Engagement Sail: Proposals at Sea
A Moment as Endless as the Horizon
Your proposal deserves a setting as unforgettable as the love you’re celebrating. Trilogy’s Engagement Sail offers an intimate, breathtaking experience crafted for one of life’s most meaningful moments.
Whether you’re planning a private, secluded proposal or a celebration with close friends and family, our team ensures every detail is effortless, elegant, and unforgettable.
Your Private Proposal Experience Includes:
Personalized planning support
From timing the perfect moment to orchestrating music, photography, or special surprises, our dedicated event team works with you quietly and discreetly to bring your vision to life.
Exclusive Sailing Catamaran Charter
Escape the crowds with a private sail aboard one of Trilogy’s signature catamarans. Enjoy beautiful panoramic ocean views, gentle trade winds, and the magic of a Maui sunset as your perfect backdrop.
Professional photography add-on
Capture the moment forever. We can arrange a hidden photographer to discreetly document the proposal and transition into a romantic engagement portrait session on deck.
Gourmet island-inspired refreshments
Celebrate with curated drinks and pūpū’s (appetzers) crafted by our onboard culinary team. Custom menus, champagne toasts, and elevated dining enhancements are all available.
Additional romantic touches
Rose petals, custom signage, a dedicated playlist, or family waiting onboard to celebrate—if you can dream it, we can stage it.
Why Propose With Trilogy?
For over 50 years, Trilogy has hosted Maui’s most memorable ocean experiences. Our engagement sails combine the privacy of a charter with the warmth of true Hawaiian hospitality. It’s the perfect way to begin your wedding week—or simply to begin the next chapter of your life together.
Let’s Plan the Proposal of Your Dreams
Your love story is one of a kind—your proposal should be too. Click below to connect with our Trilogy Weddings & Events team and start planning your perfect engagement sail.