All Kaanapali Sunset Cruises Reviewed! Pick Your Favorite

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We are big fans of staying in Kaanapali Resorts, West Maui. Snorkeling, sunset sails, swimming with sea turtles, dolphins riding the bow, whale watching tours, we have done it all from Kaanapali. But this is all about sunset cruises! Here are all the Kaanapali sunset cruises in one place, so you can have a Mai Tai and pupu in your hands once you arrive on Maui.

We went out with three of these companies during our visits to Maui, and we plan to go out with more. We are familiar with all the tour companies, having lived on Maui and conducted extensive research.

A visitor to Maui would be hard pressed to find a bad tour operator. Local operators are known for their service and expertise. When comparing these Kaanapali sunset cruises and tour operators, I recommend you look at the following tour details:

• Cocktails with appetizers (pupus) or dinner?
• Dinner buffet or served
• Live music or not?
• How full does the boat feel?

After those big decisions, it will be about the details that we share about the experience, the catamaran sailboat, and the level of luxury.

Note: All Kaanapali sunset cruises are beach loading and are catamaran sailboats. Head to Ma’alaea Harbor for larger boats that depart from a pier for easy access.

While price is a factor in the decision, you’ll find that prices fluctuate fairly depending on the duration and level of luxury. Jump to the yellow box below to make a fast decision on the Kaanapali tour for you. If you’re ironing out the details of your trip, our Kaanapali Guide can answer all your questions!

We love Maui whale-watching! This list of Kaanapali sunsets tours is just that! For more Kaanapali tours, see our Kaanapali Snorkeling Tours and Maui Whale Watching Tours. Better yet, start with our Maui Whale Watching Guide to learn why Maui is the best island for whales.

Jump to the point! Jordan’s favorite Kaanapali Sunset tours by type:
– Best priced luxury catamaran dinner cruise: Sea Maui’s Premium Sunset Dinner Cruise
– Best priced, luxury catamaran cocktail cruise: Sunset Cocktail Cruise
– Best luxury experience in Kaanapali sunset cruise: Trilogy Sunset Cruise
– Best priced dinner sunset sail: Gemini Sunset Dinner Cruise
– Teralani offers more standard options: Sunset Cocktail Cruise and Sunset Dinner Cruise

Kāʻanapali is spelled with an ‘okina (‘) that represents a glottal stop. Think of it as a pause between consonants, like uh-oh. To ease reading, we are omitting the okina in Ka’anapali. 

Quick Tips on Booking a Kaanapali Sunset Cruise

Here is general guidance, based on our experience, for booking a boat tour from Kaanapali.

• Operator cancellation: Though it’s uncommon, a tour company may cancel due to unsafe weather and will notify you via text, email, or a call. You will then have the option to get a refund or to reschedule.
• I recommend booking two to four weeks in advance to get the time and date you want. We have made this mistake! On our last trip over spring break to Maui, we booked 10 days in advance. We couldn’t get the whale watching time that we wanted. Booking four weeks in advance is recommended during the busy summer months of June, July, and August. 
• Concierges can book you a tour when you arrive, but check the price. All the booking links in this article are direct bookings with the local tour operators. No middleman. You are getting the best price. We earn a small commission at no cost to you when you book on our website. We are not partnered with all the tour companies below, as we are sharing all Kaanapali sunset cruises.
• The catamarans offer a complimentary bar (open bar) or drink tickets on their tours. They offer local Hawaii beers, like Maui Brew Co, Mai Tais, and other cocktails. 
• Tipping is not required, but it is welcome! If you had a good time with the crew, you can tip in cash or Venmo at the end of your tour. $10 to $15 per person is customary, but do as much as feels comfortable. Here is our Guide to Tipping in Hawaii.

