7 Best Maui Sunset Cruises For a Great Night Out

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I’ve traveled all over the world and one of the things I always look forward to doing in every location is watching the sunset (and now that I have young kids I’m usually also watching the sunrise). 

While we’ve seen some great sunsets, none compare to Maui. The sunsets here are unbelievably spectacular. Pink, purple, ombre skies that sometimes you can’t even believe are real. And while you can certainly see these sunsets from land, there’s something very special about enjoying them from the water. 

If you’re looking for a Maui sunset cruise that really wows, we have a list of the best of the best, and what makes each one so special. Living on Maui for three years we were able to experience more than our fair share of these, so we’re happy to be able to share our advice with you!

Want to get right to it without reading all the details? Jump in and book these recommended tours:
1. This is the cruise to book if you want live music
2. Book this for a convenient Wailea departure
3. Getaway from the crowds with this small group sail
4. Luau or cruise? Get both with this sunset luau cruise
5. Enjoy a full dinner cruise with your sunset
6. Use code HVG10 to get 10% off with Sail Maui
Need more time on (and in) the water? Make sure you check out our top snorkeling tours on Maui.

Sunset Live Music Cruise (Ka’anapali)

Head out onto the water with a drink in hand while being serenaded by an on-bard musician. This sunset live music cruise really knows how to have a good time. Offered every Tuesday and Thursday, you and approximately 47 other guests will board a 55’ catamaran for two hours of fun. 

Included is live music, an open bar (beer, wine, champagne, and mixed drinks), and pupus (light appetizers). 

They depart from Ka’anapali beach (how convenient!) and if you’re not staying in Ka’anapali you’ll get a 4 hour Whalers Village parking validation. Note that because of the convenient location and not needing to drive to a harbor, they do beach loading. That means you’ll be wading into the water up to your knees in order to board. Long dresses and pants aren’t ideal here. 

If you’re not interested in live music, or you can’t go on Tuesday or Thursday, they offer a regular sunset cruise (sans live music) all other days of the week. Learn more about their standard Ka’anapali sunset cocktail cruise.

Sunset Luau Cruise (Ma’alaea Harbor)

Can’t decide between going to a luau or enjoying a sunset cruise for an evening activity? Do both with this sunset luau cruise! While this isn’t a true full luau, you’ll still get to experience traditional music and dance with Maui’s gorgeous sunset as a backdrop. 

You’ll board the maxi powered catamaran which leaves from Ma’alaea Harbor in central Maui (paid parking available). On board you’ll be treated to appetizers, a full dinner, and an open bar with beer, wine, and mixed drinks. During the cruise you’ll have the opportunity to enjoy Polynesian dance, which makes this experience part sunset cruise, part luau. 

The boat has a coast guard approved occupancy of 149 people, but they intentionally limit it to 60% of capacity so there’s extra space to stretch out. While this is the most expensive cruise on this list, you do get to see hula and a full dinner.

If you prefer to keep your luau and your sunset sail separate, we have a list of the best luaus on Maui.

Catamaran Sunset Sail

Spend 2.5 hours aboard this 48 passenger, 65’ catamaran, with plenty of room to spread out. Excited for a little more adventure? Head up front to the trampolines (though you might get a bit wet). 

They have two different boat options, both leaving from Lahaina Harbor. The first is on a 65’ Catamaran, with capacity up to 48 passengers. The second cruise on the Paragon is limited to 25 passengers. 

On both, you can enjoy pupus as well as an open bar with cocktails, wine, and beer. 

And if you’re booking with Sail Maui, make sure to use our discount code at checkout (HVG10) for 10% off your cruise. 

Adventure Sunset Sail

Staying in Wailea or Kihei? This is the sunset cruise you want to be on. This Adventure Sunset Sail departs from Maluaka Beach, a very convenient South Maui location. The adventure part of this sunset sail is that you get to enjoy a beach loading, which means you should expect to get wet! We happened to go out on an evening when the south swell was particularly large, so we were in for even more of an adventure! (You can see the video of our experience below). 

