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

Departure from Lahaina on Thursday, Saturday and Sunday or Ma'alaea on Wednesday and Friday only.
Time Mar - Sep (Summer):  5:15 PM
Oct - Feb (Winter): 4:45 PM
Duration 2.5 hours
Lahaina on Thursday, Saturday and Sunday or Ma'alaea on Wednesday and Friday only.

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 13, 2024 -

Tammy B.

Today was an 11 out of a 10 day (as Captain Riley would say) on the Trilogy II snorkeling excursion out of Ma'alaea Harbor. Our 1st stop was the sacred...  more

- Mar 19, 2024 -

Mark M.

We had a fantastic time. The Captain-Turtle-as his crew were outstanding and outgoing. The food was better than expected. The humor was nonstop. Highly...  more

- Mar 18, 2024 -

Janice Z.

We sailed for a dinner cruise on Trilogy 1 with Capt Zach and First Mate Becca. Had an amazing time. Loved the crew - great service and the food was...  more