Pride of Maui Sunset Cruise: Serving Up Mai Tais & Magic

Pride of Maui Sunset Cruise: Serving Up Mai Tais & Magic post thumbnail image

Share325Pin133Tweet458 Shares

You won’t often hear me refer to things as must-dos in Maui. I mean, it’s all subjective, right? Diff’rent strokes for diff’rent folks!

But then again…

If you love sunsets, boat trips, live music and adult beverages…

You MUST try a Pride of Maui Sunset Cruise. MUST!


I’m no stranger to the Pride of Maui; I’d been on a wonderful whale watching tour a year or so prior and couldn’t say enough good things about the company or how the tour was run. The staff worked their butts off to ensure a smooth ride, and did it with huge smiles on their faces the whole time.

Our experience on the sunset cruise was no different!

I decided to bring my friend Kristen along with me this time and we were excited by the opportunity to get a little dressed up for a change. Island life is fairly casual, and living in Maui doesn’t provide many opportunities for dresses and nice jewelry–at least, not upcountry where we live!

We threw on some complementary stripes and even matching sandals, but I swear we didn’t coordinate.

Great minds really do think alike.

Pride of Maui cruises depart from Maalaea Harbor, located roughly halfway between Kahului and Lahaina. According to every tour I’ve ever taken from here, it’s the second-windiest harbor in the world!

Since it was March and technically still winter (and whale season!), we brought along jackets just in case, since the temps could often drop pretty significantly after sunset. Thankfully we didn’t end up needing them, but I’d always recommend you bring one to protect you from wind, the sun, or both.

A Pride of Maui sunset cruise includes an open bar as well as dinner and dessert. We boarded around 5 pm with group of maybe 40-50 people, leaving plenty of space for us to move around on this sturdy catamaran and take in the views from every angle.

The tour lasts 2 hours, from 5:30 pm to 7:30 pm. It’s essentially a floating, open-air cocktail party complete with island sunsets, live music, and even some cultural dances for after dinner entertainment.

Of course, like most other passengers, we kicked things off with a round of cocktails. Mai Tais seemed like the right thing to do, so we started there. Other drink options include local beer and wine selections as well as more tropical cocktails (Lava Flows, Piña Coladas and the like) and premium vodka, gin, whiskey and more.

While I can’t say it was the best Mai Tai I’ve ever tasted, I appreciated the fact that they were served in compostable cups.

After grabbing our first round of drinks, we made our way to the bow of the boat to look for whales. It was the very tail end of whale season, but we remained hopeful–and we were not disappointed!

Just a few moments after wandering outside, whales began popping up all around us. There weren’t any spectacular splashes or breaches, but lots of round backs coming out of the water, and a few flukes for good measure.

Later in the evening we did catch some breaches from a distance, but those first sightings up close were really special. They always are!

Whale season lasts from November to March. It’s probably my favorite time of year just for the pure magic of seeing such enormous, majestic creatures up close. You don’t need to take a boat tour to see them, either. You can watch whales breaching from shore every single day through the winter.

We couldn’t bear to pull ourselves away from the bow as long as the whales continued to play nearby.

After awhile, a kind stranger approached us asking if we’d like to have our picture taken together for a change–of course we said yes!

We soon found out this kind stranger was also our entertainment for the evening–a musician playing classic hits on the guitar, keyboard and harmonica.

We chatted for awhile and then headed inside to enjoy some of his music near the bar area.

We made sure to visit the back of the boat (stern, if we’re speaking proper boatsman) to enjoy the view of Maui as we cruised in the opposite direction, into the open blue. The West Maui Mountains captivate me every single day–they are the first thing I see when I look out my window in the morning.

But seeing them from the water is an experience unto itself! I’m telling you, I’ll never get tired of taking in this island from every angle imaginable.

Dinner was served about 45 minutes into the trip, and included a buffet of delicious, freshly-prepared food. I had made sure to call ahead of time and request a vegetarian option, per their instructions.

Non-meat choices included some grilled veggies, fruit, crackers, cheese, yummy artichoke dip, and some mini tartlets. It was plenty for me, but if you’re vegan I’d make sure to let them know (just call the reservation line at least 24 hours in advance of your tour) so they can provide you with something more substantial.

All dietary needs can be accommodated, but you do need to arrange it in advance.

Following dinner and as the sun was finally beginning to set, crew and passengers gathered on the top deck for some true Hawaiian entertainment. There was dancing, there was chanting, there was audience participation. We had a ball!

The sun finally dipped below the horizon as we made our return to Maalaea Harbor, and it was time for one final dance party on the lower deck.

We grooved until the very end of the trip, soaking in every last moment aboard the Pride of Maui. We’re couldn’t have loved the experience any more and we’re already looking forward to our next cruise!

Sunset cruises are just one of the many options the Pride of Maui offers. Check out the full list here!

Many thanks to the Pride of Maui for hosting us on this incredible journey!

Leave a Reply

Your email address will not be published. Required fields are marked *

Related Post