Hawaii Itinerary: How to Spend Three Days on Maui

It seems a lot of people in our networks question whether it’s worth the effort to make big trips if you don’t have at least a week to dedicate to traveling. That has never been our philosophy, mostly because Brian has never had much vacation time. If we only traveled when he had accrued an entire week off, we’d rarely go anywhere.

Instead, we’ve tried to jump on travel opportunities wherever we can find them – planning around holiday weekends where we have a bonus day off, leaving for trips after work on Fridays to jump start the next day at the place we’re headed, extending work trips where we’re already at a destination, etc.

And maybe more important than these logistical considerations is our overall travel philosophy: embrace that you can never see or do everything at a destination in one trip, no matter how long it is, so experience what you can, when you can!

That was certainly our sentiment planning a three-day trip to Maui. Disclaimer: Our trip was technically four/five days because we flew to Maui after work on a Friday night and flew back to Seattle on Tuesday morning. So this three-day itinerary is what we accomplished on the three full days we were on the island v. the travel-only days.

The Safe Travel Hawaii program was in full swing as we planned our trip so we had lots of pre-work to make sure we met all of the criteria to get our green check marks and pre-clear status ahead of time. I see the program is ending March 25 given the decline in COVID-19 numbers (yay!) so I won’t detail the process here. If you have specific questions, feel free to let me know in the comments – I’d be happy to share our experience.

How to Spend Three Days on Maui – Itinerary

Day 1: Drive the Road to Hana

We arrived late Friday night, spent the night in Wailuku near the airport, and then woke up early on Saturday to spend a full day on the Road to Hana, making lots of stops along the way (I wrote about our favorite stops in this post).

For us, dedicating the full day to the drive and spending the night in Hana made sense because it set us up perfectly for day two.

Day 2: Drive the Pi’ilani Highway and Explore Haleakalā National Park

We spent a good portion of day two driving the Pi’ilani Highway, also known as the back side of Haleakalā drive. Along the way we hiked in Haleakalā National Park, enjoyed waterfalls and old lava fields, and even visited aviation pioneer Charles Lindbergh’s grave (I detail all our stops in this post).

We arrived back in upcountry Maui in the early afternoon where we had a late lunch, visited Maui Wine, checked into our AirBnB in Kihei, caught the sunset from Makena Beach, and grabbed dinner and a sampler at Maui Brewing Company (for things to do in Kihei, check out this post).

We turned in early because we needed as much sleep as possible before day three!

Day 3: See the Sunrise in Haleakalā National Park and Visit West Maui

A standout moment in our Maui adventures was watching the sunrise from 10,000 feet in Haleakalā National Park. We set out around 3:30 a.m., experienced the sunrise, hiked the Sliding Sands trail into the crater, and spotted some wildlife (details about our morning adventure in this post).

After we were done hiking we grabbed brunch at Kihei Caffe, took a quick siesta, and then drove to West Maui for the afternoon. While Lahaina wasn’t our favorite place, we did learn a lot about the history of that whaling city and the island’s sugar plantation past, and we enjoyed sunset and one of the best meals of our trip (to learn where, check out this post).

Bonus! Departure Day: Food and Farewell

Our final morning in Maui we hit the beach across the road from our AirBnB in Kihei, shared our first-ever taste of dry mein at Tin Roof in Kahului, shared our first-ever spread of spicy fried poke from Like Poke at a food truck park near the airport, and then waddled our tired and delightfully full selves onto the airplane for our late morning flight home.

It was a whirlwind three days on the island. Of course we could have done more – or slowed down the pace of what we did – if we’d had more time. But if we’d waited until then, this trip might not have happened. I can’t say I have any regrets squeezing in this quick trip and all of the incredible experiences Maui has to offer!

2 thoughts on “Hawaii Itinerary: How to Spend Three Days on Maui

  1. Great post and wonderful photos. I’ve never been to Hawaii but would very much love to visit one day to see its many sights and attractions in person. Thanks for sharing and have a good day ☺️ Aiva

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