A Five-Day Maui Adventure Itinerary

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To be honest, I never really considered Hawaii until I received a destination wedding invitation from some of Ty’s closest friends. “Come join our celebration in Maui, Hawaii,” I read aloud from the save-the-date. Of course, we knew we wanted to scratch the state off our list, but I didn’t think it would be so soon. To me, Hawaii was not a place 20-somethings went seeking adventure - unless you consider finding the bottom of a Mai Tai an adventure (which I do).

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But boy, do I love being wrong. After spending around five days in Maui, the island is officially tucked into my “Places That I Love & Have Completely Caught Me By Surprise” folder. All of my predispositions about the island being a potential tourist trap were gone in mere hours after stepping off our plane. Mountains were flanked on either side by sparkling blue ocean. Beat up pickup trucks were the ride of choice. Chickens belonging to no man skirted across the road at their own pace. 

Our Maui Adventure Itinerary

To start off, our itinerary was pretty loose. We knew of some stops and must-sees on the island, but that didn’t dictate exactly how we spent our day. That mindset worked in our favor, especially during our day on the Road to Hana or Hana Highway. With so many stops along the way, we made a full day out of simply doing whatever the hell we wanted.

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Day 1: The Road to Hana & Haleakala National Park

Swimming holes, bamboo forests, and waterfalls

We rose early the next day to grab the sunrise views at Haleakala National Park in the Summit District; yet somehow, not early enough. We were met with a long line of cars that left me convinced we weren’t going to catch the sunrise in time. But, as chance would have it, we found ourselves taking the trail less traveled and were treated to a better view than we could’ve possibly imagined.

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Day 2: Haleakala National Park: Summit District

Biting winds, gorgeous sunrises, and a surprise proposal

Our remaining days were spent in a combination of elated stupor and “why-didn’t-we-book-a-longer-stay” regrets. We spent our energy on a series of mini adventures, including hiking within Iao Valley, attending the most beautiful wedding ever, and saying hi to sea turtles and fish while wrestling with a snorkeling mask.

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Day 3 - 5: Kihei and Lahaina

Beaches, tourist traps, and sea turtles


The end of our trip was met with a sadness I hadn’t experienced since I left Denali in 2012. Although our stay was much shorter than our excursion up north, I was just as convinced that we could spend a few good years bouncing between the Hawaiian Islands and never run out of things to do.