Experience Maui with Trilogy Sailing Charters: Molokini, Lanai, and the Captain’s Dinner Sail.

Trilogy Sailing Charters

Introduction

Trilogy Sailing Charters is more than a premier sailing company in Maui—it’s a story of family, adventure, and a deep connection to the ocean. Established in the 1970s, Trilogy combines exceptional service, eco-conscious practices, and rich history to create unforgettable experiences. From snorkeling Molokini’s pristine waters to exploring Lanai and savoring a gourmet Captain’s Dinner Sail, Trilogy offers the best of Maui’s ocean adventures.

The Trilogy Legacy

A Family Rooted in Adventure

The Trilogy story begins in the 1920s with two brothers, Eldon and Afton Coon, who built a fishing boat in Port Townsend, WA, and set sail for Alaska. After settling in Sitka and Ketchikan, Eldon carried on the family’s adventurous spirit.

Operating a successful charter-boat business in Southeast Alaska, Eldon’s life took a dramatic turn in 1969 when a shipwreck forced him and his wife, Jeannette, to start anew. With the help of their children, they built a 50-foot sailing trimaran named Trilogy in 1971. Their journey took them from Alaska to Mexico, Central and South America, the Galapagos Islands, and finally, the South Pacific.

When funds ran low, the family sailed to Hawai‘i to work and restock supplies. However, the islands captivated their hearts. Jim and Rand Coon, Eldon’s sons, not only fell in love with Maui’s beauty but also with two local island girls. The family decided to settle on Maui, and thus, Trilogy Sailing Charters was born.

Discover Molokini

A Submerged Paradise

The Discover Molokini tour offers an unforgettable snorkeling experience at one of Maui’s most iconic destinations. Molokini Crater, a crescent-shaped volcanic islet, is home to crystal-clear waters teeming with vibrant coral reefs and marine life.

Highlights of the Molokini Tour:

  • Two Snorkel Stops: Begin at Molokini Crater and then venture to Turtle Town or the rarely explored backside of Molokini.

  • Luxury Catamaran: Sail aboard Trilogy’s spacious and comfortable 54-foot trimaran with panoramic views of Kahoolawe and Lanai.

  • Gourmet Meals: Start with a continental breakfast featuring Mom Coon’s cinnamon rolls and tropical fruit. After snorkeling, enjoy a BBQ chicken lunch served with Hawaiian sweet rolls and salad.

  • Premium Drinks: Toast the adventure with two complimentary cocktails like the Lana’i Tai or 808 Margarita.

This five-hour journey blends relaxation and exploration, offering guests the chance to connect with Maui’s underwater treasures.

Discover Lanai

Maui’s Neighboring Island

Trilogy’s Discover Lanai tour takes you to Hulopo’e Marine Preserve on the secluded island of Lanai. With exclusive access to this pristine destination, guests can snorkel, hike, and relax in one of Hawai‘i’s most beautiful settings.

Highlights of the Lanai Tour:

  • Hulopo’e Bay: Snorkel in clear waters filled with tropical fish and vibrant coral reefs.

  • Cultural Insights: Learn about Lanai’s history and ecosystem from Trilogy’s experienced crew.

  • Plantation BBQ Lunch: Feast on Kiawe-grilled chicken, fresh salads, and Hawaiian sweet rolls.

  • Sunset Sail Back to Maui: End the day with ice cream and premium cocktails as you sail home.

This full-day adventure combines relaxation, culture, and marine exploration, making it a must for anyone seeking to explore beyond Maui.

Captain’s Dinner Sail: A Gourmet Sunset Experience

A First-Class Dining Adventure

For a refined and intimate evening, Trilogy’s Captain’s Dinner Sail provides a luxurious dining experience under the stars. Departing from Ma’alaea Harbor, this two-and-a-half-hour tour combines gourmet cuisine with Maui’s stunning sunsets.

Highlights of the Captain’s Dinner Sail:

  • Intimate Dining: Two-top tables create a private, restaurant-like ambiance on deck.

  • Chef-Prepared Menu: Enjoy appetizers like smoked salmon musubi and pineapple shrimp ceviche, followed by main courses such as miso-wild honey roasted butterfish or pineapple-smoked chili braised short rib.

  • Premium Bar: Sip on handcrafted cocktails, Maui Brew Co. beers, or fine wines while taking in the ocean views.

  • Starlight Sailing: Relax with after-dinner drinks as the catamaran glides beneath a sky full of stars.

Whether celebrating a special occasion or simply enjoying Maui’s beauty, the Captain’s Dinner Sail is an unforgettable way to end your day.

Why Choose Trilogy Sailing Charters?

  • A Rich Legacy: Rooted in adventure and family, Trilogy offers a unique connection to Maui’s culture and history.

  • Eco-Friendly Practices: As a Sustainable Tour Operator, Trilogy is dedicated to preserving Maui’s marine environment.

  • Luxury and Comfort: Trilogy’s state-of-the-art catamarans and attentive crew ensure a premium experience.

  • Exceptional Culinary Offerings: From breakfast on the Molokini tour to gourmet dinners on the Captain’s Sail, Trilogy sets the bar for ocean dining.

Plan Your Trilogy Adventure

From snorkeling Molokini’s vibrant reefs to exploring Lanai’s pristine shores and indulging in a Captain’s Dinner Sail, Trilogy Sailing Charters offers something for everyone. Join Maui’s most storied sailing company for an experience that blends adventure, luxury, and history.

Book Your Trilogy Adventure Today:

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