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
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.
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.
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.