Explore Ideas Below on How to Incorporate Trilogy in Your Wedding Week
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.
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.
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.
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.
Welcome Sail: Kick Off Your Wedding Week in Paradise
Photos By: Matias Ezcurra
Start Your Wedding Week Off the Right Way
Your wedding week begins the moment your guests arrive on Maui—and there’s no better way to bring everyone together than with a private Welcome Sail aboard one of Trilogy’s signature catamarans. Let your friends and family mingle, relax, and settle into island time as they soak in beautiful panoramic ocean views, warm trade winds, and classic Trilogy Ho’okipa (hospitality).
A Welcome Sail sets an unforgettable tone: joyful, relaxed, and full of aloha.
What Your Welcome Sail Includes:
Elevated island Ho’okipa
Our crew specializes in the perfect balance of attentive service and laid-back Maui charm. From boarding to docking, your guests are welcomed like ‘ohana.
Private Sailing catamaran
Create a shared memory right from the start. Enjoy spacious decks, comfortable seating, and a smooth, scenic cruise along Maui’s or/and Lanai’s coastline.
Sunset or daytime options
Plan a golden-hour sail to dazzle your guests, welcoming everyone with a breath-taking Maui sunset. Or a relaxed daytime cruise / snorkeling sail to jump right into the adventure. Both are ideal for mingling, meeting new friends, and kicking off the festivities.
Customizable menus & premium bar
Choose from curated island pupus, signature cocktails, local craft beverages, and optional upgrades for full-service dining. We can match your wedding theme or create a customized menu experience.
Icebreakers made easy
A shared sail is the perfect setting for your two sides of the family to meet, mingle, and connect before the big day—no awkward introductions required.
Why Couples Love Hosting a Welcome Sail:
Optional Enhancements include but are not limited to:
Live music or customized playlist
Signature “couple’s cocktail”
Custom signage or décor
Welcome gifts or lei greeting
Professional photo or video coverage
It gets everyone into the spirit of your wedding week
It offers a unique, quintessentially Maui experience
It gives guests a chance to relax after traveling
It replaces or enhances a traditional welcome party
It creates effortless interaction between families and friends
Trilogy’s 50+ years of sailing expertise and renowned hospitality ensure that your welcome event feels seamless, warm, and elevated.
An Unforgettable Start to an Unforgettable Week
Your wedding week should start with a moment that feels magical—and a Welcome Sail sets the perfect tone. Relax, celebrate, and let us take care of every detail while you enjoy an unforgettable kickoff with the people who matter most.
Bachelor & Bachelorette Sails: Celebrate the Crew That Got You Here
Photos By: Stefan and Audrey
Trade the typical party scene for something truly unforgettable. Trilogy’s Bachelor & Bachelorette Sails offer a sun-soaked, stylish, ocean-side celebration designed for fun, connection, and once-in-a-lifetime memories. Whether you’re craving adventure, relaxation, or a little of both, our private charters set the perfect vibe for your wedding week’s most iconic pre-party.
Bring your crew, your playlist, and your celebratory spirit—Trilogy brings everything else.
Your Celebration, Your Way
Sunset party sail
Turn golden hour into the most gorgeous backdrop imaginable. Think champagne toasts, curated bites, and that warm island glow that makes every moment feel like a postcard.
Daytime party sail
Soak up the Maui sunshine with a refreshing ocean breeze, open deck space for lounging, and a festive atmosphere perfect for group photos, dancing, and toasting the nearlyweds. Whether you just want to cruise on the open water, or make it into a snorkeling experience— we have you covered.
What’s Included:
Signature cocktails & premium beverages
From champagne to local craft favorites to delicious island cocktails, your crew will be well taken care of. Add a custom “His & Hers” (or “Theirs & Theirs”) cocktail for extra fun.
Island-inspired small bites
Enjoy delicious appetizers prepared by Trilogy’s culinary team, with options for full-service dining or upgraded spreads.
Your soundtrack, our surroundings
Connect your playlist or let us help curate the perfect vibe—from tropical chill to full-on celebration mode.
