volcano — Haleakala.  

Photo credit: Hawaii Tourism Authority (HTA) / Tor Johnson

Why get up so early on your vacation to see some old lava rocks? Sunrise at Haleakala is one of the most coveted reservations on the island — even more exclusive than dinner at Mama’s Fish House. If you’re lucky enough to snag a spot on the summit for your chosen morning, you’re in for one of the most breathtaking sights you’ll encounter on Maui. 

If you fly to Maui from the continental U.S., chances are you’ll be up early because of the time change, anyhow. 

For safety, leave early from your hotel and take your time driving up the volcano road’s switchbacks.  

While you’re near the summit, explore some of Haleakala’s trails (such as Hosmer Grove) before heading down the mountain for breakfast.

Breakfast at Kula Lodge Restaurant

After an early start and surviving the winding road up Haleakala, pull over at the Kula Lodge Restaurant on your drive down. The rustic spot boasts scenic views of the valley below from both the dining room and outdoor terrace. Wander through the garden terrace and marvel at the impressive landscaping.  

For breakfast, try the classic eggs benedict or malted Belgian waffle with strawberries. If you arrive around lunchtime, ask about the pineapple upside down cake. Delish!

The Kula Market Place next door is also a worthwhile stop for local souvenirs and treats. 

Explore the cowboy town of Makawao

Makawao is best known as Maui’s cowboy, or paniolo, town. In the late 1800s, ranching expanded in this upcountry area, bringing paniolo with it. 

Storefronts on Makawao’s main strip retain the architectural style of the early 20th century — a blend of Hawaiian plantation and old western town motifs.  

Today, visitors meander the Baldwin Avenue shops and art galleries in Maui’s historic cowboy town. 

Stop at T. Komoda Store and Bakery. The 100-plus year-old establishment serves some of Maui’s most famous malasadas. Grab a few of the sugary treats, conveniently served on a stick.

Then duck into Maui Cookie Lady’s cozy shop. A favorite with celebrities such as Dwayne Johnson and Ludacris, the hefty cookies are individually wrapped so that you can pick up a few to enjoy later. 

Cuddle goats at Haleakala Creamery

A woman faces goats standing against a fence line
Feeding treats to the goat herd at Haleakala Creamery.

Get an up close look at some adorable goat faces at Haleakala Creamery. Book an advance tour to gain access to tasting and a tour at this unique upcountry dairy farm. You may spy their small batch caramel sauce at retailer shops around the island. 

Not only will the owners treat you to a tasting, but you’ll get a chance to tour the commercial kitchen and feed treats to the goat herd. 

Maui itinerary day 2: West Maui hike and ocean sail

Many island visitors stay at the West Maui resort districts of Kaanapali and Kapalua. And for good reason. This part of Maui enjoys an abundance of must-try restaurants, shopping opportunities, and sightseeing opportunities for all ages. 

Hike Waihee Ridge or Iao Valley

Scenic mountain view overlooking greenery and clouds
View from the Waihee Ridge Trail.

Stretch your legs and scale a West Maui mountain for epic above-the-clouds views at Waihee Ridge Trail. Not for the faint of heart (or knees), Waihee Ridge challenges hikers to a 1,500-foot ascent on this 2.5-mile hike.  

For a less strenuous venture, visit the Iao Valley State Monument. The paved 0.6-mile walk leads you to a scenic viewpoint of the Iao Needle, a 1,200-foot geological landmark that shoots up from the valley floor. 

After your hike, stop at Leoda’s Kitchen and Pie Shop for their famous Olowalu lime or chocolate haupia pie. 

Note: Iao Valley will be closed for improvement projects between August 1, 2022 and January 15, 2023.

Meander historic Lahaina town

Explore waterfront Front Street in historic (and typically crowded) Lahaina. Keep your eyes peeled for parking spots, which are hard to come by. 

Even with the crowds, spending a few hours on Front Street won’t be wasted. Boutique shops, restaurants, and art galleries line the main thoroughfare.  

