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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- Sep 2019 -


We took the Captain's Sunset Dinner Cruise out of Lahaina Harbor. Captain Turtle and crew were our hosts. This was a repeat for us. Pros: Restaurant-quality food; adults only; super friendly staff; great catamarans; limited number of participants; great setting; sailing! Cons: Mixed drinks tasted as if they were watered-down. We've been on over 20 various Trilogy cruises. We'll be back!

- Sep 2019 -


We went on this cruise for our honeymoon. It was our special adventure for the week and it was everything I wanted. The crew and captain we’re fantastic! The food was so fulfilling and the drinks were delicious! We will definitely be back! Thanks again Captain Jim and crew for the great time!!!

- May 2019 -


Absolutely top notch! Sunset Dinner Sail was amazing. Perfect ship, delicious food, fabulous crew. Can’t say enough nice things! We’ve sailed with Trilogy 5x now and will do so again at the next opportunity. Cudos to the owners for running such a great operation. Only thing that could have been improved was the length of the sail... like maybe another 6 hours ;0). 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...


Jacqueline K.

Wow, I can honestly say this is the best excursion I've ever taken. To start was the sail over to Lanai, first we were treated with a story from the...


Patti R.

Yesterday we went out with Turtle, Chris, Kenzie, and Katie on the Lanai catamaran trip. This group of folks are really wonderful. They are fun to be with...


Eren L.

This is a must do every time I visit! The people and the environment are the perfect half day trip you're looking for. Plenty of honestly delicious food...