Endless photo oppurtunities
From bow shots to sunset silhouettes, Trilogy’s catamarans offer endless photo ops. Professional photo or video packages can be added too.
Why Couples Love Bachelor & Bachelorette Sails
Optional upgrades
Lei greeting or themed décor
Custom cake or dessert spread
Fun add-ons (floaties, games, champagne spray moments)
Live music or DJ
Transportation arrangements
Photography/videography.
If you have a vision, we’ll help bring it to life—whether it’s classy, splashy, or a little wild.
Ability to get two charters: one for bachelor sail and the other for bachelorette sail.
Unique, elevated alternative to a traditional night out
Perfect for mixed groups who want to celebrate together
Built-in entertainment and stunning scenery
Immersive Maui experience guests will talk about for years
Completely private and customizable
Plus, with Trilogy’s legendary hospitality, every member of your party feels welcomed and celebrated.
Celebrate Your Way, Island Style
Your bachelor or bachelorette celebration should feel effortless, joyful, and completely unforgettable. Let the ocean set the stage and Trilogy handle the details.
After-Wedding Brunch: Your “First Sail After the Veil”
Celebrate the joy of newlywed life with an unforgettable morning experience on the water. Trilogy Weddings & Events invites you to begin your first day as a married couple with our After-Wedding Brunch Sail—your elegant and elevated “First Sail After the Veil.”
Designed for relaxation, connection, and pure romantic bliss, this signature experience offers the perfect opportunity to thank your guests, reminisce about the night before, and savor the first hours of your new chapter together.
Whether you’re dreaming of a brunch sail with chef-crafted cuisine, a scenic coastal cruise, a snorkel adventure, or whale watching (if in season), Trilogy ensures a beautifully curated and completely customizable event to match your wedding vision.
What Does it Include?
Chef-Crafted Brunch Menu
Our in-house catering company, Kapena’s, will prepare a fresh, island-inspired brunch complete with premium ingredients and beautifully presented dishes, served with Trilogy’s renowned level of care.
Exclusive use of a sailing catamaran
Enjoy a private, spacious vessel reserved just for your group, featuring comfortable seating, shaded areas, and panoramic ocean views.
Premium Beverage Service
fully customizable experience
Choose from a relaxed sail, a snorkel excursion at one of Maui’s top reefs, a coastal cruise, or whale watching during peak season—your sail can be as adventurous or as laid-back as you desire.
Treat your guests to sparkling mimosas, tropical cocktails, coffee, juices, and a selection of beer and wine, all served by our professional and attentive team.
Exceptional Trilogy Crew
Music and Ambience
Curate your own playlist and set the mood or enjoy one of the playlists are captain’s already have ready to go— to set a celebratory, relaxed, or romantic tone for your morning on the water.
Our experienced crew provides seamless service, from navigation and safety to thoughtful hospitality and onboard support, ensuring a smooth and enjoyable experience for all.
Optional Enhancements
Couples may personalize their sail with upgraded décor, a professional photographer, specialty pastries or desserts, floral accents, live music, or additional service enhancements. If you can dream it, we can help make it into reality!
Photo Opportunities and Thank-You Moments
The calm morning light and beautiful open ocean create the perfect environment for photos, farewell speeches, and meaningful time with your guests. The perfect way to end your wedding week.
Sail Into Newlywed Bliss
The After-Wedding Brunch Sail offers a refreshing, elegant way to begin your first day as a married couple. With Trilogy’s hospitality, breathtaking views, and the freedom to create the experience that fits you best, your “First Sail After the Veil” promises to be a highlight of your wedding weekend.
Celebrate your new beginning on the water. Your perfect brunch sail awaits.
Why Couples Love the “First Sail After the Veil”
A serene, joyful way to ease out of the wedding festivities
A thoughtful opportunity to thank your guests and spend quality time together
Unique, memorable, and classically Hawaiian
Perfect for adventurous couples and relaxed groups alike
A customizable experience that reflects your personality and style