Kaanapali Sunset

Trilogy Excursions (4.7)
Watching the sun dip below the horizon as you sip fabulous Molokai Mules (our favorite) or Lanai Tais as you sail the warm tradewinds on a beautiful catamaran.
Why We Love It -  There's nothing like a Maui sunset to spark a bit of romance! This beautiful sailing catamaran features amazing food and a premium bar.

See the day set from our world class sailing catamaran!

Experience Maui's majesty as we explore the West Maui coastline surrounding Kaanapali. By far the best way to view Maui is from the ocean looking back at the breathtaking mountains and beautiful rainbows often seen in the valleys. Enjoy tasty pupus (appetizers) and an assortment of cocktails coupled with world-class service from your talented and knowledgeable Crew. So join Maui's oldest and most experienced sailing company for a personalized sunset that leaves directly from world famous Kaanapali Beach

View a unique Maui sunset aboard the safest and most comfortable ocean sailing catamaran on the water! Throughout this two-hour journey, enjoy breathtaking views, an active ocean environment, and a delicious assortment of complimentary appetizers and beverages made just for you by our crew.

Take a Maui sunset sail aboard Trilogy's safe and comfortable ocean sailing catamaran. Our sunset cruise provides the most romantic way to experience the beauty of a Maui sunset. Our chefs prepare an assortment of hot and cold appetizers that are guaranteed to satisfy the most discriminating gourmet. With breathtaking views of Molokai and Lanai, spinner dolphins and flying fish, this two-hour Maui sunset sail is relaxing, delicious, and romantic! So, join Maui's oldest and most experienced sailing company for a personalized deluxe sunset sail that loads directly from world famous Kaanapali Beach. 

Included with Tour 
  • Crew will serve a tasty appetizer spread of Kalua Pork Sliders, Teriyaki Chicken Skewers, Lobster Mango Summer Rolls, Spinach Rolls, and Vegetarian Summer Rolls. Last but not least Chocolate Brownies with a Kona Coffee Mousse topping will be served for dessert.
  • Assorted beverages and water
  • For guests ages 21 years and older*, we offer a premium bar which includes: Molokai Mule, Lanai Tai, Locally Brewed Beer, and White Wine. * I.D. must be present. 
Mar - Aug 5:00 PM
Sept - Oct 4:30 PM
Nov - Feb 4:00 PM
Monday, Tuesday, Wednesday, Thursday, and Saturday
Duration 2 hours
Location Ka'anapali Beach

Please view the cancellation policy and restrictions.

Cancellation Policy

1-4 guests:must cancel 24 hours prior to trip departure time
5-8 guests:must cancel 48 hours prior to trip departure time
9 or more guests:must cancel 72 hours prior to trip departure time
Or full amount will be charged for your tour.


Entering and exiting the boat and accessing the on-board restrooms requires ascending and descending steep stairs.  Customers must have the necessary mobility to navigate this.
No wheelchairs or walkers permitted (small or collapsable cane okay).

Frequently Asked Questions


Review Summary
show reviews  hide reviews 

- Aug 2015 -


We wanted a sunset cruise that wasn't a party barge full of loud drinking people. The Kaanapali Sunset Sail was perfect! Saff was courteous. Cruise was breathtaking. Cocktails and appetizers were served and guests were social with one another, but it was an entirely mellow and scenic experience worth taking. Highly recommend this excursion!

- Nov 2014 -


Captain Kevin, Seth and Cody provided us with an amazing sunset sailing in Maui. The commentary along with the food and drinks was outstanding. The boat was very comfortable and we were able to take some amazing photos.

- Jun 2015 -


Captain Kevin, Captain Jason, and First Mate Kendall gave us an amazing sail. Their friendly, helpful, and professional manner made us feel like we were on their own yacht. They fed us till we dropped; and made sure we had plenty of time to marinate in the beauty of a West Maui sunset. How could you ask for more. Thanks for yet another 'best evening of our trip." Byron & Pam Spradlin.

- Mar 2017 -

Alicia Dimas

Our experience was awesome! We booked a private whale watching tour for our family and everyone had a great time. All the staff were amazing, Lily did an excellent job keeping in constant communication with us with any changes and kept us informed of all of our options and even kept us in the loop regarding whether conditions that day. The crew and captain were friendly and very knowledgeable. They catered to every need we had, made sure no one had an empty drink and had enough appetizers. Only bummer of this trip was that it started raining about 30-40 mins before our trip was supposed to end, but the captain did his best to keep the tour going and get us out of rain. All of us ended up having to go below deck, but the staff kept us entertained and made sure everyone was comfortable. I would definitely book with them again!

- Apr 2017 -

Kim Holloway

Lovely adult only sunset dinner cruise. The crew was great and the food and drinks were good as well. We even saw a whale! The sunset was breathtaking!

- Mar 2017 -

Anthony Mulizio

Been out with these guys twice in 2 years and both times it was a blast. Great crews!

- Nov 2016 -

Andrew DeFilippis

My wife and I loved our scuba trip and sailing adventure. The crew did a great job of communicating with everyone and providing food and drinks the whole way. We would definitely sail with your crew again.

- Sep 2016 -

Kevin Clem

We had a great time sailing with Trilogy and would recommend them highly. Not only were the two snorkeling stops top notch, but the food was pretty alright. Most importantly the crew, they were hands down professional, courteous and most importantly kind and friendly to the kids on-board, my son who was barely three at the time still fondly tells the tail of sailing and steering the ship.