The Best 5 Day Maui Itinerary for Your First Time in Hawaii
This 5 days in Maui itinerary is full of golden beaches, mountain-top sunrises, gushing waterfalls and adventurous road trips.
Ah, Maui. Does anything beat the golden sunrises from this Hawaiian island’s volcanic peak, or window-down drives through rain forests and along wave-lashed coastal cliffs? This Maui itinerary wraps these bucket-list-busting experiences into five days of beach hopping and sightseeing from shore to shore on the island.
It’s an idyllic five days in Maui for first-timers since you’ll cover a lot of ground and most of the top-ranked “to-dos.” As a lover of the Valley Isle, I find myself returning to many of these same activities over and over.
There’s no need to be rigid with this schedule. You can mix up the days to fit where you’re staying and what you like to do. I’ve broken the agenda down into different zones of the island you’ll likely want to see.
Here for a longer visit? You can’t go wrong with spending extra time on the sand between these organized days.
Keep reading for how to spend 5 days on Maui Hawaii and scroll to the end for tips on where to stay and the best season to visit.
Editor’s Note: As the island recovers, it’s more important than ever to bolster the tourism industry by being a respectful visitor and supporting locally-owned businesses. Some of the activities in this post may be unavailable at this time. Please check the Hawaii Tourism Authority site for up-to-date information.
The Ultimate 5 Day Maui Itinerary
This 5 day Maui itinerary includes activities all around the island and excursions off the coast. The map below is color-coded by day on this itinerary so you can see how far different destinations are from each other.
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Grab our FREE Maui packing list before you leave for the island
Day 1 — West Maui
Things To Do in Lahaina and Kaanapali
A favorite with vacationers, West Maui holds treasures like the historic small town of Lahaina and the Kaanapali Beachwalk, with sands and surf to one side and buzzing restaurants and massive resort properties to the other.
If you’re staying in this region, it’ll likely be in one of the hotel and golfing hubs of Kaanapali or Kapalua, but be sure to get out and explore some of the local shops, farmers markets and food trucks that dot the area, too.
Lahaina Town
Lahaina Town is one of the most significant historic hubs on the island as the former capital of the Kingdom of Hawaii and a whaling village. More recently, the old-timey Front Street held open-air cafes, galleries, and shops in painted wooden storefronts with shady awnings. The Lahaina Banyon Court was a popular spot to hang out under the weaving limbs of a massive 1800s tree in front of the Old Lahaina Courthouse.
Unfortunately, almost all of this historic town was destroyed during a 2023 fire. It remains to be seen what will be recovered or rebuilt in the coming years.
It’s important to remember that this isn’t just a tourist destination but a home to many. When this area reopens to the public, please be respectful and visit responsibly, remembering that residents here recently experienced a great tragedy.
Kaanapali
The Kaanapali Beachwalk is a beautiful spot to stroll along the water and check out fancy oceanfront resorts. You can park for free at Hanakaoo Park — also a good spot for a beach day, thanks to its big swath of sand, restroom facilities, lifeguard station and picnic tables and grills.
The palm-shaded sidewalk path starts on the northern side of the park at the grounds of the Hyatt Regency Maui Resort and Spa and continues for a little more than a mile to the Sheraton Maui Resort and Spa. Along the way you’ll have sandy beaches to one side and lush gardens, resort pool decks and patio restaurants to the other.
You can even poke around the grounds of some of these luxe hotels (the Hyatt has penguins and swans onsite) or book a luau or dinner reservation.
Whalers Village
Along the beachfront path, Whalers Village is the spot to go for shopping and surf-and-turf. You’ll find that many of the retailers at this breezy mall fall into the islandy category — lots of surf gear, beach decor and activewear with a few jewelry shops between. Make sure to pay a visit to the Honolulu Cookie Company to score some samples.
Sunset Cruise
Day 2 — Excursions on the Water
Snorkeling Maui, Molokini and Lanai
Every day could be a beach day, but if you want to get out and explore a little, Maui excursions offer options to duck under the waves with colorful fishies, sail off in search of whales, and so much more. A lot of Maui adventures on the water depart from the Maalaea or Lahaina harbors, so you can tack on some local exploration after a half-day outing.
Maui Snorkeling Excursions
Snorkeling Maui is a great way to meet the diverse ecosystem that hides just under those cerulean waters we’re all so fond of. While plenty can be seen with a mask and fins just a quick swim offshore, a guided jaunt will help you uncover the best spots.
