Best Maui Sunset Dinner Cruise – Find your Dream Sunset Cruise in Maui

Hawaii is an Island Nation and an ocean fairing culture so naturally for visitors to Maui some kind of Ocean Cruise is a nearly essential part of any visit. There are plenty of options for getting out onto the water, Snorkel Cruises, Rafting Excursions, and Whale Watching Tours to name a few. One of the most civilized and indulgent is a Sunset Dinner Cruise. Fine Dining, hand-crafted drinks, Stunning Scenery and the stunning spectacle of the changing colors as the sun dips down into the Pacific Ocean.

There are so many options for cruises of this nature available on Maui and unfortunately, not all are created Equal. While you may be imagining a romantic sail with your significant other, enjoying a glass of bubbly and a divine meal, while the sun gently dips into the Pacific Ocean, the reality can be quite different as you are shoved onto a tightly packed deck with hundreds of other people for a mass-produced meal with a plastic cup of heartburn. Our guide to the Best Maui Sunset Dinner Cruise should help you sort the wheat from the Chaff and find the Best Sunset dinner cruise on Maui.

Maui Sunset Cocktail Cruise

Dinner Vs Cocktail Cruise?

These Dinner Cruises offer a high-end luxury excursion which on the whole do not come cheap. You get a 3-4 Course meal, often an Open Bar, and a wonderful cruise with some of the best scenery imaginable. However, if you are looking for something a bit more budget-friendly. You might consider a Cocktail Cruise.

These are very similar, but forgo the full-on dining experience, instead just offering Pupus (Apetser) and a great selection of drinks from their open bars. We love these for their low prices and shorter duration so you can get on and enjoy your evening further afterward. They also do not moor up so it’s a constant cruise with more scenery.

Take a look at these Cruises here as they are good options, however, we do like the fact that Dinner Cruises combine a meal out and a cruise all in one so there is no need to head to a restaurant afterward. And unless you head to MacDonalds, the difference in price between the full dinner options and the Cocktail cruises, would not get you much in most of Maui’s Restaurants.

Sunset Dinner Cruise Experience

Let’s just take a minute to have a look at what you can expect on a Maui Sunset Dinner Cruise. While the various cruises vary slightly they do all offer a fairly similar experience.

You will be required to check in around 30mins prior to your cruise, we recommend getting to the check-in point nice and early as seating can be first come first served. When boarding the boat be prepared you may be asked to remove your shoes. Not all Cruises do this but many do as it is Hawaiian custom to not wear shoes aboard.

You will be seated and normally served a welcome drink once the cruise gets underway. Most Dinner cruises steam or sail for a good distance along the Napali Coast offering stunning views of the west Maui Mountains while enjoying drinks along the way, you may be served an appetizer course on this portion of the journey or they may wait until the next section. If you are visiting during Whale Season then this will be the best chance for whales.

Most cruises will moor up while dinner is served. This allows a more stable dining experience without the interruption of rogue waves setting plates and chicken breasts flying! Even if your cruise does not moor, it will find a calm area and reduce the speed as dinner is served.

Most Cruises time the sunset to be around dessert and will usually serve an after-dinner drink. With the sunset the cruise will then head back along the coast, but this time as the light fades and the colors darken, the Stars will come out and the last few cocktails can be enjoyed under the stunning dark skies of Maui’s ocean.

Where do the Sunset Dinner Cruises Sail from?

West Maui Mountains

There are several locations these cruises sail from both in West Maui and South Maui

Maalaea Harbor

Maalaea Harbor is the main harbor on Maui’s Leeward Coast and is devoted mainly to tourist activities (as opposed to Kahului Harbor on the Windward coast which is mainly industrial).

The Harbor is nice and convenient, has lots of parking, and the boats can be boarded via the various slips and as such you can walk directly onto the vessel. You will see why we mention this below. For most people staying in South Maui, this is the most convenient location as if you were to drive to Lahaina, you would be driving directly past Maalaea.