• Kaanapali sunset cruises are beach loading! Those with mobility issues should consider a tour that departs from Ma’alaea Harbor.
• Until Lahaina Harbor is rebuilt and opened to the public, Kaanapali Beach is the most convenient location for boat tours on the West Side of Maui.
• Storage: There is room on the boat to store personal items. We recommend bringing a beach bag for personal items.
• Bathrooms: All Kaanapali sunset cruises have toilets on board (heads). The catamarans have comfortable toilets but you will need to go down a marine ladder.
• Sea sickness is real, even on luxury catamarans that are more stable than monohull boats. Dramamine works! A pleasant reminder to take them before getting on board if you’re prone to motion sickness.
• Cancellations! If you need to cancel a tour, all tour companies provide full refunds. Check when you’re booking as cancellation windows differ. Some allow cancellations 24 hours in advance, while others allow 72 hours.

Jordan’s Hot Take on Kaanapali Sunset Cruises:
You can’t beat the convenience and tour options if you’re staying in Kaanapali. We always recommend to friends and family to “get on the water” when visiting Hawaii, and a sunset cruise does just that. At 2 hours long, these are fast, fun, and delicious ways to have a memorable Maui experience. We love these sunset tours! We love walking out of some of the Best Family Resorts on Maui and onto a sunset dinner cruise.

Details Before You Book a Kaanapali Sunset Cruise

Feel free to jump down to our list of Kaanapali Sunset Cruises below as this is a long section! I put it before the reviews as it helps answers questions about the tours that are specific to Kaanapali Beach.

If this is your first time visiting Ka’anapali and Maui, here are a few common questions and concerns we receive. 

Kaanapali Sunset Cruises are Beach Loading

Beach loading! Kaanapali Beach doesn’t have a harbor or a pier, so Kaanapali tours depart from the beach. The catamaran will drive up to the surf break.

Catamarans will have a staircase to the beach with handrails for safe loading. Waves will be splashing at your feet in about 12 inches of water.

Expect to get wet when loading from the beach. Water may come up to your knees. For a sunset sail, you may need to roll up your pants or hang onto your dress. We do not recommend wearing jeans or other tight pants (see our Hawaii packing list). In our experience, sandals and shoes are removed and collected on the beach in a bin. Shoes are not worn on board. Electronics should go in a bag in case they get wet in your pockets.

Kaanapali sunset cruises are not recommended for guests with mobility issues. We recommend taking a tour from Ma’alaea Harbor if you have mobility issues. Sail Maui offers Molokini Crater, Sunset Sails, and Whale Watching Tours from Ma’alaea Harbor. Plus, we have 10% off with Sail Maui! Click here for more information on Sail Maui Tours from West Maui.

We have never had an issue with beach loading tours in Hawaii. The captains are experts at bringing the boats as far up the beach as possible. The crews provide a quick safety talk on the beach as everyone is lined up for an organized and quick loading. The biggest safety issue is usually hitting your head as you climb the stairs.

Watch our videos below as we share how our family boards from Kaanapali beach. You will have a better understanding of what to expect.

Do You Go Sailing on Kaanapali Sunset Cruises?

Yes! They will put up the sails as they sail just offshore Kaanapali for the sunset. It makes for great pictures and a peaceful cruise. 

Sailing will depend on the conditions, so it is not guaranteed. The crew understands that choosing a catamaran means you want to sail, so that is what they will try to do!

Parking for Kaanapali Sunset Cruises

One of the best parts of staying in Kaanapali Resorts is the tours leaving from your hotel’s beach. For folks who are staying down the road in Napili or Kapalua, parking may be top of mind when booking a Kaanapali tour. 

Your Kaanapali sunset tour company will provide information on where to park in Kaanapali Resorts upon booking your tickets and in the email you receive to confirm your reservation. We always save the parking information in our itinerary and make sure we have the Google Map directions available.

You can park at hotels for tours that leave in front of resorts, like Trilogy leaves from the Kaanapali Sheraton, and Teralani leaves from the Outrigger Kaanapali Beach Resort. The tour company may provide a discounted rate for parking.

