5 Day Maui Itinerary: The Best Things To Do

By | Digital Editor
Last Updated: May 1, 2023
Watching the sunset on one of Maui's many beautiful beaches is a must do activity

Maui, an enchanting Hawaiian island deep in the Pacific, is a paradise for all traveling styles. It is the second largest of the eight main islands that comprise Hawaii. Whether you’re looking to stay active with hiking, diving, or snorkeling, play golf, fish, dine, or bask in the sun by the pool or beach, Maui’s divergent landscapes have you covered. From Haleakala National Park, soaring cliffs, soft-sanded beaches, dried lava, bamboo forests, to waterfalls and the Pacific Ocean, Maui is a year-round dream destination.

Maui Travel Guide - The Best Things To Do
Get your feet wet, discover nature and a hint of luxury with this Maui itinerary.

Travel Tips and Practicalities

Fly into the Kahului Airport (OGG) to start your Maui adventure. Renting a car will permit you to explore all corners of the island with general ease. If you’re planning on traversing the scenic roads, consider renting a convertible and make the act of driving just as fun as the stops along the way.

This itinerary suggests five days to give you time to be active with time to relax beachside, though if you have the time, we do suggest extending your trip to accommodate more activities or visit other Hawaiian islands.

RELATED: 7 Reasons to Visit Hawaii This Year (And When To Go)

Where to Stay

Stay beachside at the Westin Maui Resort & Spa, Ka’anapali, and select either an oceanfront or mountain view room with a private balcony. There is a waterfall cascading into a koi pond complete with flamingos and swans viewable from the lobby. There are six pools and even a water slide. From the soft-sanded Ka’anapali Beach, the islands of Lanai and Molokai are visible. Snorkel and sunset cruises are just steps away. Try the mai tai from the restaurant by the pool.

There are numerous lovely hotels throughout Maui. Search hotel deals in Maui on TripAdvisor for additional choices.

Best Things To Do in Maui

Bask in the sun at your resort’s pool or beach area and beach hop Maui’s many top beaches. Nearly any water sport you fancy is possible in Maui from snorkeling, diving, surfing, paddleboarding, kayaking, canoeing, windsurfing, to parasailing. Dive down and discover the underwater world, reefs, and varied sea life. Swim with turtles at Turtle Town. Hike in volcanic craters, through bamboo forests, to waterfalls, along beaches, and up mountains.

Golf at one of Maui’s premier golf courses. Admire bird’s-eye views of the island by soaring into the sky on helicopter tours. Relax on a sunset cruise, or attempt to spot whales on a whale-watching cruise.

Where To Hike on Maui | The Best Things To Do in Maui Hawaii
Hiking is a great way to immerse yourself with nature on Maui and discover dozens of incredible viewpoints.


No trip to Maui is complete without a trip to Haleakalā National Park. There stands a dormant volcano that forms more than 75% of Maui. It rises 10,023 ft. above sea level, but 19,680 ft. of the mountain is under the ocean. As described by the National Park Service, “[t]his special place vibrates with stories of ancient and modern Hawaiian culture and protects the bond between the land and its people. . . . [R]enew your spirit amid stark volcanic landscapes and sub-tropical rainforest with an unforgettable hike through the backcountry.”

The crater is 2,600 ft. deep, two miles wide, and nearly seven miles across. If you’re going for sunrise (as many do), check the times for sunrise and then subtract a buffer. Note that guided sunrise hikes are offered to the top of the park, as are self-guided bike tours. Anticipate strong winds and a significant drop in temperate up at the crater. While it may be bathing suit weather down by the beach, bring at least a wind jacket on the crater. If you plan to hike in this desert landscape, you will want to be dressed for cooler temperatures. Even if hiking isn’t your thing, still drive up and admire the view.

Return down to hot, humid, and frequently rainy weather and hike Pipiwai Trail to Waimoku Falls, a waterfall that cascades down 400 feet. The path to the waterfall takes you through a dense and enchanting bamboo forest.

The Best Things To Do in Maui Hawaii
Looking up through the bamboo forest. Image courtesy Lenore Parr.

Waihe’e Ridge Trail is an excellent hike into the West Maui Mountains offering expansive panoramic views of both mountains and sea (so long as the clouds don’t sneak in obstructing your view).

Hike over remnants from Maui’s last lava flow at La Perouse Bay. Wear sturdy, closed-toe shoes as its very rocky and many are sharp and jagged.

The Best Things To Do in Maui
One of the most popular things to do in Maui is visiting its many black sand beaches.


Road to Hana

Virtually the entirety of the ~64-mile Hana Highway that connects Kahului with the town of Hana in east Maui is through lush tropical rainforest. It’s a narrow road with curves and ~59  bridges, most of which are one-lane-wide for two-way traffic. Start the drive early as there are many places to sightsee and hike along the way. It’s typically a full-day adventure. If you’d rather sit back and soak in the scenery without worrying about navigating the tighter turns, you can book a tour to do the trip for you.

