Trilogy Sunset Dinner Cruise, Maui, Review – Trilogy Excursions

Getting out on the water at sunset is possibly one of the most romantic and incredible things you can do on your Maui Vacation. The Maui coastline is one of the most scenic in the world and viewed from the water during the magical hours of sunset it is a spectacle most will remember for a lifetime. So getting out on one of Maui’s many Sunset Cruises is highly recommended.

However, there are a lot of companies offering a lot of different experiences. Most of which have their own unique pros and cons. We detail these cruises in our Sunset Cruise Guide here. One of our favorites though is the Trilogy Excursions Sunset Dinner Cruise. This cruise ticks all the right boxes for us, so we took a recent trip to see how the company is getting on post-pandemic and to bring you a full Trilogy Sunset Dinner Cruise, Maui, Review.

Trilogy Sunset Dinner Cruise
  • Price
  • Food
  • Drinks
  • Vessel
  • Overall

Disclaimer – This is not a paid article, all opinions within are entirely our own and not in any way sponsored by Trilogy or anyone else. We paid for the trip entirely with our own money and made sure we did not announce our presence. We just visited as paying customers to see how things went down. Affiliate Links – there are some affiliate links within this article, and if you book your tour through these links then we d receive a small commission to support the site. This does not affect our review, however.

Booking Options

Trilogy Sunset Cruise

Sunset Dinner Cruise – Lahaina – Ma’alaea – $162

The trip we booked sails from Lahaina but Trilogy also offers the same cruise out of Maalaea too. These are both very similar options and really the most important deciding factor is where you are staying. If you are staying in West Maui, the Lahaina trip is better, if you are staying in South Maui the Ma’alaea Trip, is simply due to proximity.

Sunset Cocktail Cruise – Lahaina – Ma’alaea – Kaanapali – $117 Adults – $74 Kids

The other option offered by Trilogy is the Sunset Cocktail Cruise. This is very similar to the Dinner cruise but offers light bites and cocktails only rather than the full sit-down meal. It is also a little shorter at 2 hours. This cruise tends to be a little more lively and does allow children, whereas the Dinner cruise is more romantic in nature.

Along with Maalaea and Lahaina, Trilogy runs this cruise out of Kaanapali too so if you are staying around that area you can stumble from the boat afterward and back to your hotel!

You can read about the different Sunset Cruises in Maui here, but for the rest of this article we focus on the Dinner Cruise, but the Cocktail cruise is very similar just with less food.


Trilogy sunset Cocktail Cruise

The Pre-Boarding was a little chaotic really. The main issue is there is no booth or kiosk at the boarding location. This means there is no person to talk to, all you have is a Sign. While this clearly states this is the Trilogy Boarding area, there is no other confirmation. Trilogy does not have a permanent birth at this location, but pulls in and loads and unloads, like most other cruise companies using the dock. So there wasn’t even a boat docked to show we were at the right spot.

We just had to put faith in the sign being right and that the large group of equally confused people were also in the right spot. It didn’t help that most other cruises operating out of here seemed to have assistants happily corralling their guests and getting them aboard. We simply had a sign.

Sure enough though, just before our boarding time, the Trilogy catamaran sailed into the harbor and moored up at the dock. The captain then quickly came over to begin the check-in process. This was swift and simple and consisted really of just taking your names. We were then escorted to the vessel where boarding began.

The Vessel used for these tours is one of Trilogy’s 6 custom Sailing Catamarans. These are equipped with individual tables so you are not seated with random strangers and have somewhere designed to sit rather than having to perch in a free corner as we have found on some boats. It’s a nice layout and is perfect for the dinner cruises on offer. Seating seemed to be based on who checked in first! We were amongst the first to go a nice seat right at the front of the boat with excellent views.

The personal tables are great as they give couples the privacy they might want, however, they are also close enough to other people that you can happily chat amongst yourselves too. We love getting to know our new crew mates for a couple of hours, especially after the 3rd or 4th round of drinks! It is kind of the best of both worlds in this respect.

Cruise Route


The route for this cruise does not really go anywhere. We pulled out of the harbor and the crew then killed the engines and we floated peacefully just outside the harbor, a little worried that was it! However, this was just for the mandatory safety briefing and a little info on the itinerary.

After this, the first drinks arrived and we got underway on the sail. For this trip, we simply headed a little way up the coast towards Kaanapali, before tracking quite far out into the channel and then back in the other direction, south past Lahaina, near Olowalu, before looping back towards the harbor.

Essentially what the captain is doing is just spending time on the water as the sun sets over the stunning coastline. The particular route will normally be decided by conditions to give you all the smoothest and most enjoyable ride, and partially dictated by the wind, which leads us onto…

Does Trilogy Cruises actually Sail?

Sails Up!

