Discover Lanai

Exclusive Discover Lanai snorkel sail

Started 46 years ago, our flagship Discover Lanai tour is sure to become your favorite day in Hawaii! Trilogy has exclusive permission to escort guests to Hulopo’e Marine Preserve (Lana’i), where you can swim, snorkel, play volleyball, hike, and participate in a guided cultural experience. Post activities, everyone gathers at the beautiful Hale o Manele to enjoy a full plantation BBQ lunch, complete with our famous Kiawe-grilled chicken. On the return sail, enjoy a cold drink, premium bar beverages, and ice cream sundaes to complete a truly memorable day.

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Molokini

Exclusive Discover Molokini Snorkel Sail

Come join Maui’s #1 sailing company as you embark on this “must-do” Maui adventure! Board our spacious sloop-rigged sailing catamarans with ample room for lounging and unobstructed views of Kahoolawe and Lanai. Our first snorkel stop is to the iconic Molokini crater* followed by a 2nd stop, usually to Turtle Town*. Your Molokini excursion is lead by seasoned Captain & Crew who guarantee to get all the little details just right to assure you and your group of enjoying a safe, fun, and comfortable day!

Trilogy Discover Ka'anapali Snorkel Sail

Exclusive Discover Ka'anapali Snorkel Sail

Our Discover Ka’anapali tour starts with a direct board from the golden sands of Ka’anapali Beach. Your adventure continues with a hot breakfast of Mom Coon’s cinnamon rolls as we sail to our first snorkeling destination, typically Honolua Bay.  Our NEW luxury sailing catamaran is comfortable and roomy, with freshwater showers, cushioned seating, and large bathrooms. This 5-hr excursion is a group favorite! Includes 2 snorkel sites*, sailing, and the friendliest Captain and Crew who will keep the food and drinks flowing, and ensure your day with Trilogy is safe and No Ka Oi!

Sunset Sails

Exclusive Sunset Sails

Whether it's a four-course dinner with an unbeatable view and nighttime sailing or simply 2-hours of friends, light pupus, drinks, and live music, Trilogy can deliver the best exclusive sunset sail your group will ever experience.  We sail out of Ma'alaea Harbor which is very convenient for those guests staying on the Wailea side of the island and Our Lahaina and Kaa'anapli locations are closer for guests staying on Maui's west side. 

Using or fleet of state-of-the-art catamarans, we can assist you with a sunset sail for any size group. From December - April, humpback whale sightings are almost inevitable.  Click the button to select from four of our wonderful sunset experiences.

Discover Oluwalu

Exclusive Discover Oluwalu Snorkel Sail

Our Discover Olowalu tour brings you to Maui’s mother reef, home to thousands of tropical fish and sea turtles right off the coast of West Maui. Enjoy your ride over on a world-class catamaran and get ready to dive into Maui’s warm waters for an uncrowded, close-up view of our reef. After your snorkel, enjoy a delicious BBQ chicken lunch (and premium bar drinks!) as you sail back to Lahaina, soaking up those breathtaking, unobstructed views of the sprawling West Maui Mountains.

Exclusice Whale Watching

Exclusive Group Whale Watch Sails from Ma'alaea or Lahaina

Set the stage for another great afternoon or evening on Maui! Highlighted by a beautiful sunset and Maui's magnificent coastal views. Today's relaxing Whale Watching Sail offers the chance to get with new and old friends, sip a cool beverage and enjoy delicious pupus while witnessing first-hand, the beauty of Hawaii’s Humpback Whales and if you're lucky, dolphins!. 

Trilogy Custom Weddings

Beautiful Custom Weddings

Over the past eight years, we’ve been able to weave together romantic sea-side vows with the class and elegance of traditional wedding elements.  Each wedding and event we coordinate is unique: from the menu selections to décor, florals, entertainment, and ceremony styles. Our coordination and planning services will give you the attention you deserve so that your vision will become a reality. Get excited to tie the knot - we are here to eliminate all the stress and uncertainties of planning a destination wedding!  

We offer unique venues on luxury sailing catamarans, and on the neighboring island of Lana’i, as well as full-coordination services for both weddings & events of all types. We work with a multitude of vendors across the island and have a preferred list of trusted individuals that we will always recommend first.