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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- Nov 2018 -


We did the captain’s dinner cruise for our final night in Maui. What a treat! The boat goes out from Ma’alea Harbor, and it basically just cruises a little ways out with no actual destination. The food was great (even split our fish/steak when we said we were sharing), our cocktails were tasty (included), and they even let us take the wheel. We highly recommend this trip for anyone looking for a romantic and unique dinner. We got great shots of Lanai, molokini, and a beautiful sunset. The star watching after dark was unreal.

- Jul 2017 -

Randy H

We had a great time with Captain Emily and the rest of the crew last night on the Trilogy dinner cruise. Captain Emily let my wife, who was taking some medication that made her stay out of the sun, sit next to her in the cockpit. The drinks were flowing, and the food was really good. The crew brings everything to you- you don't have to leave your seat. We put the sails up, and it was so relaxing. Great, great evening.

- Jul 2018 -


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...


Brandon S.

Simply the best snorkel adventure I have ever been on. The boat was amazing. The captain was hilarious. Nick and the crew were funny and helpful. The...


Nessa A.

Ok... what?! We literally JUST left our snorkeling trip with Trilogy and I couldn't wait to post a review. Their service was superb!! It is so worth EVERY...


sandy m.

On 8/28/19, we did the cruise to Lanai. The crew (Captain "Turtle" Brian; Angelo; Aquaman; Ali and the rest we're soooooo awesome!! Best trip ever! We had a...