Cool down from the heat with shave ice at Ulululani’s. Then snap a selfie in front of the oldest banyan tree on the island. Or learn some area history at the Baldwin Home Museum.

Sail away (and back)

Slip on a pair of sunglasses and head to Lahaina Harbor for a luxurious cruise off of Maui’s shoreline. Choose between a cocktail cruise, whale watching, snorkel tour, or sunset dinner aboard your tour provider’s catamaran or sailboat. 

Maui itinerary day 3: Road to Hana

If you like road trips, the winding Road to Hana remains one of Maui’s most popular adventures. If you venture past Hana, the trip out and back will take you most of the day. These are our favorite things to do along Hana Highway. For more, check out our list of 18 Best Road to Hana Stops

Head to a waterfall (or two)

Waterfall at the Oheo Gulch on Maui Hawaii.
Waterfall at Oheo Gulch along the Road to Hana.

You can park in a designated lot and hike to a waterfall (such as at Twin Falls Maui), or slow down at one of the many hairpin turns to view waterfalls along the road. 

Nosh on Maui’s most famous banana bread

Outdoor sign for Aunty Sandy's Famous Banana Bread along the Road to Hana on Maui.

Off of a small offshoot road along the Keanae Peninsula, head to Aunty Sandy’s Banana Bread stand. They have the best banana bread on the island (in my humble opinion). If you don’t trust me, Gordon Ramsey visited the popular banana bread purveyor and gave the sweet loaf a rave review.

Sink your toes into a black sand beach

View of ocean from a black sand beach
The black sand beach at Waianapanapa State Park along Hana Highway.

You need to plan ahead before visiting the famous black sand beach at Waianapanapa State Park — advance reservations for set time slots are required. 

Once you gain entry, admire the remnants of a once-active volcano. Formed from the reaction when molten lava once flowed to the ocean water, a visit to the black sand beach is another Hawaii must do. 

Hike through an ethereal bamboo forest

A woman walks up the stone stairway at the Pipiwai Trail bamboo forest on Maui, Hawaii.
Walking through the bamboo forest at Pipiwai Trail.

Drive past Hana for one of the most impressive hikes along the Road to Hana. The out-and-back Pipiwai Trail hike leads you past a sprawling banyan tree, waterfalls, and towering bamboo canes. 

When you get back to the trailhead, take the short half-mile walk toward the ocean to Oheo Gulch (a.k.a. Seven Sacred Pools). While swimming is prohibited as of 2022, the overlook and stunning vista is worth the short trek. 

Pro tip: If you visited Haleakala for sunrise (or sunset) earlier in the week, save your receipt. This hike is located within the bounds of Haleakala National Park. If you visit both the summit and the Pipiwai Trail hike within three days, you only have to pay once. Simply present your receipt on the second visit, and you aren’t subject to the entry fee a second time.

Maui itinerary day 4: South Maui beach break

After a long day on the Road to Hana, it’s time to let the South Maui ocean waters soothe the soul. Start off with a tour at one of Hawaii’s most revered snorkeling spots. Then set out to see a bit of South Maui on foot. After you work up an appetite, grab a bite at one of our favorite Wailea restaurants. Finally, settle onto the sand at Maui’s biggest beach. Let the sound of the waves lull you into relaxation mode as you soak in the island sun.

Snorkel at Molokini Crater

Considered to have the clearest water for snorkeling in Hawaii, Molokini Crater is a must-do if you want to snorkel in Maui waters. You won’t be able to access this spot directly from a Maui beach, though. You can only get there by boat. We’ve sailed with and recommend Kai Kanani’s Signature Deluxe Snorkel tour. The Kai Kanani tour sails to Molokini early in the morning — before other tour boats show up. So you’ll have a head start snorkeling away from the crowds. 

Not only does the tour provide a snorkel excursion at Molokini, you’ll also have a chance to snorkel with Hawaiian green sea turtles at Turtle Town, where the turtles congregate. 

Hike a lava field or stroll down the Wailea resort beach path

Two men walking in the distance on a rocky trail
Lava field hike at Hoapili Trail in South Maui.

