Best Maui Sunset Cocktail Cruise? – Find Your Dream Maui Cocktail Cruise

Imagine gently cruising along the stunning Pali coastline of Maui, the ocean breeze gently cooling your face as you sip a fancy cocktail from a tall glass, the sun gentle sinking into the perfect blue Pacific Ocean as Whales breach in the distance and Dolphins play in the bow wave of your sailing yacht. It sounds like the absolute perfect evening, and if you believe the glossy promotional material of the cruise providers it is exactly what could await you on your Maui Sunset Cocktail cruise.

The reality, unfortunately, is not quite so perfect and romantic as the imagery, but, honestly, it can be not that far off, IF you choose the right cruise. This is where our guide to the Best Maui Sunset Cocktail Cruises comes in. We take you through the best, and worst, cruises available on Maui and show you where you can get the absolute best experience, what to expect on the cruise and what the various Cruise companies offer.

Maui Sunset Cocktail Cruise

We start off by explaining a few details about these types of cruises before digging into the actual cruises on offer and which of these we prefer.

Cocktail VS Dinner Cruise?

First of all, let’s just explain the difference here. Cocktail cruises are short relaxing sails along the coastline. They offer an Open Bar with a selection of cocktails, Beers, and wines, along with a selection of Pupus, or appetizers. Dinner Cruises are longer and more complete packages offering a sit-down 3-course meal, drinks, and often live entertainment, they are naturally more expensive too.

This article is focused on the Cocktail Crusie side of things, but we have a full article on Dinner Cruises here, Picking the right Dinner Cruise is even more vital as there are quite a few more variables.

We really like the cocktail cruises as they are just a little more relaxed and offer more time to just relax and enjoy the setting sun. These tours tend to be on the smaller catamaran-style boats so are far more intermate than being crammed onto the huge super yachts used on some of the Dinner Cruises.

Finally don’t think that because all that is on offer is Pupus that you will still be hungry or will need to eat later. These are usually large portions and all you can eat in most cases, or at least were before Covid. In any case, they are large portions that most people would consider a meal, it’s just they are served in a more casual manner.

Sunset Cocktail Cruise Experience

West Maui Mountains

These cruises are some of the shortest ocean excursions offered by cruise companies. They simply offer a nice sail at the best tie of the day, while enjoying some drinks and nibbles along one of the best coastlines in the world.

Check-in is usually 15-30 mins before departing but on the whole, we try and get there even a bit earlier, as boarding first gets you the pick of the seating. Some of the cruises offer open seating while others provide tables. The prime positions are always the nets at the front. If you can snag a spot on the nets which are strung between the twin bows of the Cat, you literally have the Ocean beneath you, and unobstructed views out to the bow.

Where ever you are seated you are always free to move around, take pictures and enjoy the stunning scenery. These Cruises primarily operate along the west coast of Maui and stick to the calm coastal waters of the Channel. The Scenery here is truly stunning, with the beautiful west coast mountains off one side and the islands of Molokai, and Lanai off to the other.

The West Maui Mountains are beautiful from most places on Maui but they really come alive from the water the high peaks and deep valleys are just more visible from offshore as you increase the line of sight it really changes the perspective.

The vessels tend to be on go slow on these cruises and in no hurry to get anywhere. As soon as you are out of the harbor the drinks services will start. The drinks tend to flow pretty well and most people will have time for at least 3-4 drinks during the sail. You can probably manage more if you are very eager, and the open bar cruises will keep the drink flowing, but as you are at sea, there will be limits, and how drunk can someone get in 2 hours? Most cruises operate a Bar, but some will have table service.

Around 30-40mins in the Pupus Apatiser will be served, these usually are served from a buffet but some boats, especially post covid, will serve the appetizers individually, as a platter. Most cruises are pretty generous and most people will not need to eat again after the cruise. We do not make dinner plans for after the cruise as the food served is usually enough.

After this, it’s just time to enjoy the sail, look out for wildlife and wait for the main event. Drinks will continue to be served right up till the end with the last orders being announced so you can get your last drink before heading to the harbor (or beach)

The Cruises leave fairly early and the sunset will arrive pretty late on in the cruise as the crews like to be heading into the harbor before dark. The start times will be adjusted for the time of year to ensure you get the best view.