Lahaina Harbor

Lahaina Harbor is much smaller but is equally well equipped and has a surprising amount of vessels sailing from it, including some pretty big boats which is surprising for such a small harbor. Parking is trickier as many of the free lots fill up early in the day, but there are paid options. This is the main choice for those staying in the West, like Maalea, most people in the west would need to drive right past Lahaina to get to Maalaea.

Kaanapali Beach

There are now many options on this list that depart from Kaanapali, the cocktail cruise sail from here more commonly but there are some cruises that leave from the beach. If you are not aware, there is no harbor or slip at Kaanapali, and as such the cruises leave direct from the beach. These are all smaller catamaran vessels and they literally beach themselves on the shore allowing you access via the fold-down steps. This means you will be in the sand and the surf so you will get sandy feet and long dresses may even get a little soggy.

It’s not ideal for a sophisticated dinner cruise, hence why most leave from the harbors, but it’s all good fun and if you don’t mind the grittiness then the ability to walk directly to the cruise from your hotel and then stagger back after enjoying the Open Bar is great.

Which is best? While on the whole Maalaea is the best for those in the south, and Lahaina for those in the west, the actual cruise and what is offered and how this fits your tastes is far more important than the departure point. So we

Getting to the Departure Point

There are plenty of parking options at all departure points, so driving is easy and convenient. However, we have mentioned SEVERAL times now these cruises often have open bars or at least some kind of included drinks, so the odds are when you get to shore no one is likely to be able to drive. Drink Driving is not appreciated in Maui and punishments are harsh. Getting a Taxi or Uber to the dock is a great way to avoid seriously ruining your vacation!

Also, some of the Cruises actually include or offer Pick-up, we will be sure to point these out.

Where do the Cruises Go?

Sunset Cruise Lanai

Most of these cruises do have a destination point but it is usually just a quiet remote bay. It may be Kapalua Bay or Honolua Bay, but essentially they are just heading for a quiet mooring point to allow you to enjoy dinner.

Not all of the cruises do stop and the larger boats simply find calmer water and drop the Knots to help smooth out dinner service. Regardless of this most of the routes will take you along the Stunning West Maui Coastline. This is the most scenic part of the Island with the deeply eroded valleys and mountains really becoming Visible once you take to the water.

The start point will largely determine which part of the Coast you will sail along, but all of it is stunning and at sunset the colors and low sun really make the mountains pop. In addition to the West Maui Mountains, there will be the Islands of Lanai and Molokai off on the opposite horizon. depending on your location the sun should dip into the ocean around the Island of Lanai, it will certainly be on that side of the boat and not behind Maui. This gives the maximum effect of the sunset and the sky will likely pop into an array of colors from yellow, oranges, and reds to iridescent pinks and purples and finally deep steely blues, there is even the chance of the green flash!

It’s one of the most beautiful sunsets in the world and aboard a cruise such as this is the perfect place to witness it.

If you are looking to head to a particular location you might prefer a snorkel cruise and if you are looking for a Molokini Trip then look here

Will We See Marine Life?

This question has two answers, basically depending on when you visit. If you are coming during Whale Season then there is a really good chance you will see Humpback whales. Especially during the peak season there are just so many whales in this area it’s really very unlikely one will not pop up at some point. The boats do not actively hunt them out, but you really do not need to, and they will slow down and take in any sightings that do occur.

Outside of whale season then things are less guaranteed. There is always a chance of dolphins. They are very prevalent in the areas where the cruises sail, but actual signings are more hit or miss. You may well see turtles, that are cruising on the surface taking a rest, these are pretty common. And there is a good chance of flying fish, launching themselves from the water.

Monk seals are super rare and very well camouflaged on the shoreline but there is always a chance of a sighting.

There are never any guarantees, but the chances are good. But remember these are not Whale Watching tours and wildlife sightings are not a priority for the crew, but they do realize how much we all love them and do what they can.

While these cruises are good for the odd sighing, If Whales are the most important factor, we would look into Whale Watching Cruises instead…or as well!

Best Maui Sunset Dinner Cruises

Ok, let’s take a look at the various cruise operators.