Not all of these tours actually use the wind to power the vessels. They use images in their promotions of sailing and phrases like they try and use the wind where possible. But on the whole, they usually just plod along under engine power. It’s much easier and the vessels can pretty much go where they like.

Trilogy however REALLY does try its best to get the sails up and power along under wind power. The modern Diesel engines on these boats are really quiet and unobtrusive, but there really is nothing like cutting the power and just silently cruising along with the wind in your sails. It’s just so utterly calm and peaceful out there without the engines running.

On our trip, the engines were killed really early and the sails put p for the entire duration of the trip, even before we got our first course! We even performed some tight tacks (turns) and other maneuvers.

Of course, there are no guarantees, but you can be fairly sure if the wind is suitable, the Trilogy crews pull out the sheets!


The food on offer was pretty decent considering it is to be served from a pretty small and basic galley. We can’t as it was the best meal we had on the trip, but it wasn’t the worst. As soon as we were seated we were served some excellent bread sticks with lilikoi (Passion fruit) Butter. These were really good, still warm, and perfect with the sweet lilikoi butter. A bit like the Olive Garden Breadsticks we could have just eaten these all day!


Smoked Salmon on Crispy Pita with fresh dill

Cucumber Cup with Maui Onion Cream Cheese

Tataki-Style Beef Tenderloin Crostini

The Starter Course was served just after the sails were raised and we were cruising along under the power of the wind. The Appetizer course is a trio plate of small Hors d’oeuvre, as opposed to a choice of course.

The Smoked Salmon was really nice and reminded us of the Sashimi Pizza we recently tried in Las Vegas, which cost us rather a lot more than this! The Beef Crustini was also pretty good with a large chunk of beef. The Cucumber cup was less exciting, basically a slice of cucumber with some cream cheese on it.

Overall the Course served its purpose as a tasting plate and a warm-up to the rest of the meal.


Caesar Salad with Blue Cheese Vinaigrette

The next course was more forgettable. This was a large amount of bland lettuce, with a very sweet shop-bought dressing, and a couple of croutons. Honestly, we could have just done without this course at all and just considered it a 3-course meal. However, if you were to count the Bread-rolls as a course, then we are back to 4!

Main Course – Choice of

Seared Top Sirloin Steak with herb & garlic crust

Fire-Grilled Chicken with citrus & thyme

Fresh Island Fish, panko-crusted with lemon caper butter

Pasta Primavera with Portobello mushroom & sauteed vegetables in fresh marinara with basil

Unlike the other courses, this main is a choice of one of the 4 options, essentially Chicken, Fish, Steak, or Vegetarian. A quick straw poll saw the Steak easily the most ordered item, but we hedged our bets and ordered a Steak and the Fish.

The steak was really good, at least considering the constraints of the kitchen. It was still nicely pink and juicy, with some decent flavor, the vegetables on the side were a little bland, but the meat made up for this. The Fish on the other hand was disappointing. It claimed it Panko-Crusted but it was more “soggy breading” and there was little in the way of flavor. Out on the ocean, you can early appreciate good seafood, and unfortunately, recognize less than great.

We saw the chicken served to other guests and this looked good too but we did not catch sight of the pasta. Overall, if you stick to the chicken or the steak you will have a good meal, and hopefully, the vegetarian option is pretty good as well…but avid the fish


Lilikoi Cheesecake

Fresh Island Fruit

Dark Chocolate Truffle

The final course was served well after the sun had set as we sailed along on the dark ocean with the stars sparkling above. It was not a mesmerizing desert but it was pretty perfect for the setting and meal. The Truffle was really nice and the fruit was a nice tropical touch. The cheesecake had a little too much base but was nice enough.

Dietary Restrictions

The menu is pretty set, unfortunately. There is obviously a Vegetarian option for the Main, but the appetizers are set and only some of the options are suitable for Vegetarians, and hardly anything really Vegan Friendly. We are sure you could ask for more breadsticks to help fill up on and, TBH they were really good!

We were quizzed intently about dietary restrictions and allergies on arrival, but it’s always best to contact the company ahead of schedule if you have any allergies so they can advise you beforehand on what options you may have.


The Drinks were a real highlight of the cruise. Trilogy operates an open bar on this tour and the drinks really do flow pretty much as expected…constantly.

There was a bit of a lull after our first drink, which was served just after leaving the harbor. We really struggled to get our second, which kind of led us to believe the service might be artificially restricted by slow service, but once we got our second, the refill rate jumped right up to the “never an empty glass” rate. Which is our preferred rate. Drinks were also served right up until the vessel entered the dock. Here any unfinished drinks were collected (or quickly downed) as it’s against regulation to be serving drinks in the harbor.