Most Kaanapali tours leave from the beach in front of Whalers Village Shopping Center. This is the middle of Kaanapali, and there is abundant parking at the shopping center’s garage. The tour company may provide validated parking. It is great when they do. If they don’t, you can get your parking validated by buying something in the shopping center.

We never give up hope on finding a spot in the few public parking lots in Kaanapali Resorts. There are four public parking lots dotted along the main road lining the beach. Each lot has about 15 to 20 spots. They are small and fill up quickly! Look for the public parking signs and good luck!

How Much to Pay for Kaanapali Sunset Cruises:
Kaanapali sunset cruises range from $108 to $147. The price difference usually comes down to the type of food served (pupus, buffet, table service) and drinks offered.

Reviews: 6 Kaanapali Sunset Cruises

Here we go, the complete list of Kaanapali sunset cruises! I’ll call out the details that make the tours different. It could be that tours run daily, kids are free, or that they have live music. 

You can click the buttons for more details on the tour and to book it. In the spirit of complete transparency, I will put an asterisk next to the tour companies with which we are partnered. That means we earn a small commission at no cost to you when you book a tour on our website. Mahalo for your support!

We provide costs for the Kaanapali sunset cruises. Prices are subject to change! We do our best to keep this article updated. Click the booking buttons to get the latest price and information on the tour quickly!

We share the price per person, before taxes and fees.

Sunset cruise departure times change slightly throughout the year to coincide with sunset. Departures are usually from 4:30 to 5:30 PM.

Sea Maui* for Well-Priced Luxury Catamaran

Besides having a clever name, Sea Maui has two large, comfortable, and never crowded catamarans and two tour options. 

We are listing them first because they offer the most popular tour types on wonderful catamarans and at a good price.

We have gone out on Sea Maui twice! Once for their whale watching tour and another time on their Premium Sunset Dinner Cruise.

Why we like them: They offer a luxury catamaran experience at a good price. Their catamarans have netting in the front with bean bags. Sit up front or on the benches as the crew gets drinks for you. The boat does not feel crowded or like a booze cruise. They depart from central Kaanapali, and they validate parking!!!

• Drawbacks: Their food is average, tasty, but nothing to write home about. 
• Passenger Size: 48 guests
• Boat Type: Catamaran
• Departure: In front of Whalers Village Shopping Center. Meet at their kiosk that is beachside, near Leilani’s restaurant. 
• Parking: 4 hours of parking validation at Whalers Village! That is a nice savings.
• Loading: Beach loading catamaran
• All Ages are Welcome!

Premium Sunset Dinner Cruise

• UNIQUE: Includes live music on Wednesdays and Saturdays
• Tour Price: $147 Adult, $124 Teens 13 – 20 yrs old, $113 Children 3 – 12 yrs old, Free 0 – 2 yrs old
• Duration: 2.5 Hours
• Availability: Daily
• Included: Dinner and complimentary bar
  • Dinner menu:
    • Grilled Salmon with Teriyaki
    • Soy-Braised Short Rib with Red Wine Sauce
    • Kung Pao Chicken
    • Ceasar Salad
    • Mixed Seasonal Vegetables
    • Fingerling Potatoes
    • Dinner Rolls (gluten)
    • Truffles

Watch our experience on Sea Maui’s Premium Sunset Dinner Cruise! From beach loading to dining, here is a quick video of our experience on this tour.

Sunset Cocktail Cruise

• UNIQUE: Includes live music on Tuesdays and Thursdays
• Tour Price: $108 Adult, $85 Teens 13 – 20 yrs old, $74 Children 3 – 12 yrs old, Free 0 – 2 yrs old
• Duration: 2 Hours
• Availability: Daily
• Included: Heavy appetizers and complimentary bar
  • Appetizer menu:
    • Crispy Pork Sliders
    • Chicken Parmesan Salad
    • Crunchy Asian Slaw
    • Fried Chicken with Unagi & Spicy Chili Garlic Aioli

Trilogy for Luxury Catamaran

The Trilogy Family (Coon Family) has become an institution on Maui. Grandpa started the business in the early 70s when he moved to Maui with his family. They were the first ones to operate tours to Lanai for day trips. The third generation has continued the family business, but with a range of luxury sailing catamarans and various tour offerings. Here are their Kaanapali sunset cruises.

