Chasing the Sun: A Run-derful Evening Aboard the Pride of Maui Sunset Cruise and Luau

With a direct flight from PDX to Maui, we love heading to the island with the family as a last hurrah to summer. We have been a few times over the past half decade or so and have always enjoyed getting out on the water for some sort of excursion. We have done snorkeling a few times, including a great time with the Pride of Maui back in 2019.

Make a Day of It: Kicking off a Runcation with the Pride of Maui

In late August, we headed back to Maui and turned to the Pride of Maui again – this time for their Maui Sunset Dinner Cruise & Maui Luau.

Read all our Make a Day of It Features here!

 

First, the Running:

The Pride of Maui docks at Maalaea Harbor, and what better way to unwind before a warm sunset than with a few miles of beach running?

Maalaea Beach offers a beautiful, uninterrupted stretch of sand that’s perfect for running. An out-and-back route covers around 3.5 miles—quite impressive. If you’re up for more, you can double back for additional miles. However, running on Hawaiian sand can be quite challenging, so be prepared to feel pretty wiped, regardless of how far you go!

If you need a break from the sand, take a short detour about half a mile in (or at mile 2.9 on your way back) to the Kealia Coastal Boardwalk. This boardwalk offers a scenic 0.8-mile out-and-back route for a change of pace.

The Experience:

Man, what a time. There’s something truly magical about Maui’s warm summer sunsets. We make it a point to head to the beach each evening to watch the stunning colors as the sun dips below the horizon. I almost get emotional just thinking about it. Adding a Pride of Maui Sunset Cruise to the mix takes the experience to an entirely new level.

Right off the bat, I want to highlight just how amazing the staff at Pride of Maui are. They’re incredibly chill and down-to-earth, providing a truly welcoming experience. This can make or break an outing, and the team here really excels.

Our excursion began at 530 pm as we set sail into Maalaea Bay. We were treated to live music from Hawaiian guitarist Kekoa, who has performed across the Hawaiian Islands and around the world for over 30 years. It was nothing short of incredible.

Dinner and drinks were surprisingly bountiful and tasty for being on a literal boat. We enjoyed a tropical luau-style buffet with a variety of appetizers and entrees. My wife indulged in some delightful tropical cocktails, while I opted for an IPA from Maui Brewing—keeping in mind from past experience that a single beer is about my comfort level with the waves.

Luau experiences can be pricey across the island (though they’re often worth it at least once), so having a small, intimate luau on the Pride of Maui felt both special and fun. They fill their boat to only 60% capacity to allow for space and intimacy. We were captivated with their Polynesian dance performances and shared insights into ancient Hawaiian folklore and culture. Experiencing a luau on a sunset cruise made this perhaps the most memorable luau we’ve ever attended.

As the sun dipped below the horizon and we headed back to shore, our little family couldn’t stop marveling at how incredible the experience was. We wholeheartedly recommend this excursion to anyone—the Pride of Maui truly knows how to create a memorable adventure.