Looking for a private boat charter on Maui? Whether you’re planning a family gathering, birthday celebration, corporate outing, group snorkeling adventure, or simply want the boat to yourselves, a private charter with Trilogy Excursions gives you the freedom to experience Maui from the water on your own terms.

With more than 50 years of sailing around Maui and Lāna‘i, Trilogy can help you create a private experience designed around your group. From sunset sails and snorkeling adventures to custom itineraries, here are answers to some of the most common questions we receive about booking a private charter on Maui.

Planning a wedding or wedding-week event? We have a separate guide just for you: → Read our Maui Wedding Charter FAQ

If you still have questions after reading this guide, free to contact our office, or drop a comment at the bottom of this post and we will reply to you as soon as possible!

Private Charter FAQ

What types of private charters does Trilogy offer?

Trilogy offers a variety of private sailing experiences that can be customized for your group. Many of the excursions offered on our website can also be booked as private charters, giving your group the boat and crew to yourselves along with more flexibility to create the experience you’re looking for. To see all of our regular tour options, click here.

Popular private charter options include:

Sunset Sails: Perfect for romantic evenings or group celebrations, featuring Maui’s golden-hour views and a chef-prepared dinner.
Snorkeling Adventures: Explore vibrant reefs and swim alongside tropical fish and sea turtles.
Seasonal Whale Watching: From December to April, witness humpback whales in their natural habitat.
Custom Itineraries: Want something unique? We’ll help you design a day that combines snorkeling, sailing, and dining—all tailored to your preferences.

How many guests can a private charter accomodate?

Our fleet of sailing catamarans can accommodate everything from small, intimate groups to larger gatherings.

Guest capacity varies by vessel and the type of charter you choose. Private dinner sails can accommodate up to 36 guests, while other charter configurations may accommodate larger groups.

Planning something even bigger? Ask our team about multi-vessel options.

What’s included in a private charter?

Your private charter experience may include:

A professional Trilogy captain and crew dedicated to your group
Fresh, island-inspired food and dining options
Bar service with cocktails, local beers, wine, and non-alcoholic beverages
Snorkeling equipment and flotation devices for applicable snorkeling charters
Personalized service throughout your experience

Exact inclusions vary depending on the type of private charter you select, so our team can walk you through the options when planning your sail.

How far in advance should I book a private charter on maui?

We recommend booking as early as possible, particularly if you have a specific date, departure time, or vessel in mind.

For peak travel periods, holidays, and special events, planning 6–12 months ahead gives you the best selection of availability. Last-minute private charters may also be possible depending on our sailing schedule and vessel availability.

In some cases, we may be able to accommodate requests with as little as five days’ notice, but availability is not guaranteed. The earlier you reach out, the more options our team will have to create the right experience for your group.

Can we customize the itinierary?

Absolutely! One of the biggest advantages of booking a private charter is the ability to create an experience specifically for your group.

Depending on the charter and conditions, customization may include your departure time, itinerary, food and beverage options, music, photography, and other special touches.

Tell our team what you have in mind, and we’ll help you explore what’s possible.

Can I book a private charter for a birthday, anniversary, or other celebration?

Yes! Private charters are a great option for birthdays, anniversaries, family reunions, milestone celebrations, corporate outings, friend groups, celebrations of life, and other special occasions.

Whether you want a relaxed sunset sail or an active day of snorkeling and sailing, our team can help match your group with the right experience.

Getting married on Maui? Wedding charters have some additional options and considerations. → Visit our Maui Wedding Charter FAQ

Where do trilogy private charters depart from?

Private charter departure locations depend on the itinerary and vessel. Trilogy operates from Mā‘alaea Harbor, Lahaina Harbor and beach-loading departures from Kā‘anapali Beach.

Your charter specialist will confirm the best departure location for your group when planning your experience.

What types of boats does trilogy use for private charters?

Trilogy’s fleet consists of sailing catamarans designed for comfortable days on the water around Maui and Lāna‘i.

Vessel availability and capacity vary depending on your group size and charter itinerary. To see them in detail, click here.

Do private charters include food and drinks?

Food and beverage options depend on the private charter you select. Trilogy offers fresh, island-inspired dining along with bar service on many of our sailing experiences.

When requesting your charter, let our team know what type of experience you’re planning so we can discuss the available menu and beverage options.

Can we snorkel on a private charter?

Yes! If snorkeling is part of your private charter itinerary, Trilogy provides snorkeling equipment and flotation devices for your group.

Can we book a private sunset sail?

Absolutely. A private sunset sail is one of the best ways to enjoy Maui with your own group.

Instead of joining a public excursion, your group can enjoy the catamaran, crew, Maui views, food, and drinks in a private setting. It’s a popular choice for families, friend groups, birthdays, anniversaries, corporate gatherings, and other celebrations.

Can Trilogy accommodate large groups?

Yes. Capacity depends on the vessel and type of charter, and dinner sails have different capacity limits than some of our other private experiences.

For groups that are too large for a single catamaran, multi-vessel options may also be available. Contact our charter team with your estimated guest count, and we can help determine the best setup.

How much does a private charter in maui cost?

Private charter pricing varies depending on several factors, including:

The type and length of the sail
Your group size
Vessel availability
Time of year
Food and beverage selections
Any additional customizations

Because every private charter can be different, the best way to receive accurate pricing is to tell our team a little about the experience you have in mind. To learn more about pricing, request a quote today!

Ready to Plan Your Maui Private Charter?

Whether you’re bringing together family and friends, celebrating a milestone, planning a company outing, or simply looking for a more private way to experience Maui from the water, Trilogy can help create a charter built around your group.

Tell us your preferred date, approximate group size, and what you’d love to do on the water, and our team will help you explore the options.

Request a Custom Private Charter Quote