Captain Sunset Dinner Sail

Trilogy Excursions (4.6)

Join the Captain on Trilogy's luxury sailing catamaran for an evening of fine dining with an unbeatable view of the sunset. 

Tables are set for intimacy and comfort; a private restaurant setting, without the crowds, aboard Maui's newest sailing catamaran. Experience fine dining with a breathtaking view!

As you are escorted to your individual table, the evening begins with cocktails and sailing along the pali sea cliffs. After mooring in a protected cove, the first course is served. Our crew are quick to accommodate your every need and will serve your remaining three courses including an entrée of your choice that our onboard chef prepares in the galley. Dessert and drinks are enjoyed as the sun sets on another beautiful Maui day and the evening continues with music under the stars.
This is no ordinary dinner! Under the direction of executive Chef Bailey, each course has been thoughtfully put together using fresh, local ingredients, creating a masterpiece for your taste buds. Pair that with a glass of champagne, outstanding service, and postcard-worthy scenery, and you have a dinner you'll remember for a lifetime.

Captain's Sunset Menu
  • Appetizers - freshly-baked breadsticks dusted with Ala'e Sea Salt with Lilikoi Butter,  Smoked Salmon "Wedge", Crispy Pita & Fresh Dill,  Maui Onion Cream Cheese Topped Cucumber, Tataki-style Beef Tenderloin on Crostini 
  • Salad - Trilogy Caesar Salad 
  • Dinner Options - (Pick One) Pan Seared Fresh Rosemary & Garlic Crusted Steaks, Wild Caught Mahi-Mahi Sauteed and topped with a Lemon Butter Caper Sauce, Seasonal Vegetarian Pasta *All served with sauteed vegetables and roasted garlic mashed potatoes. 
  • Dessert - Trio of Lilikoi Cheesecake, Fresh Strawberries, and Dark Chocolate Truffles 
  • Beverages - Assortment of non-alcoholic beverages
  • Premium bar - For guests ages 21 years and up*, we offer an open bar which includes: Moloka'i Mule, Lana'i Tai, Maui Brew Co.'s seasonal beer, Big Wave Golden Ale, Chardonnay, Cabernet Sauvignon & Rosé.  *I.D. must be present

Time Mar - Sep (Summer):  5:15 PM
Oct - Feb (Winter): 4:45 PM
Duration 2.5 hours
Lahaina or Ma'alaea

Please view the cancellation policy and restrictions.

Cancellation Policy

1 - 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.

Last Minute Bookings

Please be aware that these bookings are subject to confirmation. If this is a same-day or next-day booking, there is a reasonable chance this will not be confirmed. For bookings that are confirmed, there will be no cancellations or refunds.


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
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- Mar 2016 -


Booked the Captains Dinner Sail for our first night on the island as a way to relax after a long flight the night before. To be honest, I expected things to be like most sunset dinner cruises, you know, the sunset is the big draw, the boat is usually marginal, and the food is in last place and only mildly filling at best. This was DEFINITELY not like that!! First, the boat, Trilogy II, is a beautiful larger catamaran that is very well kept. Our Captain, Brian, is extremely knowledgeable and capable in every way. He and the entire crew were extremely friendly, yet exude an air of confidence should anything happen while at sea. As you should always know in Maui, during whale season, never take just a whale watching cruise. Take a cruise such as a dinner or sunset cruise, because they all have a great opportunity to become a whale watching cruise. The cruise did just what I stated above. After just a short time out from the harbor we quickly began to see whales that did not disappoint. The food on this cruise was nothing less then phenomenal. It was culinary delight made by a first class chef and served at a table for two on the deck. First a wide selection of appetizers that rival those found at any great restaurant. The bar is an open bar with an endless supply of adult beverages that keep coming as long as you ask. next is bread with the tastiest butter I have ever had and a dinner salad. The entree is top notch and it is easy to forget you are on a sunset dinner cruise. We had the steak entree and it did not disappoint. Cooked to perfection and one of the best I have ever had. Then dessert followed which was just as good and all while watching the sunset over the pacific with the occasional whale breach, blow, or roll. My wife and I highly recommend this sail while in Maui, and let the crew know they made an impression on a couple from Florida. Most importantly, if whales are around, don't forget to ask for the "whale karaoke". Hearing all the whales within a 5-mile radius of the boat is something you don't want to miss.

- Feb 2016 -


From the moment we stepped on the catamaran, it was clear we were in for a special evening. The crew were friendly and welcoming. Due to the smaller number of guests, we were able to get acquainted and enjoyed getting to meet people from around the world. The dinner was excellent and nicely served. With the beautiful evening and lots of whale activity, it was everything you could hope for in Sunset dinner cruise.

- Oct 2015 -

Kim S

One of the best dinner cruises we have enjoyed. The catamaran was very comfortable. Service was absolutely awesome, and the experience was unforgettable. We celebrated our 30th anniversary, and they went out of their way to make this a special occasion. My husband ordered the fish - I ordered the steak, and both meals were excellent. Five course dinner was more than we expected. Highly recommend!


Laurie G.

Book ASAP! That's really all you need to know. A really special experience from the moment you board the vessel and receive a friendly greeting and a...


Cynthia R.

Awesome 5-star experience. You Must go! Breathtaking views! Excitement of sailing! Snorkeling on an idyllic bay on Lanai! Great food and drinks! Go! This is...


David F.

The 5 Star Reviews Are Accurate! I found these guys on yelp a few years ago, and booked them on a snorkeling tour to Lanai. One of the best excursions of...


Kristen B.

We had a great time on our sail to Lanai with trilogy. I really wanted to give this five stars because the sailing crew was high energy, provided great...