Maui Itinerary: How to Plan the Perfect 5 Days on Maui Hawaii

Maui Itinerary: How to Plan the Perfect 5 Days on Maui Hawaii

This Maui beach with palm trees and turquoise water is part of this 5 days in Maui itinerary.

Ah, Maui. Does anything beat the golden sunrises from this Hawaiian island’s volcanic peak, or window-down drives along the rain forests and wave-lashed coastal cliffs? This Maui itinerary wraps these bucket-list busting experiences into 5 days of beach hoping 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 lovers of the Valley Isle, we find ourselves returning to many of these same activities time and again.

There’s no need to be rigid with this schedule, rather mix up the days as you see fit depending on where you’re staying on Maui and what you like to do. We’ve broken it down into different zones of the island you’ll likely want to see, so these can easily be rearranged. Here for a longer visit? You can’t go wrong sneaking extra time on the sand between these organized days.

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Maui Itinerary for 5 Days

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.

Front Street in Lahaina, Maui, with storefronts on one side and ocean with boasts on the other side. Boat rides are one of many things to do in Lahaina.

For a taste of island history, start with a visit to Lahaina Town, a one-time whaling village and former capital of the Kingdom of Hawaii. Old-timey Front Street here bustles with open-air cafes, galleries and so many shops sandwiched together in painted, timber storefronts with shady awnings. If you’re looking for things to do in Lahaina beyond shopping and pigging out on fried fish, head towards Lahaina Banyan Court to hang out under the weaving limbs of the massive 1800s tree and pop into the Old Lahaina Courthouse for art exhibitions. The neighboring harbor is a popular launching spot for boating excursions.

Next up, the Kaanapali Beachwalk, a fab way to spy out the fancy oceanfront resorts in this neighborhood. 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.

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.

Sunsets on the west side of the island are simply spectacular, and if you’re vacationing with a significant other, a twilight sailing will definitely score some romance points and be the perfect end to the day. Sunset cruises depart from Lahaina and can include anything from simple appetizers and drinks to a chef-prepared, gourmet dinner.

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.

Boat rides for snorkeling Maui and Lanai ferry on the water in front of island.

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.

Some Maui snorkeling tours even include perks like barbecue lunches and underwater scooters.

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.

Most Molokini snorkeling tours last several hours and include breakfast and/or lunch and stops at a couple of sites. If you’re curious about scuba diving but not yet certified, some excursions offer the chance to try snuba, a hybrid that allows you to go deeper under the surface than snorkeling without having to carry your own tank.

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).

GetYourGuide has whale watching excursions and dolphin tours from the Lahaina and Maalaea harbors. They typically range from two hours to half a day, with the longer options including buffet lunches and snorkeling as well.

Lanai day trips

It may be the smallest of Hawaii’s inhabited islands, but that doesn’t mean Lanai should be skipped, especially since it’s 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 floats back and forth from Lahaina 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.

Lanai tours typically wrap in underwater sightseeing and wildlife spotting since bottlenose dolphins, monk seals and sea turtles like to hang around these parts.

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 with surfers riding small waves crashing on golden sand.

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, with vendors on hand to dole out SUP boards and other water toys. It’s easy to waste away 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.

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.

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.

Nearby, but hidden among the stately houses and stone walls, Makena Cove is missable but for the increase in cars parked along the street and a little sign noting “shoreline access.” Heralded as a “secret beach,” the compact patch of sand is a favorite for snapping wedding photos or saying vows surrounded by palms and for catching sunsets over Kahoolawe (crescent-shaped Molokini is also in eyeshot). 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.

A jeep on the Road to Hana stops by the side of the road next to a black beach on the ocean.

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).

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.

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 choose to spend the night here to really stretch out the journey (switch day five’s sunrise to sunset to make this work), but we find it’s doable in a day if you get started early enough. We 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 and the Hana Cultural Center are other common tourist haunts.

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 Kipahula District of Haleakala National Park, but you’ll have to pay the entry fee to access the park and pools.

From here, 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 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.

If you'd rather kick back and enjoy the sceneray along the Road to Hana on an escorted day trip, check out this sightseeing tour from GetYourGuide. It includes perks like hotel pickup and meals.

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 some trails in the volcanic surrounds, 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 hours away.

The Haleakala National Park sunrise from the top of the volcano.

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.

If you’re not a morning person or can’t stomach the idea of driving weaving mountain roads 10,000 feet high in the pitch black, you can reserve a Haleakala sunrise tour to pick you up from your hotel and escort you to the park’s visitor center in plenty of time for the colorful show. As a bonus, many of these excursions will have warm gear you can borrow so you don’t have to pack your own (temps at the summit are often below freezing) and include a hearty breakfast afterward.

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.

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.

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.

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