Often topping the list of prime destinations is Molokini, a volcanic crater off the south coast that pokes above the surface in a crescent shape. Designated a Marine Life Conservation District, the island and its surrounding coral host a couple hundred species of fish and other sea life like eels, manta rays, octopuses and dolphins.
Book Maui snorkeling tours on GetYourGuide
Wildlife Tours
Depending on the time of year you visit, Maui whale watching tours should be on the bucket list. Humpbacks migrate this way each winter and can be spotted breaching the surface from about December to April. Guided jaunts on catamarans help you view them from a safe distance, with some adding kayaking or snorkeling to the agenda, too.
If you’re vacationing outside whale season, dolphin cruises are another way to go. Spotted, spinner and bottlenose varieties leap around in these parts and some excursions even guarantee a sighting (and a do-over if they’re hiding).
Search for whale watching tours on GetYourGuide
Lanai Day Trips
Lanai is the smallest of Hawaii’s inhabited islands and conveniently close to Maui. Most folks come for a remote stay at the luxurious Four Seasons Resort, but you can also hop over for some sightseeing by taking the Lanai ferry. It goes back and forth from Maui a few times a day from early morning to evening, so you can sneak in a pretty full excursion or just stay for a few hours.
What is there to do on Lanai? Everything from pricey cliffside golf to rugged, dirt roads that require a ride via four-wheel drive or horseback to reach rock gardens, secluded beaches and views of a rusty shipwreck offshore.
If you want an organized Lanai day trip, those can be arranged, too. Lanai snorkeling excursions are the most popular path to the island, heading toward the surrounding reefs to spy out the vibrant sea life swimming around.
Check out these Lanai tours on GetYourGuide
Day 3 — South Maui
Things To Do in Wailea
Whether or not you’re staying in this part of the island, you’ll want to spend some time on the sands of South Maui. The Wailea area, in particular, is known for its ritzy resorts, pristine golf courses with a view, and tourist-centric shopping and dining. The best things to do in Wailea, though, don’t have to cost a penny — just make your way to the beach.
Wailea Beach
If you’re after a day on the sand, head straight for Wailea Beach, consistently noted as one of the world’s best. It’s easy to see why, with a wide patch of soft, golden shoreline surrounded by lush greenery and backed by a pair of plush resorts, and the islands of Lanai and Kahoolawe in the sight line.
There’s ample snorkeling, particularly by the rocky patches on either end, and regular rolling waves. Venders on the beach have SUP boards and other water toys. It’s easy to spend a whole day here, especially with the free parking, public facilities and nearby shopping and food, but it can get crowded for the same reasons.
Maluaka Beach
Heading south from Wailea, the road and coastline start to empty a bit, trading sleek hotels and name-brand dining for vacation rentals and taco food trucks. Maluaka Beach in these parts is a less-crowded alternative to Wailea Beach, though parking and restrooms are a little further of a walk from the sand.
Makena State Park
Keep following Makena Alanui Drive past all the golf courses and you’ll soon come upon Makena State Park, where undeveloped shores sit in the shadow of a dormant volcanic cone and amenities are a bit more rustic (i.e. portable toilets and no showers). Big Beach here is more than a mile long and has a lifeguard station while Little Beach is known for its clothing-optional vibe.
Makena Cove
Nearby, Makena Cove is hidden among the stately houses and stone walls. You’d almost miss it if it weren’t for all the cars parked along the street and a little sign noting “shoreline access.”
Known as a “secret beach,” the compact patch of sand is a favorite for snapping wedding photos or saying vows surrounded by palms. The sunsets over Kahoolawe and crescent-shaped Molokini are also incredible.
With thrashing shore break and lots of black and jagged volcanic rocks, it’s not the best for casual wading and swimming. But you’ll see lots of snorkelers testing the tide to peak underwater at the sea turtles that like to hang here.
Day 4 — Excursion to Hana
Road to Hana Tour and Stops
One of the most popular activities on every Maui itinerary, the Road to Hana is a winding drive full of waterfalls, lush greenery, rainbow eucalyptus trees, and scattered food stands full of fresh fruits and banana bread.
The destination is a remote town on the eastern tip of the island, but the experience is more about the journey. A few prime spots are mentioned below, but be sure to pick up a guide or download an app so you don’t miss anything.
Road to Hana Road Trip
Start your Road to Hana tour early in the morning to beat some of the crowds and allow yourself plenty of time to stop for hikes and swims. The path starts at Pa’ia, a colorful, beachy town full of restaurants and shops catering to the swarms of tourists that pass through and the last place to fill up the gas tank before Hana.