Depending on the time of year, and where you are sailing from, the sun dips into the ocean behind or to the side of Lanai but it will be on the left-hand side of the boat as you sail north, or vice versa. So try and get a seat on that side of the boat, remembering you will be getting the sunset on the way out, so you will want to be mountainside out and Island/Ocean Side on the way back. If you are not sure just ask the crew (but do it discretely so others don’t overhear and beat you to the best spots!). If you do not manage this, don’t worry, people will be moving around to get a view regardless.

Some Cruises feature live music, but if not there is usually a nice selection of island rhythms played over the speakers to help the mood and up the Aloha.

Sunset Cruise Lanai

Where do the Sunset Cocktail Cruises Sail from?

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

Maalaea Harbor

This is the main harbor on the tourist side of the Island and handles most of the larger tour boats. These boats tend not to offer Cocktail Cruises but instead host Dinner Cruise options. There are still a few smaller Cats that Operate out of Maalaea though. If you are in South Maui this is one of the few options, but it’s not too far for many people in West Maui either.

There is plentiful parking at the Ocean Center, but be warned, these Cruises offer Open Bars, and Drink Driving is never a good idea! A very fast way to REALLY ruin your Vacation.

Lahaina Harbor

Lahaina is the second location these cruises sail from. Located pretty centrally on West Maui this is the best option for those Staying in the area. Anyone staying in the South would need to drive right by Maalaea to get here, and vice versa for most people staying in the West. Again this is a well-established harbor but on a much smaller scale than Maalaea. You still board the boats from the dock and in sheltered waters.

Kaanapali Beach

The final spot these tours depart from is Kaanapali. Those in the know will realize there is no port or harbor at Kaanapali so how do you board a boat? Well, it’s not always as simple as at the two harbors! If conditions are calm, then the Crew will literally beach the vessel and allow guests to board via the steep boarding steps. If the conditions are rougher or the vessel does not have such an option you may be asked to ride a small tender out to the Boat.

It’s not always graceful and anyone with mobility issues may struggle. We love the ability to be able to board the vessel right from the beach, but this option is not for everyone. You will get sandy and wet feet and long flowing dresses may end up a little soggy. If you want the easiest boarding head to either harbor.

Which is best? this really depends on where you are staying. For anyone in South Maui Maalaea is the best option, for West Maui then Lahaina is a great option, but those staying in the many resorts along the Kaanapali Beachfront will really appreciate the ability to walk to the Boarding point.

Where do the Cruises Go?

These tend to be cruises that do not have a destination. The route will depend a little on where you launch from and also on the weather. Essentially as there is no snorkeling element to these cruises there is no real need to go anywhere so they will head for the best ocean conditions. Here you are looking for the sunset and the stunning views of the Pali Coast, so anywhere along the West Maui Coastline will offer this in Spades.

So if you sail from Lahaina or Kaanapali you can travel either direction, but the conditions are usually worse the further you head north so these cruises usually head south toward Maalaea. But sometimes you can head a little in both directions. Whereas Cruises from Maalaea will usually head north up along the West Maui Coastline.

If you are looking for a Cruise that goes somewhere, like Molokini or Turtle Town, and actually allows you to get in the water and Snorkel then you will need to do a daytime cruise there are a lot available and we have guides to these here:

Will We See Marine Life?

Molokini Snorkeling Humpback Whales

There are never any guarantees and the purpose of these tours is not whale-watching or wildlife spotting, but Maui’s waters are teaming with life, and the crews no how much the guests love seeing wildlife so will do their best. In Whale Season Nov-Mar, you are very likely to see Whales. There really are everywhere, especially in the waters of the West Maui Coast.

Dolphins are less reliable but possible at any time of the year and there are often turtle sightings. Really if seeing marine life is important to you, then these are not the best tours, but there is always a good possibility of seeing something, especially during Whale Season.

Some Boats also drop a few lines off the back to see if they can pick up any sport fish as you cruise along. This is mainly speculative, and we have never seen anything caught, but the crews always assure us they do from time to time. We have to believe them as they probably wouldn’t bother otherwise!

