Captains Sunset Dinner Sail

Join the Captain on Trilogy's luxury sailing catamaran for an evening of fine dining with an unbeatable view.

We went on the Captain's Sunset Dinner and let me tell you, it was one of the most amazing experiences we had in Maui. The staff, service, boat ride, music, food, views… I mean EVERYTHING came together so beautifully like a symphony. We really admired the staff and their teamwork and everything they did to make this experience worthwhile. Our hats off to the chef as well, the food was absolutely divine.
My wife and I took the Sunset Dinner Cruise and had a great time! The Captain picks the perfect spot to turn off the engine, open up the sail, and follow the sun as it sets. My wife is vegan and I'm vegetarian, and they did a great job accommodating. The food was fantastic, especially the dessert which I was too full to finish! Great trip, great food, great crew!

A four-course dinner with an unbeatable view! 2-top tables are set for intimacy &  comfort; a private restaurant feel without the crowds aboard our spacious sailing catamaran.  As you are escorted to your table, the evening begins with cocktails and sailing along Maui's scenic coast.  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 your chef-prepared entrée. This is no ordinary dinner! After the sun sets, enjoy starlight sailing and after-dinner drinks.


A Look at your tour

first class dining


• Baked Breadsticks dusted w/Ala'e Sea Salt, with Lilikoi Butter
• Smoked Salmon, Crispy Pita & Fresh Dill
• Cucumber Slices topped w/Maui Onion Cream Cheese
• Tataki-style Beef Tenderloin on Crostini

Salad:Trilogy Caesar Salad w/Blue Cheese Vinaigrette

Dinner Options (one per guest):
• Pan-Seared Rosemary & Garlic Crusted Top Sirloin Steak
• Gourmet Chicken Breast w/Citrus Zest
• Fresh Island-Caught Sautéed Fish, w/Lemon Caper Butter Sauce
• Portobello Mushroom Penne Pasta w/Thai Basil Marinara

Dessert: Trio of Lilikoi Cheesecake, fresh Strawberries & Dark Chocolate Truffle

All dinner options (except pasta) served with a swirl of Molokai Sweet & Buttermilk Mashed Potatoes and Sautéed Seasonal Vegetables. 

drinks & cocktails

Feel the aloha vibes as our Crew serve up a wide variety of alcoholic and non-alcoholic beverages--a little tasty something for everyone on this Dinner Sail.

Our Premium Bar consists of:

• Kona Brewing Co. Seasonal Lager
• Kona Brewing Co. Big Wave Golden Ale
• Sauvignon Blanc ~ Prosecco ~ Pinot Noir
• Moloka'i Mule- Our thirst-quenching twist on the classic Moscow Mule
• Lana'i Tai- A Mai Tai done the Trilogy way, topped with a float of Potters Tropical Breeze Special Dark Rum

Non-Alcoholic Beverages:
Coke, Diet Coke, Ginger Ale, Pineapple Juice, POG Juice, Soda Water, Chilled filtered Water

NOTE: Guests must be 21+ to enjoy our bar beverages.

itinerary & departure

Our Captain’s Sunset Dinner Sail departs from two locations, dependent on the day of the week. Between Oct 1st-Feb 28th, the sail time is 4:45pm-7:15pm, and between Mar 1st-Sep 30th, the sail time is 5:15pm - 7:45pm.

MAALAEA HARBOR: WEDNESDAY and FRIDAY, the Dinner Sail departs from Slip #62 at Ma’alaea Harbor.  Check-in time is 15 minutes prior to departure time. Paid parking is available within Ma'alaea Harbor for .50c/hr; please pay for parking prior to checking in. If using a GPS, you can enter this address for directions: 11 Ma'alaea Harbor Rd, Wailuku, HI 96793.

LAHAINA HARBOR: On THURSDAY, SATURDAY, and SUNDAY. the Dinner Sail departs from Lahaina Harbor, at the main loading dock by the Lighthouse.  Check-in time is 15 minutes prior to departure time. There is free 3-hr parking along Front St (first come, first serve). If you desire a secure lot (pay-for-parking), we recommend the Republic Parking Lot on Dickenson Street in Lahaina - look for the "Trilogy Parking" sign. If using a GPS, please use this address: 155 Dickenson St, Lahaina, HI 96761.

Included on this tour
  • Chef prepared and plated Four-course Dinner:
    • Appetizers
    • Salad
    • Entrée
    • Dessert
  • 21+ yrs: Premium Bar
  • Sodas, Filtered Water, Juices, Mocktails
  • Sailing & Stargazing (post sunset)
  • Whale watching Dec-April
  • Print or view the tour fact sheet 
  • NOTE: This tour is only available for guests 18 and over.
  • NOTE: We recommend you bring a light jacket or sweatshirt. 

Our Trilogy family takes seriously the responsibility of supporting our local Maui community and has a strong commitment to preserving our ocean and island environment. Learn more about Trilogy's involvement with the Community & Environment.

Trilogy adheres to DOLPHIN SMART Guidelines: All photos and videos were taken while viewing from a responsible distance. The dolphins or whales in these photos and videos approached the boat while the engines were in neutral or off. All underwater photos and videos of dolphins and whales were taken with a remote device while following guidelines for responsible viewing. More information on Dolphin SMART.