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 8 Left!

Trilogy VI

54' sloop rigged sailing catamaran

Built: 2000, Pacific Rim Yachts, Aberdeen, WA
Sails: 1,200 sq. ft. working sails, custom spinnaker
Specs: 54' x 30', Draft @ DWL 4'
Capacity: Normal working capacity 55
Crew: Captain, 1st mate, 2nd mates as needed
Other Info: Twin 350 hp. Yanmar diesel engines, two electric heads, covered cabin, cushioned seating, large galley, netting forward, custom swim steps forward, twin swim steps aft, full electronics, AC/DC.

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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 scenic and tranquil Maui coastline. The first course is served by our crew who are quick to accommodate your every need. The remaining three courses including an entrée of your choice, prepared by our onboard chef 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 champagne, 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 w/
Citrus Zest
- Fresh Island-Caught Sautéed Fish topped 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 of 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

Parking: There is complimentary 3-hour 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 Street Lahaina, HI 96761 (across from Lahaina Coolers) 

4:30 pm (Winter) | 5:00 pm (Summer) at the Lighthouse on the main loading dock at Lahaina Harbor

4:45 pm (Winter) | 5:15 pm (Summer) at the Lighthouse on the main loading dock at Lahaina 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