1- Sail Trilogy – Captains Sunset Sail

Trilogy sunset Dinner Cruise
  • Location: MaalaeaLahaina
  • Duration: 2.5 Hours
  • Cost: $162
  • Inclusions: Open Bar, 4 Course Dinner, Tables set for two

Sail Trilogy is a really nice option that offers most of the points that we think make a cruise really worthwhile. They operate from their fleet of Sailing Catamarans which are smaller and more intermate than the larger vessels. The tables are set up for 2 persons so you get your own space which is much more romantic, and the company really does not pack too many aboard the vessel. 22-26 seems to be the maximum number depending upon which vessel is used (55ft-65ft)

This all makes for a really nice experience with very little overcrowding. While you have your own table, you can still get u and move around to get the best view.

Food wise the meal is really good. The offering is a 4-course menu which is fixed apart from the Entree. It kicks off with an Appetizer platter, which can change, but our example was Breadsticks with Butter, Smoked Salmon Pitta, Cucumber Cup, and Teriyaki Beef Crustini. This is followed by a Caesar Salad with Blue Cheese Dressing.

The Entree s a choice of Steak, Chicken, Fish, or Veggie. These are all really good restaurant quality but lack a little finesse as they are hauled out to sea rather than cooked fresh on the boat. But this is standard practice. It is disappointing that the Appetizers have no Veg/Vegan Option, although the breadsticks and Cucumber Cup would count as Vegetarian.

Dessert is a selection of three mini desserts and all are pretty good.

The Drink Selection is excellent with a premium open bar and some really epic cocktails. These are served in plastic table wear, which is not perfect, but better than the plastic party cups used by most, and at least they look good in your Photos! I do wish we could be trusted with glasses! There are some great wines on offer and Kona Brewing co provides the beers.

Sailing from both Lahaina and Maalaea we really like Trilogy. They tend to motor quite a lot rather than sail, but it’s still a super relaxed yet still sophisticated cruise along the stunning Maui Coastline.

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2 – Pride of Maui – Luau Sunset Dinner Cruise

Pride Of Maui
  • Location: Maalaea
  • Duration: 2 Hours
  • Cost: $175
  • Inclusions: Open Bar, Buffet Dinner, Polynesian Show

This is a great option for those with limited time or limited Budgets. This cruise is a combination of two really popular activities in Maui. A Luau and a cruise all in one, and in the right season you are probably going to get a little whale spotting as well!

The Luau is not the best on the Island, and you can definitely do better, but it’s around the same price as most Luau’s, a lot cheaper than the South Maui offerings, and you are getting a Sunset Dinner Cruise rolled in as well. It is also a pretty good cruise too. The Pride of Maui is a really nice vessel. It is a large powered catamaran that is very stable and well-equipped.

They do allow quite a few guests on, almost 60, but the space is large and the vessel could handle a lot more so it never feels too crowded.

The Dinner is of course Buffet Style as it is a Luau Feast and features a good selection of dishes. Artisan Cheese and Crakers act as the appetizer and then there is a large selection of Buffet Favorites. Baby Back Ribs, Shoyu Chicken, Roasted Coconut Sweet Potatoes, and Stirfry Veg. Dessert is a selection of tropical Hawaiian Favorites and you can always head back to the Cheeseboard if that’s your thing.

Their Open bar is good, with a Wide Range of beers, from Maui Brewing Co. The wines are on the cheaper end and cocktails are all pre-mixed and served in plastic cups, but they flow really freely.

The show is super basic, as space would dictate, with only a few dancers doing some pretty basic moves, but you can’t really expect a full-on stage show with such limited room. This does make the show really intimate with loads of crowd participation.

We would always recommend doing a Luau AND and a cruise, but if your budget or time just does not run to that then this is a great option. It’s even a fairly decent option when taken as a stand-alone cruise it ticks most of our boxes and you will certainly have a great time. However taken as a standalone Luau, it’s probably the worst on the Island, but really it’s a cruise first, Luau Second.

