Table Of Content
We started with a yummy caesar salad before moving onto our pre-chosen steak entrees (they also have a fish and vegetarian option), accompanied with mashed potatoes and mixed vegetables. Considering this meal was prepared on a boat, I was really impressed with the level of detail they put into the experience. During this cruise, you’ll be treated to stunning panoramic views of Haleakala, West Maui, and Kaho‘olawe. Their personal two-top outside tables set the stage for a romantic and intimate evening, far from the crowded restaurant scene. Trilogy Excursions regularly gives back to our local Maui County community. Each year they sponsor events on Lanai and Maui for the less fortunate and ocean clean up.
Important activity information
Departing directly from Ka’anapali Beach, climb aboard our luxury sailing catamaran and escape the crowded restaurants onshore. Scan the QR code at the harbor, enter your license plate number and pay. I’ve been on several boat tours on Maui, and Trilogy’s table service was a nice touch, compared to the typical buffet-style found on most others. Our table neighbors had actually been on a kayak tour with my boyfriend the day before, and by his recommendation, decided to whale watch from a boat as well.
Trilogy – Deluxe Ka’anapali Sunset Cocktail Sail
As you relax and take in the romantic sunset views of Kaho’olawe and Lana’i, enjoy pre-plated appetizers and a premium bar with a wide variety of cocktails and beverages. The Captain’s Mule offers a refreshing twist on the classic Moscow Mule, with options to customize your choice of spirits. For an up close & personal look at Maui’s marine wildlife, we also offer an optional SNUBA upgrade for any guest 8yrs and older (space is limited).
Maui Sunset Sail Tour Restrictions
Slip #62 is located on the break-wall (ocean) side of the harbor. Here at Trilogy our goal is to make your Trilogy Adventure in Paradise both educational and entertaining, but above all, we are committed to making your day with us the safest day of your vacation! All our vessels are USCG (United States Coast Guard) certified and ocean tested sailing catamarans that we designed and/or built ourselves specifically with you in mind. Your safety and comfort were critical considerations in the design and building process. Every vessel, as well as all our land based operations, carry emergency oxygen as well as Emergency AED’s.
We serve a tasty spread of plated appetizers that are sure to satisfy even the most discriminating gourmet. Christened Trilogy in 1971, their new 50′ sailing trimaran carried them for two years from Alaska to Mexico, Central & South America, the Galapagos Islands, and eventually, the South Pacific. It was there they decided, because of limited funds, to sail north to Hawai‘i and work until ship stores were replenished, before continuing their “around the world” Odyssey. But, as Jim and Rand are fond of recounting, they not only fell in love with the islands, they fell in love with a couple of island girls as well and settled instead on the island of Maui. In the 1920’s, two brothers, Eldon and Afton Coon, built a fishing boat in Port Townsend, WA, and set sail for Alaska.
The Lana’i Tai, a delicious cocktail, combines Mango Rum, Orgeat, and more for a delightful taste of the tropics. Or, opt for a Good Ol’ Fashioned or a Lahaina Sunrise to suit your preferences. Experience a romantic Deluxe Ma’alaea Sunset Sail on board Trilogy Excursions.
In addition, our captains and crew maintain current certifications in CPR and First Aid and adhere to USCG regulations. Also, all vessels carry slicker gear for each passenger in the event that the wind and seas kick up during a passage. If you can keep dry here in the tropics you will usually stay warm and comfortable as well.
This Dinner Cruise is on a large luxury sailing catamaran with a small passenger count and seating is set for couples only! Trilogy’s ‘Captains Dinner’ is your best choice for a romantic Hawaiian Dinner Cruise on Maui. Last month I hopped on Trilogy’s Sunset Dinner Sail, which departs weekly from Maalaea Harbor on Mondays, Wednesdays, and Fridays.
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Book this tour
When it comes to things I enjoy, boat rides on the ocean are generally toward the top of the list. Add in whale watching during sunset, an open bar, a three-course dinner, and a random assortment of Hawaiian and 80s tunes, and it’s essentially a perfect storm of awesomeness. Check-in time is 15 minutes prior to scheduled departure time, at the loading dock. Check-in time is 20 minutes prior to scheduled departure time. Enjoy Romance, Cocktails, and a Hawaiian Sunset over the Pacific Ocean on Maui’s newest Sunset Dinner Cruise. Our Romantic Sunset Dinner Cruise is a step above most Maui Dinner Cruises!
As you take in a breathtaking Maui sunset, our Captain will also share stories of our local history and marine life. Sunset dinner sail tours last approximately 2.5 hours, cost $129 per person, and are only open to guests 21 and over. After lunch, we’ll raise the sails and head back to the beach! For guests 21+ (with ID), two adult premium beverages are included on the return sail, as well as sodas, juice, and filtered water. The evening begins with cocktails and sailing along the scenic and tranquil Maui coastline. Enjoy the special four-course dinner as the sun sets on another beautiful Maui day and the evening continues under the starlight with after-dinner drinks.
Guests dine at private two-top tables outdoors and enjoy a scrumptious spread of plated appetizers to satisfy even the most discerning gourmand. Feel the aloha vibes as the crew serves a wide variety of alcoholic and non-alcoholic beverages, offering something tasty for everyone on this Sunset Sail. Relax as world-class Trilogy Crew members serve a variety of mouthwatering pupus, signature cocktails, and share their knowledge of Maui’s history and marine life. Trilogy Excursions is the oldest family-owned and operated activity and sailing business in Maui.
Connected through a light harness, you can then dive down up to 20 feet and enjoy up-close-and-personal views of our amazing reef and marine life! Please contact for availability of SNUBA on our Discover Molokini and Discover Lana’i tours. Please watch this quick video showing our beach-loading process during medium shore break.
Guest dine on a chef-prepared gourmet 4-course dinner at intimate two-top tables seated on deck. The courses are fixed with exception to your entree, which you must select when booking. Lana’i Tai – A Mai Tai done the Trilogy way – Mango Rum, Orgeat, Fresh lime, Elixir G ginger syrup, pineapple juice and a float of Potter’s Dark Rum.
Please keep in mind that beach loading requires a certain level of physical fitness. Guests with injuries or disabilities which impede mobility may find beach loading too difficult or strenuous. We recommend parking at the Sheraton parking structure ($10 paid by guests only if validated by Trilogy) however guests may park anywhere they’d like. After checking in with our Crew, we will walk to board the boat in front of the Outrigger Ka’anapali Resort where there is an ingress zone. Please arrive 30 minutes prior to tour departure to Check-in.