Honokalani Beach

A remote black sanded beach contrasted by turquoise waters and surrounding greenery at Wai’ānapanapa State Park; Pipiwai Trail that takes you to Waimoku Falls; Ohe’o Gulch known as Seven Sacred Pools; and Wailua Falls are just a few of the must-see stops. Pre-download (since you can expect to lose cell service) an audio tour of the Road to Hana for local tips allowing you to make the most out of the drive without missing anything.

West Maui Circle Drive

While the Hana Highway tends to be the most popular for its spectacular scenery, many may find the views along the less-traveled West Maui Circle Drive to be even more incredible. Twisty and narrow roads passing over steep cliffs with few guard rails make this route intimidating. This route is not for the faint of heart and should only be taken by those confident in their driving skills. If time permits and you are, give both drives a try.

Winetraveler Tip: Be prepared for windy narrow roads around cliffs, and thus the drive time will be longer than expected. Be cautious and don’t speed.

Iao Valley State Park

Visit the Iao Valley State Park to learn about the history of the area and witness the lush tropical flora and the recognizable landmark, the Iao Needle. This “needle” that appears to be an emerald green spire was formed by a volcanic remnant that is now densely covered in vegetation.


Enjoy a delicious Hawaiian meal with signature cocktails while being swept away by a traditional Polynesian Lu’au experience at Wailele Lu’au that includes vibrant costumes and fire-knife dancers. It is located at the Westin Maui Resort and Spa’s Aloha Pavilion. For those staying at the hotel, don’t feel guilty about drinking that extra mai tai since you can walk back to your room.

Note that the Marriott Beach Resort offers an equally great Lu’au experience that that tickets can be purchased for in advance. The Sheraton Maui also offers great nighttime Lu’au show. You can grab tickets for that right here.

Helicopter Tours

Maui view by helicopter
Experiencing Maui by helicopter is a must-do for anyone visiting the island.

Several companies offer helicopter tours over the island of Maui, which we highly recommend if you’re willing to spend a bit more for a very unique experience. You’ll get to follow along some of the flight paths and take in scenery that was featured in movies like Jurassic Park. For any of the tours below, use code WINETRAVELER15 for 15% off any tours booked through our website. All these tours are highly-rated by our readers.

West Maui and Molokai Special 45-Minute Helicopter Tour

Experience the magic of Maui from a new perspective with an exclusive helicopter tour offered by Air Maui Helicopters that takes you soaring past hidden waterfalls, lush valleys, and ridgelines that are inaccessible by land. Witness the rugged beauty of the West Maui Mountains as you fly over rainforests, deep valleys, and rugged terrain that has been shaped by millennia of volcanic activity.

Cross the channel to neighboring Molokai, and witness the awe-inspiring vertical sea cliffs that spill 4,000 feet to the turbulent shoreline below. Get up-close views of a part of the world that has barely been touched by man, with an expert personal guide providing fascinating insights into the area’s history and geology.

With excellent narration throughout the tour, you’ll learn about the fascinating history of Maui and Molokai and the geological forces that have shaped these breathtaking landscapes over time. From the comfort of your helicopter, enjoy bird’s eye views of the island’s most iconic sights, including towering peaks, lush valleys, and crystal-clear waters that are teeming with marine life.

Doors-OFF West Maui and Molokai Helicopter Tour

Get ready for the ultimate adventure as you soar above the stunning landscapes of Maui and Molokai on this thrilling doors-off helicopter flight (also operated by Air Maui Helicopters). Feel the cool island breeze in your hair as you take to the skies and get up close to some of the most breathtaking sights you’ve ever seen.

Glide above towering waterfalls, sparkling rainbows, and lush valleys that are thick with rainforest, taking in the natural beauty of these stunning islands from a unique and unforgettable perspective. This is the only doors-off helicopter flight on Maui, offering unparalleled views and photo opportunities that you won’t find anywhere else.

Without the glare of windows, you’ll be able to capture incredible photos with your cell phone, making sure that you can always remember this once-in-a-lifetime experience. From the circular rainbows to the cascading waterfalls, every sight is more amazing than the last.

See The Reefs Underwater on a Submarine

Marine life up close on a submarine tour in Maui
Maui is one of the world’s best destinations to experience sea life up-close, with its crystal-clear waters and unique submarine and diving opportunities.

Atlantis Adventures Hawaii offers a bucket list experience unlike any other. Immerse yourself in an incredible underwater adventure on this Maui Atlantis Submarine tour. Descend more than 100 feet (30m) in an air-conditioned submarine, where you’ll experience the sights, sounds, and scenes of life beneath the waves. From colorful coral reefs to exotic marine creatures, this is an experience that you won’t want to miss.

Note that all Winetraveler kiddos must be 36″ or taller to ride the submarine. Keep your eyes peeled for seasonal whale watching and other wildlife sightings, adding to the excitement and wonder of this unforgettable journey.

The tour also includes a return shuttle cruise to the submarine dive site, giving you the chance to take in the beauty of the surrounding coastline and the crystal-clear waters of Maui. With morning and afternoon departure times available, this is a flexible and convenient way to explore the wonders of the deep sea.