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3 – Alii Nui Royal Feast Cruise

Alii Nui
  • Location: Maalaea
  • Duration: 2.5 Hours
  • Cost: $279
  • Inclusions: 3 Course Gourmet Buffet Menu, Premium Open Bar, Transportation Included

Alii Nui offers probably the finest Dinner Cruise available on Maui. The luxury 65′ yacht is one of the finest on the island and runs at 40% capacity so is never crowded, the food and drink are exquisite, the service second to none, and the overall experience one of the best, with everything taken care of. But then it should be, as this is easily the highest-priced choice out of our picks.

One of the big perks is the included Transportation which is a nice touch, taking the worry out of getting there and getting back after hitting the open bar. This helps offset the cost slightly, but then an Uber from most resort locations is only $25-35 so it does not offset things enough to stop it being the most expensive option.

The Buffet is the best Buffett offering on any of these cruises and is packed with delicious high-end choices. Prime Rib, Seared Ahi, Babyback Ribs, Pesto Chicken, and various Meat Free options. Desser is chocolate Tuxedo Cake, Cheesecake Chocolate Covered Strawberries, and a Sweet Raspberry dessert wine! It’s an epic feast.

Drinks are all top shelf with a fantastic Wine Selection, great spirits, and local beers. The crew are excellent and really goes the extra mile.

It really is a great cruise but that price puts it out of our range really. We feel this is largely catering to those staying in the ultra-high-end resorts of Wailea and will arrange the trip via the Hotel Concierge and probably never ask how much it costs!

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4 – Maui Princess

Maui Princess
  • Location: Lahaina
  • Duration: 2.5 Hours
  • Cost: $159
  • Inclusions: 2 Drinks, 3 Course Dinner, Large Open Air Deck, Maui’s Largest Vessel

It’s funny as we always think of Lahaina Harbor as the smaller port that deals with the smaller vessels and on the whole, this is the case, however, the largest vessel, The Maui Princess actually sails from Lahaina, not Maalaea. The 120 ft Maui Princess is a large luxury ocean yacht that really is a joy to sail on. While the modern Sailing cats are great they have a really bland fee about them but the Maui Princess is dripping in Character.

The Ship can hold 149 passengers but it allows a fraction of that and ensure everyone is seated outdoors on the top deck, this cannot be said for all the vessels that operate Dinner Cruises. Tables are set for 4 which can be a little cramped if you are seated with strangers, but you can normally find a table alone as long as it’s not too busy.

The meal is very good and is served direct to your table. A garden Salad started things off followed by an entree of Prime Rib, Roasted Chicken, Macadamia Nut Crusted Mahi Mahi Fillet, or a Vegetarian Option. There is only one dessert option but that is a very tasty Cheesecake.

Drinks are more of a letdown. You get a welcome Mai-Tai and then one other drink. There is a cash bar so there is no need to go without and prices are pretty reasonable considering the captive audience. But we really don’t like this way of doing things when there are Open Bars available for similar prices.

Overall the star of this cruise is the Maui Princess, it’s a really beautiful vessel and a real treat to sail on. Sure we are not fans of the Drinks policy, but not everyone is as big a drinker as we are!

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5 – Sea Maui – Premium Dinner Cruise

Sea Maui Cruise
  • Location: Kaanapali
  • Duration: 2.5 Hours
  • Cost: $122
  • Inclusions: Open Bar, 3 Course Dinner, Beach Entry

This comes in at the budget end of the spectrum but offers pretty much everything the other tours offer just a little lower end. The Vessels are one of Sea Maui’s Great Sailing Cats that offer a really fun and relaxed sailing experience. They may or may not be under real wind power depending on conditions but it’s still a very pleasant journey regardless.

The big issue with this tour is both a blessing and a curse. The Cruise Sails from Kaanapali Beach. This is super convenient for the folks staying in the many resorts lining the beach. It’s great to walk direct from the hotel to your cruise and then back afterward, with no worries about indulging in the open bar. The downside is you will be required to board via the beach loading steps. This is not always particularly dignified and will result in wey and sandy feet. Anything long worn on your legs could also end up soggy, and in heavier surf even shorts!

For some, this is all part of the charm. But it suits their excellent Cocktail cruise more than the Premium Dinner Cruise. Most people want to get dressed up for dinner and this option doe snot really allows that as well as others. Still, the chance to hit that bar hard is mighty tempting!

