Captain's Sunset Dinner Sail

Exclusive Captain's Sunset Dinner Sail

A four-course dinner with an unbeatable view! 2-top tables are set for intimacy &  comfort; a private restaurant feel without the crowds aboard our spacious sailing catamaran.  As you are escorted to your table, the evening begins with cocktails and sailing along Maui’s scenic coast.  After mooring in a protected cove, the first course is served.  Our Crew is quick to accommodate your every need and will serve your remaining three courses including your chef-prepared entrée. This is no ordinary dinner! After the sun sets, enjoy starlight sailing and after-dinner drinks.

Ka'anapali Sunset Sail

Exclusive Ka'anapali Sunset Sail

Departing directly from Ka’anapali Beach, climb aboard our luxury sailing catamaran and escape the crowded restaurants onshore. While sipping on premium signature cocktails at your private two-top table, our Crew will serve you delicious plated appetizers, cooked with locally sourced ingredients. As you take in a breathtaking Maui sunset, our Captain will also share stories of our local history and marine life. You’re sure to build lasting memories with this intimate, romantic evening tour!

Ma'alaea Sunset Sail

Exclusive Ma'alaea Sunset Sail

This deluxe Sunset Sail departing out of Ma’alaea Harbor provides our guests with the combination of a famous Maui sunset and 2 rounds (plus dessert!) of delicious plated appetizers. Sip & sail with us on this 2-hour tour, including a deluxe premium bar.   Enjoy the sunset & unobstructed views of Kaho’olawe and Lana’i, two of Maui’s offshore islands, and discover why Trilogy has been voted the #1 sailing company on Maui for over 45 years! 

Exclusive Sunset Whale Watches

Exclusive Sunset Whale Watch Sails

This deluxe Sunset Sail departing out of Ma’alaea Harbor provides our guests with the combination of a famous Maui sunset and 2 rounds (plus dessert!) of delicious plated appetizers. Sip & sail with us on this 2-hour tour, including a deluxe premium bar.   Enjoy the sunset & unobstructed views of Kaho’olawe and Lana’i, two of Maui’s offshore islands, and discover why Trilogy has been voted the #1 sailing company on Maui for over 45 years!