After you’ve dried off from your snorkeling adventure, lace up your hiking shoes for a lava field hike at Hoapili Trail. The 5.5-mile round trip journey gets hot, so don’t forget to pack water, a hat, and sunglasses before you start your trek.

If you’re looking for a leisurely walk instead of a hike, get an up-close view of Wailea’s swanky resort district — and the amazing ocean views — at the Wailea Resort Beach Path

The beach path starts, at the southern end, from Polo Beach Park. Walking north, follow the easy paved trail north along shore. The north end of the beach path terminates at the Andaz Resort. 

Refuel at Monkeypod Kitchen

Three tacos at Monkeypod Kitchen in Wailea Maui.
Bulgogi tacos at Monkeypod Kitchen.

After an active morning in the water and walking the coast, pop over to Monkeypod Kitchen. You’re probably famished at this point. 

Monkeypod is known for having the best Mai Tais on Maui, but their pies are pretty tasty, too. Share a chicken wing appetizer and the kalua pork pizza. My favorite dish? Their bulgogi pork tacos.  

Take a beach break at Makena State Park (or a nearby beach)

Couple getting married on a rocky bluff
View from the bluff at Makena State Park beach.

After an active morning of snorkeling and trekking on foot, you deserve some relaxation time. Grab a spot on the sand at Makena State Park, also known as Big Beach. The beach is one of the biggest on Maui, hence its name. Remain cautious of the waves here. It’s usually too rough for swimming.

If you can’t sit still and are up for exploring, Little Beach and picturesque Secret Beach are also nearby. 

But a word of caution: While nudity is prohibited, it’s common to find unclothed beachgoers at Little Beach. You’ve been warned. 

Maui itinerary day 5: North shore and Paia town before flying home

It may be your last day on Maui, but you can still squeeze in a few vacation memories before you jet off. We recommend visiting Hookipa Beach and Paia town on your last day because both are fairly close to the airport. And you don’t need an entire day to visit either spot.

Turtle watch at Hookipa Beach

Hawaiian green sea turtles on a beach and a sign restricting entry
Hawaiian green sea turtles at Hookipa Beach.

One your final day, find a perfect viewing spot to see some of Hawaii’s most famous and endeared residents — the green sea turtles (or Hawaiian honu). You’re nearly guaranteed a look at the mellow creatures at Hookipa Beach. 

Nicknamed Turtle Beach for its routine turtle visits, Hookipa lies just two miles east of Paia town. And you won’t have to walk far (or get in the water) to see the turtles. They normally settle on the sand not far from the lower parking lot for long sunbathing sessions.  

Tour Paia town

View of storefronts at Paia town.
Paia town storefronts.

Just a 15 minute drive from Kahului’s OGG Airport (without traffic), historic Paia town is small enough for a few hours’ visit before you hop on the plane home. What was once a sugar plantation town, Paia has since reinvented itself as a haven for surfers, artists, and bohemian hippies. Visitors come to Paia for its upbeat beach vibe, restaurants, art galleries, health food, and shops. 

We recommend grabbing a last bite of Maui fare at either Cafe Mambo or Paia Fish Market. For dessert, stroll by Artisan Ice Cream for a fresh cone and sweet scoop. 

Plan your trip using our FREE vacation planner spreadsheet

This is the same spreadsheet I use to plan all of my trips, whether I’m traveling to Maui or another destination. Personalize your vacation plans by moving activities around, swapping out hiking trails for more beach breaks, and more.

Click to download a free copy of our Maui trip planning spreadsheet with Google Sheets. To edit your own copy, click the upper right hand cell to highlight and select the entire sheet. Then click Edit > Copy to copy the sheet. Open a new Google Sheet under your own Google account and paste the contents into the new file.

You can also download a Microsoft Excel copy of the sheet by clicking File > Download.

About Author

Hi, I’m Gina — managing editor, Maui enthusiast, and human behind the keyboard here at Maui Trip Guide. When I’m not on the island at my Kihei condo, you can find me planning my next travel adventure from my home in the Pacific Northwest.

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