West Maui has Trilogy for a luxury experience, and South Maui has the Kai Kanani family. Kai Kananai has our favorite Molokini Snorkel Tour and Adventure Sunset Sail.

I heard a story about Trilogy during the Lahaina fires. A family member drove to Lahaina Harbor to save their newest catamaran. He tossed his truck keys to a family who was trapped at the harbor. He then navigated the catamaran out of the harbor by compass as the smoke was too thick to see.

• Why we like them: This is a luxury tour on a catamaran, including food, drinks, and the crew. Trilogy differentiates itself with its service and quality. The food is served; no buffet lines here.
• Drawbacks: It is hard to think of one! It is the priciest sunset tour on this list, but you get what you pay for. I’m surprised they don’t cover parking at the Sheraton.
• Passenger Size: 40 to 50 guests
• Boat Type: Catamaran, 55 ft – 65 ft
• Departure: Sheraton Kaanapali Hotel, check in at Sheraton’s Beach Lawan
• Parking: Sheraton parking is $15 per day, no discount is offered
• Loading: Beach loading catamaran
• All Ages are Welcome!

Deluxe Kaanapali Sunset Sail

• Tour Price: $119 Adult 18+, $119 Teens 13 – 17 yrs old, $80 Children 3 – 12 yrs old, Free 0 – 2 yrs old
• UNIQUE: Have appetizers at personal two-top tables
• Duration: 2 Hours
• Availability: Daily
• Included: Plated appetizers and complimentary bar
  • Kula Cherry Tomato & Mozzarella Skewer
  • Hummus with cucumbers and carrots
  • BBQ Chicken Skewer
  • Kalua Pulled Pork Sliders with Coleslaw on a Sweet Hawaiian Roll

Make a day out of visiting Kaanapali with one of these Kaanapali tours! Watch our video below where we explore West Maui for the day. We squeeze in one of these Kaanapali beach loading tours!

Gemini* Catamaran Sunset: Best Priced Dinner Sail

The next two Kaanapali tours, Gemini and Teralani, are catamaran sunset tours. You will see their fleet of catamarans moored offshore Kaanapali Beach. These are the closest you will get to a value tour on Maui.

If you’re looking for a good price without the bells and whistles of a luxury catamaran tour, then this is the tour company for you. As they load in front of the Westin, this is a good option for Maui Westin Resort and Spa guests.

• Why we like them: It is a good price for the sunset cruise they offer. The boarding location is conveniently located on central Kaanapali Beach.
• Drawbacks: The catamaran can feel crowded.
• Passenger Size: 49 guests
• Boat Type: Catamaran
• Departure: Kaanapali Beach, in front of the Westin Maui Resort and Spa
• Parking: Whalers Village Shopping Center, validated parking is not offered.
• Loading: Beach loading catamaran
• All Ages are Welcome!

Sunset Dinner Sail

• Tour Price: $127 Adult 18+, $107 Teens 13 – 17 yrs old, $97 Children 3 – 12 yrs old, Free 0 – 2 yrs old
• Duration: 2 Hours
• Availability: Daily
• Included: Buffet dinner and complimentary bar
  • Dinner menu:
    • Hawaiian Style Teriyaki Chicken (Gluten Free)
    • Rice and Quinoa Pilaf (Gluten Free)
    • Crudite Platter with Mediterranean Hummus (Gluten Free)
    • Rolls
    • Maui Style Potato Chips
    • Chocolate Chip Cookies

Kaanapali Resorts History
The word “kāʻanapali” means “the divided hill.” Since its beginnings as an ancient Hawaiian village, Kāʻanapali has been a spiritual and recreational home for generations of Hawaiians. The current site of the Royal Lahaina Resort was a thriving fishing village called Keka’a. 