If seeing Whales is really important to you then we recommend looking into the various Whale Watching Tours available.

Best Maui Sunset Cocktail Cruises

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

Sail Trilogy

Trilogy sunset Cocktail Cruise

Sail Trilogy is a large operator and offers tours on one of its 6 Trilogy Catamarans. They offer regular Sunset Cruises from all three locations. Trilogy aims to be a high-end luxury option as opposed to a booze cruise. The tables are nicely spaced out and there are plenty of other seating options around the boat where you can escape. The trips take a maximum of 26/22 people depending on the vessel so there it’s lots of space.

The Catamaran is a Sailing vessel but they are under diesel power most of the time, but they do try their best to get under wind power.

The food is some of the best available, but despite this and it being called Gourmet don’t get your hopes up to high or expect too much. The food is still mass catering so it’s not going to be Michelin-star quality, but it’s pretty tasty. You get some Kalua Pork Sliders, Chicken Skewers, Tomato and Mozzarella Skewer, and Hummus with Carrot and Cumber. along with a tasty dessert. It’s a good portion and most people will not need dinner as well.

Drinks are excellent using premium liquors for the cocktails that are served in glasses, albeit plastic, rather than plastic cups like most cruises offer. There are a good selection of craft beers such as Kona Brewing Co’ and some good wines including Prosecco! Drinks flow really well and you won’t be waiting for top-ups long. The Cocktails are all made with real ingredients and not pre-mix and are really good. The Margaritas are great as are the Old Fashioneds. However, we are just too much of a Mai Tai snob to accept Coconut rum in one!

Overall it’s a great experience wherever you sail from. The low numbers, good food, and great service make this one of the best trips on the Island and about as close as you are going to get to that perfect Hawaiian Sunset cruise.

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Sea Maui

Sea Maui Cruise

  • Location: Kaanapali
  • Duration: 2 Hours
  • Cost: $85
  • Inclusions: Open Bar, Beach Pick-Up, Pupus, Live Music (Tue & Thu)

Sea Maui offers a really fun party boat kind of cruise. The drinks flow and the mood is lively. There is live Music on select nights but expect a fun Island vibe every night. While we say it’s a bit of a party boat, it’s still very mellow compared to the rowdy party boats found in some parts of the world, so do not expect a booze-fueled rampage, just a light mellow vibe with some upbeat island music, flowing drinks and a beautiful sunset. It’s just a bit more of a party than some of the more romantically based cruises.

It certainly comes in at a really enticing price point and is one of the cheapest options on the list. But it doesn’t really forfeit anything to achieve this. They do on occasion cram up to 48 people onto the fairly small 55ft Catamaran, which can feel pretty packed. But with the vibe being party boat over a romantic cruise, then this can work out ok, but getting a good spot can be challenging when it’s busy. They will sail with only 10 people on board however so you can get really lucky!

Food is decent and plentiful, but far from Gourmet. Chicken wings, Shrimp Skewers, some Veggies, and a pretty tasty Sundried Tomato Foccacia. It’s a hearty feed, but not one to write home about, but this is to be expected at this price point. Drinks are again pretty basic, some ok cocktails made with cheaper fruit juices and served in plastic cups, and local beer, wine and fizz, and a selection of spirits. The key is that they flow pretty well with good pours and no limit on amounts.

Overall it’s a more basic option than some but it comes at a really hot pricepoint and for those staying at Kaanapali, it’s really great to walk out of the hotel, onto the beach, board the Cat, head off for a stunning sail, enjoy some good drinks as the sun sets and then stumble off back to your hotel. The offering is definitely more budget, but one part that isn’t is the mindblowing Sunset and West Maui Scenery. This is basically priceless and you get the same no matter what cruise you choose!

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Pacific Whale Foundation Ocean Spirit

Pacific Whale Ocean Spirit
  • Location: Lahaina
  • Duration: 2 Hours
  • Cost: $133
  • Inclusions: 3 drinks, Gourmet Pupus, Trained Naturalist onboard

The Pacific Whale Foundation is the biggest Boat Tour operator in Maui and has a large fleet of vessels that take tourists out primarily to do Whale Watching Tours. While there is a bit of debate around the Foundation, as they give the impression they are a charity, really this is just one big commercial operation and as long as you treat them like this there is no issue really. The Foundation does do some good work with Whale conservation and other marine live work, which is not to be ignored but the main Tour Operating arm is a Commercial enterprise.