Once aboard the 65’ catamaran, you’ll enjoy two hours of sail time, 3 appetizer courses from The Market Maui (a great Wailea deli/restaurant), and an open bar featuring local brand like MauiWine and Ocean Vodka. 

If you haven’t rented a car or you don’t want to drive, they do offer shuttle service from Wailea hotels. But book early as this option tends to fill up! 

We loved this sunset cruise experience and we were able to go out for a great night in Wailea after it ended. Here’s a list of our favorite Wailea restaurants.

Lahaina, Ka’anapali, or Ma’alaea Sunset Sail

Another stellar option is this 2 hour sunset cruise which departs from three different locations on the island: Lahaina Harbor, Ma’alaea Harbor, or Ka’anapali (beach loading). 

A standout feature here is that they offer private tables for two, which makes this a great option for a romantic evening on the sea. They serve plated appetizers and there is a premium open bar with beer, wine, and cocktails. 

If you’ve taken the cruise from Lahaina Harbor, it’s just a short walk to their family owned pizza restaurant, Kapena’s, which we highly recommend!

Champagne Sunset Sail

If you’re looking for a smaller group, this is the sunset sail for you. This is a sailing experience, not just a sunset cruise on their Santa Cruz 50 sailing yacht. With a capacity of only 22 people, this is a fun small group experience. 

While you won’t find as much food on this sail as you will on the others, you’ll enjoy champagne and chocolate. Guests must be 13 years or older to enjoy this experience. 

Premium Sunset Dinner Cruise

If you’re looking for something more than a cocktail and pupu cruise, consider a dinner cruise. Hop aboard this 65’ luxury catamaran for 2.5 hours, relax, and enjoy the spectacular scenery and service. 

You’ll depart from the beach in Ka’anapali — very convenient if you’re staying in Ka’anapali. But if you’re not, don’t worry! They give you a 4 hour parking validation for Whalers Village. Once aboard, you’ll have an open bar and a buffet dinner to enjoy. There’s something for nearly everyone when it comes to the food selection. 

Kids of all ages are welcome. But don’t wear long dresses or pants. This is a beach loading boat, which means you’ll get a bit wet while getting on and off. The convenience of this beach loading cruise can’t be beat. 

Maui Sunset Cruise FAQs

Can you see whales on a Maui sunset cruise?

You sure can! While these aren’t whale watching tours, if they come across a whale during whale season, they will absolutely stop to watch them. Whale season runs December – April, and these sunset cruises all cruise in prime whale watching locations. So the odds of seeing whales during your cruise is pretty good! 

What is the best place to watch the sunset on Maui?

Head to West or South Maui for spectacular sunset views. You’ll get amazing views both from land or from sea. What we love about a sunset cruise is that you not only get to appreciate the sunset over the water, you get to see the island lit up in the glow of the setting sun. 

What do you wear on a Maui sunset cruise?

Pretty much anything you want! Bring a light jacket or sweater, especially during the winter if you tend to get cold in the evening. There is usually a light wind and after a day of fun in the sun, it can feel a little cool. 

If you’re doing one of the beach loading tours, don’t wear long dresses or pants. Expect that your knees and below will get wet. But that’s part of the adventure of beach loading!

How long is a sunset sail on Maui?

Most sunset sails on Maui are two hours, though you will find some that run a bit longer, at 2.5 hours. But they are quick tours that will usually get you back in time for any dinner plans you have that evening.

There’s More to See Than Sunsets

Maui is a dream destination and there is so much to see and do. If you want to make your trip planning easy, our itineraries are here to help. With carefully thought out excursion days, we take you around the island, seeing the best sights, stopping at the best beaches, and eating at the best restaurants. We’ve done the homework for you, now you get to download and enjoy!

My twin sister and I just returned from an amazing birthday in Maui.  I ordered your itinerary for Maui and we relied on it heavily. I just wanted you to know your itinerary was spot on and your recommendations were the best. Thank you so so much.

Kate R.