Amfac, Inc. first built the resort area in the 1960s along a mile stretch of beach. Many more hotels and condos have been built since then. Today, Kaanapali is a planned resort community of 1,161 (2020 census) full-time residents. The resort area is 4.9 square miles and is divided into South and North Kaanapali.

Teralani* Catamaran Sunset Tours

Teralani is similar to Gemini in terms of cost and experience on a large catamaran. Their brightly colored boats line Kaanapali Beach. On board their three, 2005-built, 65-foot-long catamarans, you will find plenty of shade, tables for two people, and a hard-working crew.

Compared to Gemini, Teralani has a more local and diverse menu on their sunset dinner sails. Pick the tour that’s right for you!

• Why we like them: With multiple boats and tours going out daily, they are a great option for a quality catamaran sunset tour at a good price.
• Drawbacks: The large tour company lacks the personal touch and feel of the smaller operators.
• Passenger Size: 49 guests
• Boat Type: Catamaran
• Departure: Kaanapali Beach, in front of the Outrigger Kaanapali Beach Resort
• Parking: $8 at the Outrigger Beach Resort, discounted fare is for the first 5 hours
• Loading: Beach loading catamaran
• All Ages are Welcome!

Holo Holo Sunset Cocktail Sail 

• Tour Price: $110 Adult 13+, $100 Children 6 – 12 yrs old, $70 Toddlers 0 – 5 yrs old
• Duration: 2 Hours
• Availability: Daily
• Included: Appetizers (pupus) and complimentary bar
  • Appetizer menu:
    • Vegetable crudité platter
    • Cheese and crackers
    • Passed appetizers: mozzarella skewers, teriyaki meatballs, coconut crusted shrimp
    • Brownie

Kaanapali Sunset Dinner Sail 

• Tour Price: $140 Adult 13+, $110 Children 6 – 12 yrs old, $80 Toddlers 0 – 5 yrs old
• Duration: 2.5 Hours
• Availability: Daily
• Included: Appetizers (pupus), dinner, and complimentary bar
  • Appetizer menu:
    • Mozzarella skewers and teriyaki meatballs
  • Dinner menu:
    • Curry-marinated fish with Kumu Farms salsa
    • Beef short rib
    • Glazed tofu with Kumu Farms salsa (vegetarian option)
    • Sides: salad, Molokai sweet potatoes, green beans
    • Brownie

After all this talk about sunset tours and delicious menus, why not dive into more of Maui’s dining?
– Dinner on the Beach in Maui: Private Dining and Beachfront Restaurants
– 5 Best Maui Food Truck Parks
– Don’t Miss the 15 Best Restaurants in Wailea & Kihei (by category!)
– 6 Best Wailea Happy Hours
– Mama’s Fish House: Is the Best Time Lunch or Dinner?

More to Do in Kaanapali!

As you can tell, we enjoy Kaanapali tours. From whale watching to a sunset dinner sail, you won’t regret squeezing a tour into your Maui itinerary.

Check out our video below on more things to do in Kaanapali and West Maui. We lived in Lahaina, so West Maui was our backyard. It is home to our favorite Maui beaches, hikes, food truck parks, and snorkel spots. 

A tour that few people know about is stargazing from the West Maui Mountains. Check out this stargazing tour in Ka’anapali! We had fun and it was educational.

For even more, see our article on Things to Do in Kaanapali!

Once your tour is booked, you can finish your Maui trip planning with our Maui Wayfinder Itinerary. Let us share perfectly planned days across the island so you can enjoy the sun and the beach. We did the hard work for you. Learn more below!

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