One thing that stands out for the trilogy cruises is they show proper Barware in their promo photos which is nice, as we just feel like children when the drinks are served in plastic cups. Unfortunately, this is not quite as it seems as the barware is plastic, not glass. It’s still a huge improvement from cocktails in plastic cups, and it at least feels like you are an adult. We know breakages are a thing out to sea and we do understand the lack of glassware. The plastic barware s a good solution in our opinion. Not least as we hat the throwaway nature of disposable cups!

The drinks themselves were also pretty good. There were a couple of beers from Kona Brewing, a Sauvignon Blanc, Meiomi Pinot Noir, and prosecco, all of which were good quality, and a good selection of cocktails.

There was no Mai Tai which seemed a bit strange, but it’s not like we didn’t get plenty elsewhere. The standout drinks for us were the Captain’s Mule, a nice tropical take on the Moscow Mule, firey and quenching. The 808 Marg was a good marg and the Lahaina Sunrise was a great twist on the classic Tequila Sunrise. Finally, the inclusion of an old-fashioned to sip after the sun had gone down was inspired!

Overall we were very happy with the drinks service. For us, it’s a really important part of an experience such as this. We certainly got as many drinks as we would want and left the boat pretty merry.

Whale Watching and Wildlife

Molokini Snorkeling Humpback Whales

These tours are not promoted as wildlife spotting tours, but out on the placid waters of the Auau Channel, there is always a good chance of sighting some wildlife. Outside of Whale Season, there are abundant dolphins, turtles, flying fish, and even the chance of rare Monk Seals.

During Whale Season, well the odds of not seeing a whale are pretty slim! Whales really are every in the channel and, certainly, during the peak months, whales pop up all the time. Trilogy does not really go whale hunting, they simply cruise around as they usually do, however, this s 99% of the time enough to find whales.

Unfortunately, we were there at shoulder season, and most of the dolphins had moved away and the whales yet t arrive and we didn’t really see much out on the water. The best we got was once the darkness fell and we saw a huge amount of flying fish and needlefish darting away from the boat as we sailed by.



We had an absolutely fantastic time out on the water with Trilogy. The food would probably have been disappointing in a restaurant, but it was perfectly decent, and when you consider the number of drinks we received it was really pretty decent value. Dinner, Bottomless drinks, and a fantastic cruise watching the sunset over the seriously spectacular west Maiu scenery…it was a very rewarding experience.

To be totally honest, I am fairly easily pleased where boats are concerned. Stick me on a boat, out on the water and I am happy. Ply me with food and drink and the most stunning scenery in the world and I am very very happy! Kate is a little more demanding, she just isn’t as deliriously happy out n the water as I am. The tour has to be the right option for her, and Trilogys Sunset Dinner cruise really ticked every box.

The acid test was as we pulled into port and the crew mentioned it might be nice t leave a little tip for the crew. We are not natural tippers, it’s just not in our culture. However, we know the customs us different in America and usually begrudgingly get our hands in our pockets. However sometimes the crew or staff REALLY deserve it, sometimes they seem to have done everything to make your time special and a tip just feels the most just and natural thing in the world. This was absolutely one of those occasions and we gleefully gave the amazing crew a little extra for their service.


The cruise just hits all the right marks in our opinion. The food was good, the drinks flowed, and we love the assigned seating and personal tables. Any time spent on the water in Maui is very special but sunset is just the most magical, and the Trilogy Cats are really nice vessels to enjoy the experience from.

The highlight for us were the crew. They were really tireless and worked super hard to give us a great experience, The captain was seriously talented and super knowledgeable, I even learned a few things on this cruise, which I don’t often do anymore having been on the water in Maui so often now. Every effort was made to go sailing, and when we say that we mean 95% of the cruise was under wind power so they really couldn’t do much more!

It really was the perfect tonic to let us relax and unwind. The whole trip was just relaxing and peaceful. Mellow Island vibes on the speakers, refreshing cocktails on tap, and just the most incredible scenery imaginable.


There are loads of different options for dinner cruises in Maui. Trilogy is one of our favorites, but other options may suit you better. They are not necessarily better or worse just different.

The best place to weigh up all the options is our Maui Sunset Dinner Cruise page, or if you prefer the idea of a cocktail cruise you can read about those there. But on top of the Trilogy Cruises we also love:

Pride of Maui – Luau Sunset Dinner Cruise – Budget Option
Alii Nui Royal Feast Cruise – High-End Dining
Maui Princess – Large Elegant Vessel

Have Your Say

Have you been out on a Trilogy Dinner Cruise? How did toy find the experience? Did you think it was good value or an expensive tourist trap? Hopefully not the latter! Have you been on a different cruise or another kind of aquatic Maui adventure? Whatever your thoughts we would love to hear from you. Just fire away in the comments below. And as ever, if you have any questions we are happy to reply in the comments below.

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