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:
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.
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
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.