From Molokini snorkeling to a luxurious Captain’s Dinner Sail, Trilogy Sailing Charters delivers premium Maui adventures steeped in family history and ocean expertise.

Savor Maui’s most beloved dishes—kalua pork, mahi-mahi, and mochiko chicken—at top local restaurants and aboard the Calypso Sunset Dinner Cruise. Experience the island’s culinary and scenic magic in one unforgettable evening.

Combine Maui’s most iconic experiences with a Road to Hana guided tour and the luxurious Calypso Sunset Dinner Cruise. Discover lush rainforests, cascading waterfalls, and gourmet dining against a stunning sunset backdrop.

Discover the magic of Maui’s whale season with the perfect pairing: a daytime whale-watching tour followed by an enchanting Maui Dinner Cruise and Sunset Sail. Witness majestic marine life and enjoy a delicious meal under Maui’s vibrant evening skies.

Make this Thanksgiving unforgettable by setting sail on a family-friendly sunset cruise in Maui. Enjoy a unique way to celebrate the holiday with stunning ocean views, delicious dining, and meaningful family time. Discover why Maui’s sunset sails are perfect for creating lasting holiday memories with loved ones.

Experience the magic of Maui’s winter sunsets and catch unforgettable whale sightings on a sunset sail. Join Teralani or Pacific Whale Eco-Adventures for a scenic and eco-conscious cruise, where the vibrant sky and ocean giants come together to create memories that last a lifetime.

Explore Maui’s lesser-known sunset sail spots, where quiet bays, hidden beaches, and remote cliffs offer a more personal and tranquil way to enjoy the island’s stunning sunsets. Discover Maui’s hidden gems and set sail for an off-the-beaten-path adventure.