On to the Sunset Cruise. This is one of the more expensive options but also has some of the best food. Ahi Tuna Crustini, Kalua Pork quesadillas , Tiger Prawn Coctail, Tortila Chips and Cheese and Fruit platters. Finished off with Chocolate Kula strawberries!

Drinks are a little disappointing as it’s not really a Cocktail cruise, but the bar is stocked with beers, wines, and Spirits, but you are limited to 3 Alcoholic drinks, which isn’t too bad in 2 hours but we prefer the freer flowing drinks of the open bars.

There are two options here, the Family Cruises (Sunday – Thursday) and the Adult Only Cruises (Friday and Saturday). There really isn’t much difference here apart from the fact Kids are not allowed o the Adult cruise, so if you want a kid-free cruise it’s an option.

The Pacific Whale Foundation has some pretty big boats in their fleet, but the Cocktail Cruises are run on the more compact, Ocean Spirit luxury sailing catamaran. This is a very similar vessel to the option above.

This is a really good choice in the Winter Months when the whales are around as they go the extra mile to find you some whales before the sun sets. There is a Trained naturalist on every cruise who will help the crew hunt out the whales and tell you all a lot about them.

Out of season you still get the naturalist who will still do their best to find you some marine life such as dolphins, flying fish, and Turtles, but things are a little less abundant out of Whale Season. You are going to have a great cruise along the most beautiful coastline, but wildlife sightings are less common.

We think the Pacific Whale Foundation Cruise is a great option in the whale season as the extra knowledge and desire to find the whales are pretty impressive. But the reality is, all the cruises are pretty good at finding whales as they are so abundant, but you do get that extra narration here. Out of season, the extra cost makes the other options a bit more appealing, but the food is excellent aboard Ocean Mist!

There is another option too out of Maalaea if you can’t get to Lahaina, it’s only on select nights but is actually a little bit cheaper.

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Sail Maui

Sail Maui Sunset Cruise
  • Location: Lahaina
  • Duration: 2.5 Hours
  • Cost: $95
  • Inclusions: Sailing Cat, Open Bar, Pupus

Sail Maui is one of the few cruises that use proper performance sailing catamarans, It’s a nice feeling actually sailing rather than motoring along under diesel power, it’s not guaranteed, but if the winds blow they put up the sails.

They offer a light Pupus menu which is pretty basic but certainly substantial and uses fresh ingredients. The drinks menu is mainly craft beers and wines but they offer basic cocktails too such as Mai Tai’s

Overall this is a really nice option due to the fact they actually get the sails up and glide along rather than firing up the engines. This does mean the vessel is s touch slower, but then this is one of the longest cruises on the list.

The crews are friendly and all know their stuff as they are actually operating the Sailing Catamaran as it’s meant to be used. Numbers are also kept pretty low so you always have space and somewhere to relax and take in the stunning scenery and sunset.

For return visitors, this company used to be called Paragon Sailing, but they rebranded when they bought a second 65′ yacht, ALIHILANI to go with Paragon, and they offer tours on both vessels.

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Scotch Mist

Scotch Mist
  • Location: Maalaea – Lahaina – Kaanapali
  • Duration: 2 Hours
  • Cost: $90
  • Inclusions: Real Sailing, Champagne, Chocolates

This is the only tour that does not offer food, but there are plenty of dining options once you get to Lahaina so don’t worry too much. Drinks are limited to Fizz, White Wine, or Local beers and these are unlimited, but this is not a Booze cruise and service is a little slower.

Overall it doesn’t seem like this one has much going for it, but the real highlight here is the fact you will be in a really small group, 22 max on a real Sailing Yacht using wind power to cruise the ocean. All other options use sailing cats and most spend most of the time under Diesel power. But the Scotch mist is just totally another world.