The Hana Highway along the east coast is pretty spectacular, rising from sandy beaches to rocky cliffs with violently crashing waves, winding around hairpin turns surrounded by damp green forest, and crossing one-way bridges over streams from gushing waterfalls.
Plotting out a few Road to Hana stops will help you to hit the highlights, but allow yourself time to go with the flow, pausing to pick up a fresh coconut or food truck snack (you’ll see lots of banana bread but smoke shacks with heartier eats are scattered along the road, too).
Road to Hana Stops
You’ll likely notice cars pulled over on the side of the road or the occasional parking lot at some of the top sights, including cascades like Twin Falls, Puohokomoa Falls and Waikani Falls. Natural attractions like these are free, but you’ll have to pay a fee to check out the famous Garden of Eden, an arboretum and botanical oasis full of walking trails, scenic lookouts and vibrant flowers.
While most stops are directly on the Hana Highway, a couple require pulling onto a side road, like Keanae Point with its crashing surf and historic church surrounded by palms, and Waianapanapa State Park, home to a black sand beach, jagged rock cliffs and vibrant green foliage. You need to make a reservation to visit Waianapanapa State Park.
Hana Town
The little town of Hana is only about 45 miles from your starting point in Paia, but you’ll likely need more than half a day to get there with a few stops along the way. Some folks spend the night here to really stretch out the journey (switch day five’s sunrise to sunset to make this work), but I find it’s doable in a day if you get started early enough.
I like to grab lunch from one of the food trucks in town and head over to Koki Beach Park, a quiet and rugged spot with strong surf. Hana Bay Beach Park is another public beach option closer to the town.
Haleakala National Park Kipahulu District
Past Hana, Wailua Falls is a popular swimming spot, as are the Seven Sacred Pools at Oheo (check if they’re open first). There are also trails in this area, the Kipahulu District of Haleakala National Park, but you’ll have to pay the entry fee to access the park and pools.
Road to Hana Backside & Piilani Highway
From Hana or Haleakala National Park, most road trippers turn around and head back the way they came, but continuing on along the southeast coast is a less-crowded option for a change in scenery.
You’ll have to brave a few bumpy miles on a one-way road that at times hugs some high cliffs with blind corners, but once you get past that dramatic drive, the path opens onto a well-paved run of the Piilani Highway with breathtaking volcanic scenery on the backside of Haleakala. Here, lava fields and canyons inland transition to wide open and elevated views of the ocean and coastline rock formations.
The road takes you to the upcountry district of Maui in the foothills of Haleakala, where we recommend spending the night to be closer to Haleakala National Park in the morning.
FYI: Many travel resources caution against driving the “backside” of the Road to Hana, citing the dangers of the blind corners, high cliffs and gravel roads. Some rental companies even include language in their contracts or warnings about taking this route (so don’t expect them to help if you get stuck or in an accident here).
If you go this way, use your best judgment, practice extreme caution on the one-way parts, drive slow, and honk when you’re going around corners to announce your presence. More and more travelers and small tour vans have started driving the route, so you likely won’t be the only car around.
Road to Hana Tours
Day 5 — Upcountry Maui
Haleakala Sunrise Tour and National Park
Your morning will start bright and early — correction, dark and early, since you’ll need to be up and moving hours before dawn breaks on the horizon to catch the glaring Haleakala sunrise from the national park’s summit.
Afterward, test out volcanic trails or head back down the mountain for a nap followed by beach time. We recommend this excursion for the first or last day of your trip with a stay in Upcountry the night before so you won’t have to wake up as early, since most other hotel hubs are a couple of hours away.
Haleakala Summit Sunrise
As the first spot to see the fiery sun dramatically break across the horizon on Maui, the Haleakala National Park sunrise tops many a bucket list. Depending on the time of year you visit, daybreak falls somewhere between 5:30 a.m. and 7 a.m., but you’ll need to wake up in the middle of the night to begin your trek.
The twisty drive up the mountain takes about an hour from the nearest hotels in Kula or closer to two hours from the resorts in Wailea or Kaanapali. Arrive at least an hour before sunrise to ensure you get a prime viewing spot and to spend some time watching stars shooting across the dark night skies.
Reservations are required, as is an entry fee to access the national park (save your receipt if you visited the Seven Pools side of Haleakala from Hana already to avoid paying twice). The summit building is the ultimate spot to watch from as it sees the first glimmer of light, but if that parking lot is full, you can try the Haleakala Visitor Center instead.