Food is fairly average, but tasty and plentiful. starting with a Ceasars Salad, and then it’s a hearty Buffet of Chicken, Slow Braised Shortribs, Fresh Fish, and various sides. The Open bar is cheap and cheerful. There is a good offering of beer, wine, spirits, and basic cocktails. But most importantly it’s very free-flowing. Empty Glasses are a no-no!

overall it’s a great fun option for those staying at Kaanapali. The convenience really adds to the value (No Uber/Taxi, Parking Fees, designated Drivers, etc..) If you are coming from elsewhere they will validate for free parking at the Whalers Village Carpark, but overall we think this is best suited to those already at Kaanapali

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Other Options

There are several other options out there but on the whole, our top picks are the cruises above, the rest all seem to have significant pitfalls that might mean a less-than-perfect trip. Overall we are not in the business of badmouthing companies, but for one reason or another, we are not as fond of the following tours as we are the top 5 above!


Pacific Whale Foundation

  • Location: Lahaina
  • Duration: 2 Hours
  • Cost: $165
  • Inclusions: Open Bar, 4 Course Dinner, Certified Marine Naturalists on board

This is the best of the rest. It’s a good tour and especially worthwhile in Whale Season, as the onboard naturalist is a great asset for pointing out any whales along the way. The meal is pretty good with an Artichoke Dip to begin, A Salad Course than an onboard grilled Entree. A Triple Chocolate Brownie is a dessert.

The vessels are large and modern and you are guaranteed outdoor seating, but they can be really crowded and there is a 3-drink limit as opposed to an Open Bar.

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Quicksilver

  • Location: Lahaina
  • Duration: 3 Hours
  • Cost: $144
  • Inclusions: 2 Drinks, 3 Course Dinner, Live Music

The Quicksilver cruise is an ok option but overall the vessel feels more suited to Snorkelling. The meal is served indoors which is a bit of a letdown but there is loads of space outside afterward. It’s a pretty decent meal and is served at your table rather than a buffet. There are also only two drinks included.

The is always live music which is a nice touch

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Calypso

  • Location: Maalaea
  • Duration: 2 Hours
  • Cost: $144
  • Inclusions: 2 Drinks, 3 Course Dinner, Triple Decker Boat

The Calypso is an absolute monster of a Vessel. It really is something to behold seeing it up close, but while impressive, it’s not really the sort of Vessel we enjoy seeing in Maui’s Waters. It’s a juggernaut of a tour ship.

The offering is ok, with a decent meal but only two drinks. This sort of gawkish monster is just not really for us.

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Hula Girl

  • Location: Maalaea – Lahaina – Kaanapali
  • Duration: 3.5 Hours
  • Cost: $110
  • Inclusions: Cash Bar, Ala-Carte Menu, Restaurant Style Dining

This is totally different concept from all other cruises. On the face of it, it seems a real bargain, but there is very little included. Instead, the CAtermatran operates as a floating restaurant. You get a nice cruise down the Wes Maui Coastline, where the vessel will find a nice place to moor up. Then you choose your meal from the ala-carte Menu and pay for what you eat. Drinks-wise it’s the same deal. Nothing is included but you can order what you like from the cash bar.

Admittedly the food is top-notch, this is all restaurant quality and everything is cooked onboard. The drinks are great and not too price, but a couple of drinks, an appetizer, and an entree are going to run between $70-100 and that’s on top of the $110 boarding fee.

We get operating as a restaurant but dislike the need to pay $110 to enter it! Still, the food is very good. But we are always going to plump for an all-inclusive package. Especially with an Open Bar!

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Holiday Cruises

Most cruise companies offer special holiday cruises that can have added attractions or just celebrate special days. Halloween Cruises, Fourth of July Fireworks Cruises, and Valentine’s day romantic Cruises. These are all worth looking out for.

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FAQ, Tips, and Advice

Get there Early

Most of the time these cruises are first come first serve and as such the early bird catches the worm. This is one reason we love Lahaina, as we can get into town early grab a happy hour drink and then head out on the cruise.

