Captains Sunset Dinner Sail

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

This tour departs at 4:45 pm

Steak Entree


Fish Entree


Chicken Entree


Vegetarian Pasta


Adults (18+) only for this tour!



Only 4 Left!

Trilogy II

64' Custom SeaRunner/Cutter rigged sailing catamaran

Built: 2010, Schooner Creek Boat Works, Portland, OR
Sails: 1,950 sq/ft working sails
Specs: 64' x 32', Draft @ DWL 5'
Capacity: Normal working capacity 60 passengers
Crew: Captain, 1st Mate, 2nd Mate, Deckhand
Other Info: Twin 350 hp Yanmar turbo diesel full electronics, covered cabin, netting forward & aft, two heads, large galley, cushioned seating inside and outside.

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Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort; a private restaurant feel, without the crowds, aboard Maui’s newest sailing catamaran. 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. From there on, 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 is preparing 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 our executive chef, each course has been thoughtfully put together using fresh, local ingredients, creating a masterpiece for your taste buds. Pair that with a glass of Prosecco, outstanding service, and postcard-worthy scenery, and you have a dinner you’ll remember for a lifetime. 

Items are subject to change without notice 

- Freshly baked breadsticks dusted with Ala'e Sea Salt with Lilikoi Butter
- Smoked Salmon "Wedge", Crispy Pita & Fresh Dill
- Cucumber topped w/
Maui Onion Cream Cheese
Tataki-style Beef Tenderloin on Crostini 

Trilogy Caesar Salad
 with Blue Cheese Vinaigrette

Dinner Options: (Choose One)
- Pan Seared Fresh Rosemary & Garlic Crusted Top Sirloin Steak
Gourmet Chicken Breast with Citrus Zest
- Fresh Island-Caught Sautéed Fish with a Lemon Butter Caper Sauce
- Penne Pasta Tossed with Thai Basil Marinara & Topped With Portobello Mushroom (Vegetarian)
- All dinner options are served a swirl of Molokai Sweet and Buttermilk Mashed Potatoes and Sautéed Seasonal Maui Vegetables, with the exception if the Vegetarian Penne Pasta.

Trio of Lilikoi Cheesecake, Fresh Strawberries, and Dark Chocolate Truffle

A selection of non-alcoholic beverages and chilled filtered water are available.

Premium Bar: 
For guests ages 21 years and up*, we offer an open bar which includes: Moloka‘i Mule, Lana‘i Tai, 
Kona Brewing Co.'s Big Wave Golden Ale & Seasonal Lager, Prosecco, Sauvignon Blanc, & Pinot Noir.  
*I.D. must be present

Trilogy's Dinner sail is available for Adults 18 years and older only

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October 1st - February 28th (Winter): Please check-in at 4:30 pm. Depart 4:45 pm and Return 7:15 pm 
March 1st - September 30th (Summer): 
Please check-in at 5:00 pm. Depart 5:15 pm and Return 7:45 pm 

This trip departs out of Ma‘alaea Harbor. If you are using GPS please use the following address: 11 Ma‘alaea Boat Harbor Road, Wailuku, Hawaii 96793. Parking is available along Ma'alaea Harbor and costs $.50 per hour. Please be sure to pay the meter prior to checking in. 

4:30 pm (winter) | 5:00 pm (summer) at Ma'alaea Harbor, TRILOGY II Slip #62. Ocean-side of the harbor. 

4:45 pm (winter) | 5:15 pm (summer) from Ma'alaea Harbor.

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Jacket or light cover-up. If you are not wearing deck shoes or rubber-soled shoes, we will collect your footwear at the beginning of the trip. We only accept credit cards for any onboard purchases. 


Print or view the tour fact sheet

For groups larger than 20, consider a private charter

Your Ticket Price Goes Towards

Blue Aina reef cleanup program - Trilogy parters with Surfrider Foundation to clean-up reefs around Maui
Maintaining day use mooring - For all boats in Maui county (helps save the reefs)
Eliminating overboard discharge - Trilogy is the first company in Hawaii to retrofit its boats to pump all waste onshore

Environment & Community

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