Haleakala National Park Summit District
While you’re up here, you might want to do some hiking and sightseeing in the summit district of Haleakala National Park. Pause at the Haleakala Visitor Center just below the summit to stare into the crater and check out a few exhibits. Trailheads dot the road back down the mountain and you’ll be able to see both sides of the island from scenic lookouts, too.
Upcountry Maui
The hills at the base of Haleakala are dotted with opulent estates (some belonging to celebs), and charming villages in an area known as Upcountry Maui. If you’re not in a rush to get back to the beach, today is the perfect day to explore this region.
Pop by Kula to visit a lavender farm and botanical garden or Makawao for a cowboy town turned arts hub with an old-timey downtown district full of galleries and boutiques.
Kahului
If you have a flight out in the evening, you can end your 5 days in Maui on the beaches near Kahului, like Kanaha Beach Park, a popular windsurfing and water sports hub.
Tips for Visiting Maui
This planning guide will help you make the most of your 5 days in Maui, with tips for when to go, what to pack, and where to stay.
Where to Stay on Maui
The two most popular hotel and condo zones are in West Maui and South Maui.
South Maui has budget-friendly condos and boutique hotels in Kihei and upscale, beachfront resorts in Wailea.
Other hotels and vacation rentals are scattered around the island in places like quiet Upcountry Maui for views, Hana for remote retreats, and Kahului for basic hostels and hotels near the airport.
This guide to where to stay on Maui includes the different types of accommodations to choose from, like resorts, condos, vacation rentals and more.
What to Pack for Maui
When packing for Maui, you’ll want to consider what types of activities you plan to do. Grab our Maui packing list and Hawaii packing list for everything you will need.
At the most basic, pack swimwear and beach gear, daytime outfits or resort wear, and casual evening attire like sundresses, linen pants, and light layers for cool breezes. If you plan to hike, add in some activewear and a rain jacket. With a 5 day Maui itinerary, you’ll want at least two swimsuits so one can be drying while you wear the other.
You can buy any necessities and toiletries you forget on the islands, but prices are often higher. Many hotels and resorts provide beach towels and some condos will have beach toys and snorkels, too, so check with your accommodations to see what all is included.
How to Get to Maui
Maui’s main flight hub is Kahului Airport on the north coast. Domestic, international and inter-island routes land here from about 10 different airlines, including several major carriers. Since Maui is centrally located in the Hawaiian Islands, direct flights from places like Oahu, Kauai and the Big Island take less than an hour.
How to Get Around on Maui
Most big hotels can arrange a shuttle service from the airport. Taxis, public buses, rideshares and tours are also available if you don’t plan to leave your resort area very often.
However, renting a car is by far the best (and often most economical) way to see the island on a Maui 5 day itinerary. Most resort towns are 30 minutes to an hour from the airport, and activities like the Road to Hana drive require either a private vehicle or a guided tour. Just be sure to reserve your rental car as far in advance as possible to make sure one is available!
How Many Days on Maui
You will never want to leave Maui, and there are enough beaches, hikes, road trips and adventures to easily fill a week or more on the island. At a minimum, though, I recommend three days on Maui if you are island hopping or five days on Maui if this is your only stop.
Any less than that will not allow enough time for bucket list activities like the Road to Hana. With a full week, you will be able to add in excursions like snorkeling at Molokini or a day trip to Lanai. Here’s out guide to spending four days on Maui.
Visiting Oahu, too? Here’s how to spend 4 days on Oahu.
Seasons and Weather
Maui’s balmy days and cool evenings are a year-round treat, but there are a few differences between the winter and summer seasons.
Winter, generally November through April, has average highs in the upper 70s and lows in the upper 60s. This is the rainier season, but much of the wet weather occurs in the upper elevations and on the windward side of the island, which is not where most resorts are located. Waves and currents are also larger and stronger in winter on the north shore.
May to October is the summer season, with highs in the mid-80s and nighttime lows in the 70s. Beaches are usually calmer in summer, but strong currents can be a hazard at any time. Since summers are drier, some waterfalls dry up as well.
Maui has a much colder microclimate in the Upcountry and especially as you head toward the peak of Haleakala. Temperatures at the summit drop below freezing and it can even snow occasionally. If you visit Haleakala National Park for the summit sunrise, you’ll want to dress very warmly and bring blankets!
