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Trilogy departs from the Ma’alaea Harbor off the island of Maui. Your tour starts with a continental breakfast of Mom Coon’s 4th generation cinnamon rolls and chilled tropical fruit cup, complimented with Kona coffee, hot tea, hot cocoa, POG or pineapple juice. Please pay via the digital parking kiosks (QR Code) for parking prior to checking in. Trilogy is not responsible for cars that are towed due to a parking error.
WEST MAUI SNORKEL
Enjoy stunning panoramic views of Haleakala, West Maui, and Kaho‘olawe on this two hour sunset sail. Please note you will be loading directly from the beach, through the surf zone onto the boat, and you will get wet! This is a barefoot charter and footwear will be collected prior to departure. The staff did a tremendously good job making it feel like a special event, which of course for us it was. They never gave the impression that it was just another night on the water.
SUNSET SAIL
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.
Trilogy Sunset Dinner Sail Review
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.
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They have shaped Maui sea activities into what it represents today. Since founded, Trilogy has expanded its offering to include just about everything you can imagine. From whale watches, Lanai and Molokini snorkeling, and Maui sunset cruises, Trilogy has an adventure for everyone. Trilogy has the largest fleet of sailing catamarans on Maui, each one represents their name – excellence.
TRILOGY DELUXE KAANAPALI SUNSET SAIL
Besides having a crew member to lead guests on snorkeling tours of the reef, you’ll also find a crew member on top of a surfboard ready and able to assist you if you in case of trouble. In addition, every snorkeler is provided with a life vest, or BCD (Buoyancy Compensator Device), regardless of their ability, and yellow float belts are also available. Some swimmers think this limits their mobility—the truth is the opposite happens.
Kaanapali Deluxe Sunset Sail
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.
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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.

Having someone to keep an eye on you (and you on them) while out in the ocean is one of the best ways to stay out of trouble. The marine life here in the islands can be mesmerizing, but by taking a moment every couple minutes to look up and verify your buddy is still nearby will ensure you both stay safe and have fun. This excursion loads directly from the sands of world-famous Ka’anapali Beach, and you will get wet when loading. Check-in time is 30 minutes prior to scheduled departure time. Almost immediately after leaving the harbor, we spotted several whales in the distance, coming up for air and pec slapping not far from the boat. One particularly frisky fella (or lady) even breached right in front of the boat.
And their attentiveness to my wife'...s dairy allergy was above and beyond! The libations were sturdy...meaning none of the cocktails were watered down. I had the Old Fashioned and the bourbon was very much in evidence and flavorful. My wife's beef was tender and tasty, a very good medium rare.
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.
Please watch this quick video showing our beach-loading process during small shore break. Please keep in mind that beach loading conditions vary and requires a certain level of physical fitness. Guests with injuries or disabilities which impede mobility may find beach loading too difficult or strenuous on higher surf days. It is recommended that guests with mobility issues and parents with small infants, book one of our many tours departing from the Lahaina Harbor.
Please be aware of where you are parking and follow the parking instructions found on the parking signs. Check-in with our Crew member in a blue shirt at Trilogy sign on grass near beach walk. Please check your confirmation for up to date check in time.
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.
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.
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