Scuba Diving

Maui scuba diving
For those looking to get better acquainted with the remarkable underwater landscape of Maui, scuba diving is an ideal option.

Scuba diving in Maui is a bucket list activity that travelers should definitely consider when visiting the island, as it offers an unparalleled opportunity to explore the vibrant underwater world surrounding this tropical paradise. Maui’s crystal-clear waters and diverse marine ecosystems provide divers with the chance to witness an incredible array of marine life, including colorful coral reefs, exotic fish, sea turtles, and even sharks, in their natural habitat.

The island boasts numerous dive sites that cater to divers of all skill levels, from beginners to experienced enthusiasts. Some of the most popular dive spots include Molokini Crater, a partially submerged volcanic crater teeming with marine life, and the Cathedrals off the coast of Lanai, where you can explore stunning underwater lava formations.

Dive operators on the island offer various scuba diving packages, including guided tours, certifications, and equipment rentals, ensuring a safe and memorable diving adventure for all. You can book a dive excursion in Maui below. We include several that cater to different skill levels whether you’re certified or not.

Maui Scuba Diving Introductory Lesson from Lahaina

Embark on this 3-hour introductory scuba diving lesson in Maui offered by Extended Horizons Scuba, perfect for those who have always wanted to explore underwater but need a little guidance. Under the supervision of a professional instructor and in calm, protected waters, you’ll learn the essential skills for scuba diving. With a small group of just four divers, you’ll receive one-on-one attention as you master the basics on shore before venturing into the water. As you dive in the shallow waters off Maui’s coastline, keep an eye out for green sea turtles and other marine life inhabiting the coral reefs. This lesson is ideal for first-timers or those seeking a refresher. Please note that flying within 18 hours of scuba diving is unsafe and not permitted.

2 Tank Lanai Cathedral Dive

For certified and more experienced divers, Dive Maui offers a unique and unforgettable adventure to the neighboring island of Lanai for a 2-tank dive in the ‘cathedral.’ Join a small group of fellow scuba divers as you explore an underwater world filled with caverns, arches, lava shoots, and swim-throughs.

With depths of up to 85 feet (26 meters), you’ll have the opportunity to observe several species of wildlife, including dolphins and whales, making this an experience not to be missed. Take in the stunning views of Maui and Lanai from the boat and enjoy the calm, clear waters that make this dive site one of the best in the world.

If you opt for a morning dive, you’ll have the chance to witness more wildlife activity, adding to the excitement of this already amazing adventure. Between dives, you’ll be able to refuel and recharge with a delicious lunch and snacks, making sure that you’re ready for whatever the next dive has in store.

Small Group Shark and Turtle Dive for Certified Divers

For the more adventurous and brave Winetravelers among us, there’s an unforgettable experience waiting in Maui. Ideal for those interested in shark and turtle encounters, this experience also offered by Dive Maui takes certified divers on a small-group dive to explore a condemned pier that has transformed underwater into a vibrant reef.

Follow your experienced instructor through the pier wreckage, searching for sea turtles and reef sharks that have made their home there. But that’s not all – the sunken pier is also home to large schools of fish, octopus, eels, nudibranchs, and the elusive frogfish, making this an incredible dive for any experienced scuba diver.

Don’t worry about packing your own gear – all scuba equipment is provided, allowing you to focus on the stunning underwater world that awaits you. This small-group dive offers a more personalized experience, ensuring that you get the most out of your adventure and create unforgettable memories that will last a lifetime.

Whale Watching with an Open bar

Whale watching in Maui
Watching a Humpback whale breach in Maui should definitely be on your itinerary. We were lucky enough to see a double breach on our last trip to the island.

Whale watching is an unforgettable and must-do activity on Maui, providing visitors with the unique opportunity to witness majestic humpback whales in their natural habitat. Set sail from Ka’anapali Beach on a 2-hour whale-watching cruise with Sea Maui, that also just happens to include an open bar, an experience perfectly tailored for the Winetraveler.

As you venture into one of the world’s most active whale playgrounds, a knowledgeable naturalist guide will provide fascinating insights into the whales’ migratory patterns and behavior. Aboard the spacious catamaran, you’ll find ample seating options, including bean bags on open nets, allowing you to get up close and personal with these incredible marine mammals. To enhance your experience, enjoy unlimited drinks from an open bar as you cruise alongside the awe-inspiring humpback whales. This family-friendly adventure departs directly from Ka’anapali Beach, immersing you in the rich marine life off the coast of Maui and creating memories that will last a lifetime.

Maui Wine

Taste local with a visit to MauiWine while breathing in the mountain air. They cultivate 6 grape varietals: Syrah, Malbec, Grenache, Chenin Blanc, Viognier, and Gewürztraminer. As stated on their website, their “vines thrive in the fertile volcanic soil, nurtured by crisp mountain air and long growing season.”  

Book or Plan a Trip To Maui

We’ve already mapped out your entire trip to Maui. What are you waiting for? Take the trip! Feel free to ask any questions in the comments below.

Frequently Asked Questions about Visiting Maui

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