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 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
Pineapple-Smoked Chili Braised Short Rib with Shoyu Demi Sauce
Guava Brined Huli Huli Roasted Chicken
Miso Honey Baked Mahi Mahi
Market Vegetable Green Curry with Steamed Jasmine Rice (Vegan, Gluten-Free, Dairy-Free)
Entrée Options
Guests may pre-select one entrée:
Miso Honey Baked Mahi Mahi
Pineapple-Smoked Chili Braised Short Rib with Shoyu Demi Sauce
Guava Brined Huli Huli Roasted Chicken
Market Vegetable Green Curry with Steamed Jasmine Rice (Vegan, Gluten-Free, Dairy-Free)
Sides
Layered Mash Potatoes with Golden and Purple Sweet Potatoes, Butter, Coconut Cream, and Sea Salt
Harissa Roasted Carrots with House-Made Harissa
Ginger-Shoyu Braised Bok Choy
Dessert
Dark Chocolate Mousse Parfait with Vanilla Bean Chantilly Cream and Fresh 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.