5 Day Maui Itinerary & Travel Guide: The Best Things To Do

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 travel guide.

Travel Tips and Practicalities

Fly into the Kahului Airport (OGG) to start your Maui adventure. Stay updated on the constantly changing travel requirements. Go to Go-Hawaii for useful information. Presently Hawaii’s mandatory 10-day quarantine can be bypassed by a negative COVID-19 test before departing (but always double-check before leaving). Book fully refundable accommodations and/or fares whenever feasible.

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.

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.

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.”  

Things To Do

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.

Hikes

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. 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.

Drives

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.


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.

Lu’au

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.

Book or Plan a Trip To Maui

We’ve already mapped out your entire trip to Maui. Book or follow along with this itinerary through Winetraveler or share it with your friends! Feel free to ask any questions in the comments below.


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ABOUT THE AUTHOR

Lenore Parr is a commercial bankruptcy attorney and stay-at-home-mom with a passion for adventurous and family-based travel with her husband and children (4yo and 1 yo). She has traveled with the kid(s) to 34 states and 23 countries.

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