A great seat can make the world of difference on busy cruises so it pays to be early and get aboard to snag those precious rail seats!

What to Wear?

As you arrive at the dock it is likely to be 82-86°f (28-30°c) and the thought of anything other than light clothing seems ridiculous. However, it is incredible how much cooler it can feel just offshore. The water retains non of the heat the land does and the ocean breeze can really drop these temps right down. Especially as night approaches it can be really quite cold aboard an open-air boat.

While it can feel really frigid it’s actually only a few degrees cooler so a simply light jacket or cardigan is all that is needed to fight off the “arctic blasts” but they really can be essential once the sun has dropped or if a little cloud cover moves over.

This is also West Maui, and rain showers can and DO roll in. They are usually short-lived but very inconvenient for a cruise. All boats will have an undercover area for this very purpose.

Weather Cancellations

The Hawaiian Island are slap bang in the middle of nowhere, surrounded by thousands of miles of empty ocean, filled with fierce storms and raging winds. Large swells can and do hit the Islands frequently, even if the skies are clear and the wind light. While The tourist side of Maui is well protected from these by the outer islands of Lanai and Molokai, from time to time the swells are right and the surf is huge. You do not want to be aboard a touring boat in these conditions.

Nor if visibility is poor and rain persistent, you will have no fun at all. So in these conditions, the captains will call a No-Go for the weather. Trust us, if they do, you don’t want to be out there. The captains would sail in far worse conditions than you would tolerate, so if they say no, they mean it.

It’s super disappointing but these things happen. There are usually two options. One, re-arrange for another night if there is availability, or two receive a refund. No one wants a refund for a trip they have looked forward to but if you can’t make a revised time work between you and the company then there is little other option.

Remember though it is THEY that have canceled on you, so they must provide a refund.

One Hand For You, One for the Boat!

The crew will remind you of this rule, but it’s a well-worn ocean safety tip. When moving around the boat, always have one hand for you and one for the boat. Essentially, hold onto something at all times. This will stop those awkward and potentially painful and damaging little spills that can occur when the boat hits an unexpected wave.

Sea Sickness

The combination of wide, stable boars and short trip duration means Sea-Sickness is not a huge problem on these trips. There needs to be more rocking and for a longer duration to affect most people. Really sensitive folks may work up a bit of a tummy, but they should be well-versed in the various over-the-counter remedies available.

Of course, it could be your first foray into cruising and you may not be aware you are sensitive. In that case, the best course of action is to stay near the rail and shoot for distance! Focus on the horizon as this helps lessen symptoms.

Whatever you do, DO NOT head indoors. This does not help at all. And the absolute worst place to be…The Toilets…speaking of which!

Will there be Toilets?

All of these tours come equipped with either restrooms or what is known as a Marine Head. It’s not a toilet, but it is somewhere you can go to do the things you would in a toilet. They are just far more sensitive to solids and can clog easily. But really that is more of a Crew problem than a You problem…

Can I bring a Camera or take photos?

Absolutely. Pics and Videos are positively encouraged, especially if you are going to splash them all over your Socials as that’s basically free advertising! The crew will happily help you take group photos or ask another friendly guest, often people will swap so you both get your group or couple photos.

One word of warning Ariel has a huge collection of Mobile Phones now, all from hapless tourists who forgot how slippery their Phones can be when on a rocking boat, out at sea. A dropped phone is very easily lost over the sides as there is often no lip!

Are these Rowdy Booze Cruises?

Not at all, the drinks might be flowing but these are anything but Booze Cruises. Some of the Cocktail Cruises are a bit more drinky, but even then, they are nowhere to the drunken debauchery that the term booze cruise conjures up, you just won’t find that in Maui.

Will we see Wildlife, Whales, and Dolphins?

We already answered this, but in case you missed it see here, and in short…Maybe.

Have Your Say

Have you been on a Sunset Dinner Cruise in Maui? Who did you sail with and what did you make of the Experience, the Dinner, and the Drinks? We would love to hear your experiences and thoughts. We have tried to answer your questions but if you have any other pressing queries then fire away in the comments below and we will do our best to answer.

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