Introducing Trilogy’s Lahaina Captain’s Sunset Dinner Sail
Why eat dinner at a restaurant when you could dine aboard a luxurious sailing catamaran with one of the best views on Maui?
Sail along the west coast of Maui, take in the breathtaking West Maui Mountains as the sun sets across the horizon, and enjoy a freshly prepared four-course dinner surrounded by the sound of the ocean and warm tradewinds. Now, for the first time since the 2023 Lahaina fires, Trilogy is bringing sunset dinner sails back out of Lahaina Harbor.
For our Trilogy ʻohana, this return means more than adding another departure location. It marks another meaningful step forward in Lahaina’s ongoing recovery and rebuilding process. Lahaina Harbor has always been an important part of our story as Maui’s first sailing company, and being back on the water from the harbor again feels deeply special to our crew, our community, and so many returning guests who have sailed with us through the years.
Back on the Water | Lahaina Harbor
For many guests staying on West Maui, departing directly from Lahaina Harbor makes the evening feel easier and more connected to the area they love most. Whether you are celebrating a honeymoon, anniversary, special occasion, or simply looking for a memorable night on Maui, this adults-only sail offers a quieter and more intimate experience than a traditional dinner reservation.
what to expect
The Lahaina Captain’s Sunset Dinner Sail features the same elevated dining experience guests already know and love from Trilogy’s Captain’s Dinner Sail offerings. Tables are set for two aboard a spacious sailing catamaran, creating a private, comfortable atmosphere without the crowds of a busy restaurant.
As the evening begins, guests are welcomed aboard with cocktails and warm local sourdough bread served with lilikoi honey butter. From there, the crew serves a thoughtfully prepared four-course dinner featuring fresh ingredients and island-inspired flavors.
Local Sourdough Bread served alongside Lilikoi Honey Butter
Blackened Ahi Sashimi with Sriracha Aioli Honey, Guava Glazed Pork Belly with Guava Glaze and Pink Sea Salt, Golden Beet Cucumber Poke with Ginger Shoyu Marinade and Shaved Red Onion
Roasted Beet & Baby Romaine Salad with Toasted Pepita, Lilikoi Vinaigrette, Pecorino, and Sourdough Croutons
Featured Menu
Pūpū & salad Course
Blackened Ahi Sashimi: Fresh Hawaiian Ahi, Delicately Blackened and Paired with Sriracha Aioli
Guava Lacquered Pork Belly: Slow-braised Pork Belly Glazed with Tropical Guava and Finished with Hawaiian Pink Sea Salt
Golden Beet & Maui Cucumber Poke: Maui Grown Cucumber and Golden Beets Marinated in a Ginger Shoyu Dressing
Roasted Beet & Baby Romaine Salad: Roasted Beets and Crisp Waipoli Baby Romaine, Finished with Toasted Pepitas, Aged Parmesan, Herb-roasted Croutons, and a House made Lilikoi Vinaigrette
Red Wine Braised Short Rib
Surf + Turf
Market Vegetable Green Curry
Surf + Turf
Entrée Options
Guests may pre-select one entrée:
Misoyaki Mahi Mahi: Pan-seared Hawaiian mahi mahi, finished with a velvety misoyaki butter sauce.
Red Wine Braised Short Rib: Fork-tender beef short rib, slowly braised in red wine and finished with a herb demi-glaze.
Huli Huli Chicken: Roasted bone-in chicken thighs lacquered with an Upcountry guava glaze.
Market Vegetable Green Curry: Seasonal island vegetables simmered in aromatic green curry, served with steamed jasmine rice. (V, GF, DF)
Sides
Whipped Yukon Gold and Molokaʻi sweet potatoes with butter, coconut cream, and sea salt.
Maui-grown baby bok choy, seared and finished with a ginger-shoyu glaze.
Carrots roasted in a smokey & savory house made harissa
Dessert
Kuʻia Chocolate Mousse Parfait: Dark chocolate mousse crafted with Kuʻia Estate chocolate, layered with vanilla bean Chantilly cream and fresh Kula strawberries.
Drinks & Cocktails
The evening also includes Trilogy’s Premium Open Bar for guests 21+ with valid ID. Cocktails can also be prepared as Zero-Proof Mocktails.
Featured beverages include:
Maui Brewing Co. Sunshine Girl Golden Ale
Maui Brewing Co. Seasonal Seltzer
Threadcount Sauvignon Blanc
Josh Pinot Noir
La Marca Prosecco
Signature cocktails include the Captain’s Mule, Lanaʻi Tai, Good Ol’ Fashioned, Lahaina Sunrise, and the 808 Margarita — all crafted with fresh island-inspired flavors.
More Than Dinner
At Trilogy, being back on the water from Lahaina Harbor is emotional for many of us. Lahaina has always been home to generations of crew members, families, guests, and local businesses connected to the harbor and ocean.
While recovery continues across the community, evenings like this represent steady progress forward. They create opportunities to gather again, support local jobs, and welcome visitors back to Lahaina in a respectful and meaningful way.
For over 50 years, Trilogy has remained family-owned and rooted in mālama kai — caring for the ocean that continues to care for all of us.
“I always tell people the best way to see maui is to experience it from the water. When you can get a mile or so from shore and really take in the sight of the mountains- the rainbows in the valley, the sheer grandness of it all, it’s simply stunning.
Lahaina has been a place for sailing canoes for over 1000 years of years. We are a modern day iteration and continuation of the kapena (captains) who have had the privilege of sailing the waters of this beautiful and special place.”
Book Your Lahaina Sunset Dinner Sail
If you’ve been waiting for the right evening to experience Lahaina from the water again, this is it.
Join us aboard the Lahaina Captain’s Sunset Dinner Sail for an unforgettable evening of sailing, sunset views, exceptional food, and heartfelt hospitality along Maui’s west coast.
Reservations are limited and advance booking is strongly recommended.