This is pretty high adrenaline activity at times, when the seas are calm the yacht performs some pretty tight banks and turns which are a real thrill and when the ocean is a bit more choppy it really gets exciting as the vessel crashes through the waves.

It’s not as comfy or stable as the Cats, but this is the whole point. If you want a more authentic sailing experience the Scotch Mist is unbeatable.

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Hula Girl

  • Location: Kaanapali
  • Duration: 2 Hours
  • Cost: $98
  • Inclusions: Nothing

Hula Girl is another tour that sails from Kaanapali Beach and offers a different experience from most of the other tours we mentioned. The Food and Drinks on the Hula Girl are better than on any other boat we have mentioned. But this comes at a cost…literally.

The Hula Girl operates as a floating restaurant, so all items are purchased ala carte. For example, a Sharing Platter is $21.40 for two, a Hula Hawaiian Sandwich is $15.95, a Mai Tai is $12, and local beer is $6.

When you consider that most other boats have appetizers included along with an open bar, suddenly this seems a very costly exercise.

We accept that the food is restaurant quality, but we don’t usually have to pay nearly $100 to get into a restaurant. For us, this option makes no sense. If we want to upgrade our food we would look at the many Dinner Cruise Options. And we just naturally gravitate towards an open bar by nature. Yes, the cocktails are excellent, but we prefer them flowing.

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FAQ, Tips, and Advice

Get there Early

Some seats on these cruises are better than others and on the whole, it’s first come first served.

What to Wear?

When you board the chances are you will be HOT. I can still be scorching on shore at the tie the cruises depart. However once out to see it can turn chilly quite quickly and but the time the sun sets, especially if there is a breeze it can be decidedly cold!

So the key is to make sure you have a jacket or cardigan you can pull on if the nip in the air just gets too much. A lot of people get caught out by this, it really can be deceptively cold once on the water and it’s the large temperature differential that makes you feel the cold.

Also, Remember most boats operate a shoes-off policy, as this is customary in Hawaii, so don’t worry too much about your footwear!

One Hand For You, One for the Boat!

The crew will definitely remind you of this during their mandatory safety briefing but just so you are forewarned. When moving about the boat, the rule is one hand for you one for the boat. This means holding on to something at all times. There are railings all around the boat and always something to grab. It’s amazing how easy it is to get knocked off balance by an abrupt wave or unexpected movement. This is especially true when carrying drinks!

Sea Sickness

These are fairly short cruises, and the Cats are pretty stable platforms so sea sickness is not often a big issue for all but the most sensitive. Apart from medication or sea sickness bands, there is not much you can do, other than the standard Hawaiian Practice of holding the rail and shooting for distance!

The main trick is to stay on deck and look out to the horizon and whatever you do, don’t head for the Lavatory!

Will there be Toilets?

Well, there will be a Marine Head, which is what nautical types call a Toilet. Two hours is not long to go without the loo, but with the drinks flowing you will probably need one, and besides these boats are designed for longer trips too.

Can I bring a Camera or take photos?

Of course, Photos are positively encouraged, especially if you are going to Instagram them and provide free advertising!

The thing to consider though is the possibility of losing your device. This is especially true of phones. Cameras tend to have Lanyards, but phones can be slippery devils, and when if the boat is bouncing around in the swell, they are easy to drop. A lot of the deck has no lip and a phone can easily slip into the water…if so you won’t be seeing it again, that belongs to Ariel now!

Are these Rowdy Booze Cruises?

Not at all. Some call themselves Booze Cruises, some Happy Hour Cruises, but the term Booze Cruise conjures up images of loud music, rowdy parties, and alcohol-fueled debauchery! These are NOTHING like that. The term Cocktail Cruise is the perfect terminology, even the most raucous of these, it’s still a case of a relaxed cruise, sipping drinks as the sun dips into the ocean.

Spring Break this AINT! This is of course very subjective as to whether it’s a good or bad thing, we just give you the facts and let you decide!

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 Cruise in Maui? Which cruise did you choose? Which company did you sail with? How did you find the experience? Did you see any wildlife? Let us know your thoughts in the comments below and if you are looking on taking your first cruise let us know your thoughts on our list, and as always any questions just fire away

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